Title: 10 Best Hotels in Sleepy Hollow, Chicago for 2026 | Expedia.ca

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## Check prices for these dates

Tonight

[Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-01-30&endDate=2026-01-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-01-31&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Our top choices for Sleepy Hollow hotels

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2556x3y3-aad44a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/d34c171a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (2 Room)](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2561x3y0-7e662cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Claridge House Chicago, Tapestry Collection by Hilton

[](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information)

Gold Coast, 13.8 km from Sleepy Hollow

9.0/10

Wonderful

(1,519 reviews)

"Great location, friendly staff and nice room"

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

Srinivasa

CA $76

CA $129 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Claridge-House-Chicago.h22684.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)

![2 restaurants, breakfast, lunch, dinner served; Latin American cuisine](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Streeterville, 14.4 km from Sleepy Hollow

9.4/10

Exceptional

(2,341 reviews)

"Great stay"

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

Blake

CA $143

CA $214 total

includes taxes & fees

Feb 10 - Feb 11

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

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w3837h2557x3y3-ef0f356b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/95b10764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/8b216cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/3932c1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Thompson Chicago, by Hyatt

[](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information)

Gold Coast, 13.6 km from Sleepy Hollow

9.2/10

Wonderful

(1,314 reviews)

"great stay"

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

Loan

CA $182

CA $254 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information)

![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/24000000/23360000/23355000/23354943/8da50482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/24000000/23360000/23355000/23354943/ccac7aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/24000000/23360000/23355000/23354943/5c662e9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/24000000/23360000/23355000/23354943/c9538f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Moxy Chicago Downtown

[](https://www.expedia.ca/Chicago-Hotels-Moxy-Chicago-Downtown.h23354943.Hotel-Information)

River North, 12.5 km from Sleepy Hollow

9.4/10

Exceptional

(879 reviews)

"Clean, friendly staff, and excellent location "

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

Paulina

CA $138

CA $162 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Moxy-Chicago-Downtown.h23354943.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/6b730d6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Two Bedroom Suite | Dining room](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/c0679d99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/19637b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago Fulton Market

[](https://www.expedia.ca/Chicago-Hotels-Level-Chicago-Fulton-Market.h95823687.Hotel-Information)

West Loop, 11.5 km from Sleepy Hollow

9.2/10

Wonderful

(393 reviews)

"The hotel in it’s entirety was better than advertised "

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

Eric

[](https://www.expedia.ca/Chicago-Hotels-Level-Chicago-Fulton-Market.h95823687.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/a5563f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6bab11c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Suite, 1 Bedroom, 1 King Bed, 1 Sofabed](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/b60fd014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/2f29850e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sofitel Chicago Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Sofitel-Chicago-Magnificent-Mile.h864219.Hotel-Information)

13.4 km from Sleepy Hollow

9.4/10

Exceptional

(2,324 reviews)

"The rooms are beautiful and the staff is wonderful."

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

Melissa

CA $228

CA $307 total

includes taxes & fees

Jan 31 - Feb 1

[](https://www.expedia.ca/Chicago-Hotels-Sofitel-Chicago-Magnificent-Mile.h864219.Hotel-Information)

![2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/8d2143ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/52469d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bars/lounges, piano bar](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/f598823d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/w1101h1283x0y1-ef09926c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hoxton Chicago

[](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information)

11 km from Sleepy Hollow

9.0/10

Wonderful

(1,001 reviews)

"Amazing, I loved my stay"

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

Valerie

[](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1760900/1760845/c91f6cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1770000/1760900/1760845/w3996h2667x0y0-c84e78c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view](https://images.trvl-media.com/lodging/2000000/1770000/1760900/1760845/8052cf6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1770000/1760900/1760845/1885ffcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Springhill Suites by Marriott Chicago Downtown/ River North

[](https://www.expedia.ca/Chicago-Hotels-Springhill-Suites-By-Marriott-Chicago-Downtown-River-North.h1760845.Hotel-Information)

River North, 12.6 km from Sleepy Hollow

9.4/10

Exceptional

(1,033 reviews)

" Clean rooms Hot shower great after a freezing cold day Staff all polite and helpful Great location "

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

John

CA $143

CA $168 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Springhill-Suites-By-Marriott-Chicago-Downtown-River-North.h1760845.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/3ff1c0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/8c126093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/87fb06ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/7b541fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Chicago West Loop Fulton Market Area

[](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-Downtown-West-Loop.h15849775.Hotel-Information)

11.4 km from Sleepy Hollow

9.2/10

Wonderful

(1,001 reviews)

"Nice hotel and staff. "

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

Wendy

CA $171

CA $201 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-Downtown-West-Loop.h15849775.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/7923a1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/83c82ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 1 King Bed (View)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bd7c3671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bc9a17b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### citizenM Chicago Downtown

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

Theatre District, 12.7 km from Sleepy Hollow

9.4/10

Exceptional

(4,216 reviews)

"Very nice Hotel, great atmosphere friendly staff. I had a great stay!"

