Title: 10 Best Hotels in Sleepy Hollow, Chicago for 2025 | Expedia.ca

  

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# Hotels in Sleepy Hollow, Chicago

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## Go beyond your typical stay in Sleepy Hollow

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=SPA_ON_SITE)

Apart hotel

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APART_HOTEL)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&travelerType=family_friendly)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=POOL)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APARTMENT)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=PETS)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=CONDO)

Waterpark

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Sleepy Hollow hotels and places to stay

![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Hotel

The Loop, 12.7 km from Sleepy Hollow

8.8/10

Excellent

(4763)

"Great area at a good price. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laura

CA $134

CA $158 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/06b28362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eurostars Magnificent Mile

River North, 13 km from Sleepy Hollow

9.0/10

Wonderful

(3080)

"Excellent stay, close to everything and the staff was super nice "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kieata

CA $167

CA $196 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

8.8/10

Excellent

(2117)

"Great stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melinda

CA $144

CA $169 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

8.6/10

Excellent

(2868)

"Had a great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Josh

CA $151

CA $177 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.4 km from Sleepy Hollow

9.4/10

Exceptional

(2230)

"Rooms were clean with a great view of the lake and the city "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nathan

CA $135

CA $206 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago

The Loop, 11.7 km from Sleepy Hollow

8.4/10

Very good

(2271)

"Staff was wonderful, property was clean and welcoming. Great amenities for families and great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephen

CA $158

CA $227 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bb272e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

9.4/10

Exceptional

(4026)

"Great place to stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

sherry

CA $159

CA $186 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information)

![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/fb80c7da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/5b3c70b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/c46ad167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

9.0/10

Wonderful

(1636)

"Staff was friendly upon check in and the premise was very clean."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelan

CA $142

CA $167 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, City View | Living area](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

8.0/10

Very good

(9631)

"Area is great and walkable distance to touring areas. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alejandro

CA $131

CA $154 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/172457c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

9.0/10

Wonderful

(3201)

"Overall it was a great place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Edward

CA $153

CA $180 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b6152ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/520a670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f9eed5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western River North Hotel

River North, 12.6 km from Sleepy Hollow

7.8/10

Good

(1004)

"Great stay"

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Bart

CA $141

CA $166 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freehand Chicago

River North, 12.9 km from Sleepy Hollow

8.0/10

Very good

(2546)

"Very accessible location and amazing staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Fatima

CA $107

CA $151 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/b9be2277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

River North, 12.9 km from Sleepy Hollow

8.4/10

Very good

(4127)

"This hotel had a great location to shopping and several enjoyable restaurants."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

laura

CA $158

CA $186 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f5c52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Riu Plaza Chicago

Streeterville, 13.2 km from Sleepy Hollow

9.4/10

Exceptional

(2688)

"Great place to stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Larry William

CA $170

CA $239 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/cbeee5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/0c9aebe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/2b6118c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/9ab0dcf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FOUND Hotel Chicago River North

River North, 12.6 km from Sleepy Hollow

8.2/10

Very good

(296)

"Perfect location! Tons of restaurants and shopping nearby! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

MaryJane

CA $106

CA $125 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/3df6d1fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/41b8776a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/a1af2bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/3a3575cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Regal Inn - Chicago O'Hare Airport

17.1 km from Sleepy Hollow

8.0/10

Very good

(1004)

"Inexpensive, close to the airport, clean"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jay

CA $85

CA $91 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Chicago-Hotels-Regal-Inn-Chicago-OHare-Airport.h1305402.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/938c3a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/39b9d2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/cc07f74b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/0d409450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Chicago O'Hare Airport

27.1 km from Sleepy Hollow

7.6/10

Good

(1483)

"I liked that people where super helpful, had its own shuttle and indoor pool"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Valeria

CA $97

CA $109 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Super-8-By-Wyndham-Chicago-OHare-Airport.h440405.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f3b451c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f906be7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/ca3aaed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f9eb35b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Suites Chicago O'Hare Airport

18.7 km from Sleepy Hollow

8.2/10

Very good

(2718)

"Clean quiet and great location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cyrus

CA $105

CA $120 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Chicago-Hotels-Comfort-Suites-Schiller-Park-Chicago-OHare-Airport.h664918.Hotel-Information)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c8177aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/a23482f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitehall Hotel, BW Premier Collection

Streeterville, 13.5 km from Sleepy Hollow

8.2/10

Very good

(3665)

"Excellent location, old style hotel with an independent feel. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jose

CA $119

CA $139 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/05f95ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silversmith Hotel Chicago Downtown

Theatre District, 12.2 km from Sleepy Hollow

9.4/10

Exceptional

(2030)

"Great place to stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl

CA $148

CA $216 total

includes taxes & fees

Nov 27 - Nov 28

[](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&regionId=6132427&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.

