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

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# Hotels in Sleepy Hollow, Chicago 

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## Check prices for these dates

Tonight

[Jan 2 - Jan 3](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-01-02&endDate=2026-01-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-01-03&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Our top choices for Sleepy Hollow hotels

![Room, 2 Queen Beds, Corner (View)](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/w4000h2662x0y0-8993d93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/d1c3823c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/f4b54642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/7d83db78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Downtown River North

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Downtown-River-North.h5461400.Hotel-Information)

River North, 12.6 km from Sleepy Hollow

9.4/10

Exceptional

(1176)

"Great stay!"

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

Tea

CA $146

CA $171 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Downtown-River-North.h5461400.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d.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)

![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)

![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

(3494)

"Great hotel! "

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

Kianna

CA $190

CA $223 total

includes taxes & fees

Jan 12 - Jan 13

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

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/1272603a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/4d5fc313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/12c82a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### L7 Chicago by LOTTE

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

Theatre District, 12.6 km from Sleepy Hollow

9.6/10

Exceptional

(3474)

"Amazing place to stay and super accommodating "

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

Carson

CA $184

CA $215 total

includes taxes & fees

Jan 14 - Jan 15

[](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![49-inch flat-screen TV with digital channels, TV, DVD player](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/d3bfa994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/7e3f0364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/8abc6396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### theWit Chicago, a Hilton Hotel

[](https://www.expedia.ca/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information)

Theatre District, 12.4 km from Sleepy Hollow

9.0/10

Wonderful

(1001)

"Great views and super comfortable bed. "

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

Keely

CA $201

CA $277 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/6bc4b464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/fbced2d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/f66560b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Omni Chicago Hotel

[](https://www.expedia.ca/Chicago-Hotels-Omni-Chicago-Suites-Magnificent-Mile.h11076.Hotel-Information)

Magnificent Mile, 13.3 km from Sleepy Hollow

9.2/10

Wonderful

(1659)

"Great place to stay "

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

Juliet

CA $218

CA $297 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Chicago-Hotels-Omni-Chicago-Suites-Magnificent-Mile.h11076.Hotel-Information)

![American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/ab309a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/69e6751f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/64fc97f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/a073ef3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Godfrey Hotel Chicago

[](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information)

River North, 12.8 km from Sleepy Hollow

8.6/10

Excellent

(1968)

"The room was nice, the area was perfect for walking distance for food and activities. "

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

Alexis

CA $113

CA $165 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6efd5146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wade

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

Streeterville, 13.8 km from Sleepy Hollow

8.4/10

Very good

(1565)

"Great staff and great location. "

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

Joe

CA $127

CA $149 total

includes taxes & fees

Jan 8 - Jan 9

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

![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/dd2b4128.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)

![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6b3ccd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/57bcab8a.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

(2291)

"great hotel"

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

Andrea

CA $220

CA $299 total

includes taxes & fees

Jan 10 - Jan 11

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

![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/63edec8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/186b641d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/cc228cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Chicago Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

Streeterville, 13.3 km from Sleepy Hollow

9.0/10

Wonderful

(1056)

"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "

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

Rebecca

CA $134

CA $198 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/bebf91fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/c8521e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/fbf72db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Swissotel - Chicago

[](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

13 km from Sleepy Hollow

9.0/10

Wonderful

(3083)

"Amazing staff and location beautiful hotel "

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

RANDIE

CA $156

CA $224 total

includes taxes & fees

Jan 5 - Jan 6

[](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/2489547a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/17f1a3a3.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/1000000/50000/50000/49985/63f719c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/3be95933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Saint Clair- Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-The-St-Clair-Hotel-Magnificent-Mile.h49985.Hotel-Information)

Streeterville, 13.3 km from Sleepy Hollow

8.4/10

Very good

(1809)

"Very clean and comfortable hotel!"