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

Lucie Saint Jean

CA $139

CA $163 total

includes taxes & fees

Feb 4 - Feb 5

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

![City view from property](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/e4567f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/db5b7e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/fa1d7c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt House Chicago West Loop

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information)

10.6 km from Sleepy Hollow

8.8/10

Excellent

(1,171 reviews)

"Staff is wonderful, nice clean rooms, centrally located, loved staying here. "

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

Cassandra

CA $175

CA $206 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information)

![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Water view](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/0b2651d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite, 1 King Bed, Accessible | Living room](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/72c3363f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LondonHouse Chicago, Curio Collection by Hilton

[](https://www.expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

The Loop, 12.7 km from Sleepy Hollow

9.4/10

Exceptional

(3,574 reviews)

"Staff was kind and it was at a great location! "

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

Kiran

CA $209

CA $245 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/54e0cfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/f0cafd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/d35b9e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chicago Hotel Collection Ambassador Gold Coast

[](https://www.expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information)

Gold Coast, 13.9 km from Sleepy Hollow

8.2/10

Very good

(1,280 reviews)

"Great hotel at an affordable price "

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

Dhruv

CA $117

CA $138 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/f36e2ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/66eb210e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d288265e.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)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

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

River North, 12.9 km from Sleepy Hollow

8.6/10

Excellent

(4,345 reviews)

"All things about this hotel was good from the location to the staff"

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

Cisco

CA $115

CA $135 total

includes taxes & fees

Feb 5 - Feb 6

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

![Lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/d70c748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/fd4d7555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/df6e8a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/44865590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Radisson Blu Aqua Hotel Chicago

[](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information)

12.9 km from Sleepy Hollow

8.6/10

Excellent

(1,841 reviews)

"Beautiful hotel nice friendly staff. I loved the view. "

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

Nicole

CA $212

CA $285 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/220cf128.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/1000000/890000/886400/886306/178af231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/5e20364f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/3c43769a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ACME Hotel Chicago, Outset Collection by Hilton

[](https://www.expedia.ca/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information)

River North, 12.9 km from Sleepy Hollow

9.0/10

Wonderful

(1,947 reviews)

"Very convenient place to stay friendly and helpful staff."

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

Rick

CA $110

CA $129 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed (Deluxe King)](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/433123ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/1fffa05c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/ecc355f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Emily Hotel

[](https://www.expedia.ca/Chicago-Hotels-Ace-Hotel-Chicago.h19381112.Hotel-Information)

11.1 km from Sleepy Hollow

9.2/10

Wonderful

(1,300 reviews)

"Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again. "

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

Mary

CA $169

CA $198 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Chicago-Hotels-Ace-Hotel-Chicago.h19381112.Hotel-Information)

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

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/a08c52fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.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)

### DoubleTree by Hilton Chicago - Magnificent Mile

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

Streeterville, 13.4 km from Sleepy Hollow

8.8/10

Excellent

(2,270 reviews)

"amazing stay"

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

Anani

CA $115

CA $135 total

includes taxes & fees

Feb 5 - Feb 6

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

![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/2435ca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/0ea4e737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/be69fa71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Embassy Suites by Hilton Chicago Downtown Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information)

Streeterville, 13.3 km from Sleepy Hollow

8.2/10

Very good

(2,804 reviews)

"Great hotel staff and location. "

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

Jacqueline

CA $150

CA $215 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.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)

![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.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/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

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

Streeterville, 13.4 km from Sleepy Hollow

8.6/10

Excellent

(3,063 reviews)

"Great location and friendly staff. "

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

Pablo

CA $123

CA $144 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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=2026-02-13&endDate=2026-02-14&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
- O'Hare

![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)

![Rosemont](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191807-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191915-Rosemont.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Rosemont featuring street scenes and flowers as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191914-Rosemont.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Rosemont featuring street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191913-Rosemont.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Rosemont](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191911-Rosemont.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635074842747)

![O'Hare map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:kob_G%60rvwOqeEoAa%5DcHiNiH%7BIcKkg%40au%40%7BB_y%40i%40ooAiBqkAeFqHo%40%7DOkDx%40sB%7DBRcP%60nA%7DElWou%40vK%7Dl%40%7Be%40G%7DNjEGaQtd%40gOx_%40uHvOoxCpSsIp%7BC_Ed%40vXd%7D%40Hba%40o%40ve%40aDjAdfBiZfGy%5DzJo%5EbAwFnAaRxXkx%40vCp%40dl%40Knn%40%7EL%7EH%7CQdPjP%7ERpE_S%60q%40vR%7E%5EbU%7DYzz%40uSZh%40vZy%40nWyFj%5EeRd%7E%40_%40%7Eu%40oC%7Ep%40kLhFwNtB&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=-bZOHa3BE39TNl-SIM1ovW8-8lc=)

### O'Hare

Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635074842747)

## Top Sleepy Hollow Hotel Reviews

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg)

### Aloft Chicago Mag Mile

10/10 Excellent

"Great location and friendly staff. "

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

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg)

### The Wade

10/10 Excellent

"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "

[](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"What great value i found at the River. Spotless room, friendly and attentive staff. Can't wait to return!"

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

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

### Hotel Riu Plaza Chicago

10/10 Excellent

"Love the place! Great breakfast buffet. The room was clean, service was great, and great"

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

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

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

10/10 Excellent

"Great experience with no problems"

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

![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg)

### Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent

"Great location"

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"We arrived later than planned due to the weather, but the front desk staff greeted us warmly and made us feel welcome right away. They were very friendly and kind. As always, the room was clean this has been consistent every time we stay. The bed and pillows were comfortable, and I absolutely loved the shower. Overall, it’s an all-around great hotel, and we always enjoy our stay here."

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

![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg)

### DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent

"Spotless"

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

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

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Excellent "

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

## Frequently asked questions

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

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

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

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

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

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