-   Downtown Chicago
-   Magnificent Mile
-   The Loop
-   River North
-   Lincoln Park

![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191755-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Downtown Chicago which includes a high-rise building and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332087-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Downtown Chicago featuring signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332073-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Downtown Chicago featuring a city and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332084-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6350699)

![Downtown Chicago map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:uxq%7EFvjavOurAq%40mA%7DgDuTtO%7BFzJuOr%40mk%40z_%40MifBum%40%7EAGmaAx%7EAopCna%40uM%7EoC%7C%7DAx%40%7CkCnk%40yAy%40n%7B%40gt%40dE%7Bg%40pFo%40%60%7EB&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XpzTv33-iXOpq3icViGLtz3e_jE=)

### Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6350699)

![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543374-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Magnificent Mile - River North showing signage and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191832-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Magnificent Mile - River North which includes street scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191836-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Magnificent Mile - River North showing a hotel, a city and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24572-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=800025)

![Magnificent Mile map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:gnt%7EF%60dyuOugAK%3FcChgALJ%60C&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=eJaOW3wrdH9kguwKvLeM9_7UbMs=)

### Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=800025)

![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543387-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543370-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![The Loop - Downtown featuring a river or creek and a ferry](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191752-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192010-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=800024)

![The Loop map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:syr%7EFxx%7BuOqa%40mAeEqK_%40sp%40kG%7BKvAwg%40Xok%40%7C_%40x%40xF%7EPtlAi%40dCh%40DzOxDxCDnbBkNr%40e%5E%7EEkKzGiVfC&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XwfHKgKFqor-NvwNZdw8nZOnNbI=)

### The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=800024)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543384-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Shops at North Bridge which includes central business district, a city and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191962-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191756-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Shops at North Bridge showing a city, central business district and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191961-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6350695)

![River North map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:%7B%7Cu%7EFl_%7DuOWcpA%7CECQ%7Db%40xi%40w%40nGbNJ%7Ep%40xCbHxAdBcB%7ECuAhA%7DKdCyGvFiGdDsD%7CDeCzEwBfBoN%5E&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=pVk_WdkeHd9iD-9kitVtoqcFN2A=)

### River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6350695)

![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24578-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Lincoln Park Zoo showing autumn colours and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26661-Lincoln-Park-Zoo.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24579-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago History Museum featuring interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24583-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6059328)

![Lincoln Park map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:u%7E%7C%7EFhscvO%40%7DMjAWEyE_JFsDaCAl%40qDD%3F%7DBjU_%40AkAiAQ%40aWbAKAyFqALQeJzAIKaNiAJOgUTi%40%7E%40KEgF_BD%3FuMbBMc%40_NiAAI%7DImAIKmB%7CAQMeVxAKQ%7BOwGaCnCQHeCtBKFgC%7DAUSaGbBIx%40i%60Axp%40mMbD%7EGpa%40%7DJpR%7DM%60NgVzGrLV%60n%40mJ%7EEh%40%60AfIKClIuCNp%40xRrBWl%40b%7EAoEJoElF%7CArEjIiGKpNoVzJqItQvCfKsArA%7DL%60FuXhVm%40%60NaKhR%7BK%7CAcFbKiAzFsK_MqLbN%7DAJ&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=KktfaLNeQ_9ZFVphttKdls3N5TA=)

### Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6059328)

## Top Sleepy Hollow Hotel Reviews

![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"i have been visiting chicago frequently over the last few months and this hotel thus far has exceeded any hotel stay that ive had. the staff was amazing and the location and room was great for the money spent. i will return "

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![citizenM Chicago Downtown](//images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg)

### citizenM Chicago Downtown

10/10 Excellent

"Closer parking or vale"

[](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information)

![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg)

### The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Staff was very nice and the hotel is near everything "

[](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"Floor-to- ceiling windows providing beautiful views of the Lake and City skyline (and windowseat) were very nice. Location was nice. Room was quiet. Bed was very comfortable. Staff was courteous and helpful."

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg)

### Warwick Allerton - Chicago

10/10 Excellent

"Computers need updates. Staff great."

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"Great"

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"The only negative experience was seeing the Disgraceful Trump Tower across the street. "

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"Breakfast was great, staff is always amazing. Only place I like staying in Chicago!"

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Pendry Chicago](//images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg)

### Pendry Chicago

10/10 Excellent

"We loved the Pendry!"

[](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information)

## Frequently asked questions

### What are the best family hotels in Sleepy Hollow?

> The [Carlton Inn Midway](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) in Chicago is a fantastic option for families seeking comfort and convenience during their travels. This family-friendly hotel offers complimentary cribs and free stays for children, making it an excellent choice for those traveling with little ones.

### What hotels in Sleepy Hollow offer free breakfast?

> [Carlton Inn Midway](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) in Chicago is an excellent choice for travellers seeking a family-friendly atmosphere with convenient amenities. This welcoming hotel offers a complimentary continental breakfast, ensuring that families can start their day off right without any hassle. The 24-hour airport shuttle service makes it easy for guests to navigate their travel plans, great for families arriving with little ones in tow.

### Can I cancel my hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Sleepy Hollow hotel for you.

### How can I save on a Sleepy Hollow hotel booking with Expedia?

> Before booking your Sleepy Hollow hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.

### How much is the nightly rate at a Sleepy Hollow hotel?

> Hotel prices in Sleepy Hollow often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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-   [Forest View Hotels](https://www.expedia.ca/Forest-View-Hotels.d6132093.Travel-Guide-Hotels)
-   [Gage Park Hotels](https://www.expedia.ca/Gage-Park-Chicago-Hotels.0-n6132375-0.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Cheap-Hotels.0-n6132357-0-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Parking in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132357-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels)
-   [Romantic Hotels in Garfield Ridge](https://www.expedia.ca/Garfield-Ridge-Chicago-Hotels-Romantic-Hotel.0-n6132357-0-tRomanticHotel.Travel-Guide-Filter-Hotels)
-   [Heart of Chicago Hotels](https://www.expedia.ca/Heart-Of-Chicago-Chicago-Hotels.0-n553248635976482355-0.Travel-Guide-Filter-Hotels)
-   [Lavergne Hotels](https://www.expedia.ca/Lavergne-Hotels.d6132171.Travel-Guide-Hotels)
-   [Lawndale Hotels](https://www.expedia.ca/Lawndale-Chicago-Hotels.0-n553248635976384042-0.Travel-Guide-Filter-Hotels)
-   [Little Village Hotels](https://www.expedia.ca/Little-Village-Chicago-Hotels.0-n6132436-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Marquette Park](https://www.expedia.ca/Marquette-Park-Hotels.0-l507385-0.Travel-Guide-Filter-Hotels)
-   [Mckinley Park Hotels](https://www.expedia.ca/McKinley-Park-Chicago-Hotels.0-n6132389-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Midway Intl.](https://www.expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Midway Station](https://www.expedia.ca/Midway-Station-Hotels.d6211025.Travel-Guide-Hotels)
-   [New City Hotels](https://www.expedia.ca/New-City-Chicago-Hotels.0-n6132388-0.Travel-Guide-Filter-Hotels)
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-   [Hotels near Pulaski Station](https://www.expedia.ca/Pulaski-Station-Hotels.d6211019.Travel-Guide-Hotels)
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-   [Stickney Hotels](https://www.expedia.ca/Stickney-Hotels.d6132201.Travel-Guide-Hotels)
-   [Summit Hotels](https://www.expedia.ca/Summit-Hotels.d177671.Travel-Guide-Hotels)
-   [West Lawn Hotels](https://www.expedia.ca/West-Lawn-Chicago-Hotels.0-n6132413-0.Travel-Guide-Filter-Hotels)

-   [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
-   [Flights to Midway Intl.](https://www.expedia.ca/Cheap-Flights-To-Midway-Intl.d5719117.Travel-Guide-Flights)
-   [Flights from Midway Intl.](https://www.expedia.ca/lp/airports/mdw/flights-from-midway-intl-airport)
-   [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw)
-   [Porter Airlines Ottawa (YOW) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-macdonald-cartier-intl-to-midway-intl/pd/yow/mdw)
-   [Porter Airlines Montreal (YUL) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-pierre-elliott-trudeau-intl-to-midway-intl/pd/yul/mdw)
-   [Porter Airlines Thunder Bay (YQT) to Chicago (MDW) flights](https://www.expedia.ca/lp/flight-routes/porter-airlines-from-thunder-bay-intl-to-midway-intl/pd/yqt/mdw)
-   [Flights from Lake Of The Ozarks (AIZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/aiz/mdw/lake-of-the-ozarks-to-chicago)
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-   [Flights from Bellingham (BLI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bli/mdw/bellingham-to-chicago)
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-   [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago)
-   [Flights from Baltimore (BWI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bwi/mdw/baltimore-to-chicago)
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-   [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago)
-   [Flights from Newark Liberty Intl. Airport (EWR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ewr/mdw/newark-liberty-intl-airport-to-chicago)
-   [Flights from Fishers Island (FID) to Chicago (MDW)](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago)
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-   [Flights from Omaha (OMA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago)
-   [Flights from Ontario (ONT) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ont/mdw/ontario-to-chicago)
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-   [Flights from Philadelphia (PHL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago)
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-   [Flights from Ottawa (YOW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago)
-   [Flights from Peterborough (YPQ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago)
-   [Flights from Québec (YQB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago)
-   [Flights from Windsor (YQG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqg/mdw/windsor-to-chicago)
-   [Flights from Moncton (YQM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqm/mdw/moncton-to-chicago)
-   [Flights from Thunder Bay (YQT) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqt/mdw/thunder-bay-to-chicago)
-   [Flights from Sudbury (YSB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago)
-   [Flights from Timmins (YTS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago)
-   [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago)
-   [Flights from Montreal (YUL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago)
-   [Flights from Vancouver (YVR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yvr/mdw/vancouver-to-chicago)
-   [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago)
-   [Flights from Saskatoon (YXE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yxe/mdw/saskatoon-to-chicago)
-   [Flights from North Bay (YYB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyb/mdw/north-bay-to-chicago)
-   [Flights from Calgary (YYC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago)
-   [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

-   [Ace Rental Cars in Midway Intl.](https://www.expedia.ca/Ace-Car-Rentals-In-Midway-Intl.d5719117-c2.Car-Rental-Guide-Suppliers)
-   [Alamo Rent A Car Rental Cars in Midway Intl.](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Midway-Intl.d5719117-c6.Car-Rental-Guide-Suppliers)
-   [Budget Rental Cars in Midway Intl.](https://www.expedia.ca/Budget-Car-Rentals-In-Midway-Intl.d5719117-c39.Car-Rental-Guide-Suppliers)
-   [Rental cars Midway Intl. airport](https://www.expedia.ca/Car-Rentals-In-Midway-Intl.d5719117.Car-Rental-Guide)
-   [Dollar Rent A Car Rental Cars in Midway Intl.](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Midway-Intl.d5719117-c43.Car-Rental-Guide-Suppliers)
-   [Enterprise Rental Cars in Midway Intl.](https://www.expedia.ca/Enterprise-Car-Rentals-In-Midway-Intl.d5719117-c15.Car-Rental-Guide-Suppliers)
-   [Express Travel Group Rental Cars in Midway Intl.](https://www.expedia.ca/Express-Travel-Group-Car-Rentals-In-Midway-Intl.d5719117-c1124.Car-Rental-Guide-Suppliers)
-   [Hertz Rental Cars in Midway Intl.](https://www.expedia.ca/Hertz-Car-Rentals-In-Midway-Intl.d5719117-c40.Car-Rental-Guide-Suppliers)
-   [Premium Car Rentals near Midway Intl.](https://www.expedia.ca/Premium-Car-Rentals-In-Midway-Intl.d5719117-tPremium.Car-Rental-Guide-Class)
-   [Van Car Rentals near Midway Intl.](https://www.expedia.ca/Van-Car-Rentals-In-Midway-Intl.d5719117-tVan.Car-Rental-Guide-Class)

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