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

HYUNJI

CA $94

CA $112 total

includes taxes & fees

Jan 7 - Jan 8

[](https://www.expedia.ca/Chicago-Hotels-The-St-Clair-Hotel-Magnificent-Mile.h49985.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9833019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/325381ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/3f6518d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/661195c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ivy Boutique Hotel

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

Streeterville, 13.4 km from Sleepy Hollow

8.8/10

Excellent

(1061)

"My favorite hotel for a staycation"

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

SABRINA L

CA $104

CA $122 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/24000000/23360000/23355000/23354943/1018f074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/24000000/23360000/23355000/23354943/424d7be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/24000000/23360000/23355000/23354943/ce2f2b32.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

(863)

"Great hotel, lots of fun and great location! "

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

Amber

CA $140

CA $164 total

includes taxes & fees

Jan 11 - Jan 12

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

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.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)

### Hilton Chicago/Magnificent Mile Suites

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

Streeterville, 13.8 km from Sleepy Hollow

9.0/10

Wonderful

(3653)

"Great place to stay "

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

RaShawna

CA $123

CA $144 total

includes taxes & fees

Jan 11 - Jan 12

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

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Felix River North/Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

River North, 12.9 km from Sleepy Hollow

8.2/10

Very good

(2492)

"The room was amazing and the customer service was great!"

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

Chelsi

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/86b2dc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/22705c69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/289caf93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Tapas bar](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/e6c4a358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### AC Hotels by Marriott Chicago Downtown

[](https://www.expedia.ca/Chicago-Hotels-AC-Hotels-By-Marriott-Chicago-Downtown.h1110039.Hotel-Information)

River North, 13.1 km from Sleepy Hollow

8.8/10

Excellent

(1006)

"Very nice cozy hotel "

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

CARLA

CA $138

CA $162 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Chicago-Hotels-AC-Hotels-By-Marriott-Chicago-Downtown.h1110039.Hotel-Information)

![Snack bar](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/4844f60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/0afe31db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/1679ab90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/w1584h1367x232y0-cd23229b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cambria Hotel Chicago Loop - Theatre District

[](https://www.expedia.ca/Chicago-Hotels-Cambria-Hotel-Chicago-Loop-Theatre-District.h18057374.Hotel-Information)

Theatre District, 12.2 km from Sleepy Hollow

8.8/10

Excellent

(1483)

"Great room and friendly staff. Great place to stay for the price. I Would definitely recommend this hotel to a friend. "

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

Timothy

CA $123

CA $144 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Cambria-Hotel-Chicago-Loop-Theatre-District.h18057374.Hotel-Information)

![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)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/128dfde4.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

(4306)

"Amazing staff and perfect location "

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

Brandi

CA $107

CA $125 total

includes taxes & fees

Jan 12 - Jan 13

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

![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.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)

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

(3004)

"Great place to stay"

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

Elisha

CA $112

CA $132 total

includes taxes & fees

Jan 7 - Jan 8

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

![Exterior](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/160ef77b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/ab59d7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 2 Double Beds | Bathroom](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/bc30a848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/8c467470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sports Illustrated Resorts Chicago

[](https://www.expedia.ca/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.Hotel-Information)

Theatre District, 12.5 km from Sleepy Hollow

9.2/10

Wonderful

(1412)

"Staff was wonderful."

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

Jamie

CA $123

CA $183 total

includes taxes & fees

Jan 6 - Jan 7

[](https://www.expedia.ca/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.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=2026-01-17&endDate=2026-01-18&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
- Theatre District

![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 rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago which includes skyline, cbd and landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23710-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago featuring theatre scenes, a city and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23730-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Frank Lloyd Wright Home and Studio which includes interior views and a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26627-Frank-Lloyd-Wright-Home-And-Studio.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago featuring night scenes, rides and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23718-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=651190586167894016)

![Theatre District map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:mxs%7EF%7E%7EzuOa%40wb%40mAwCKcDmHiMl%7B%40MZry%40_o%40v%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wPQBnQtd4sat1wXcy-Q0SbgXS1s=)

### Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line). 

[See properties](https://www.expedia.ca/Hotel-Search?regionId=651190586167894016)

## Top Sleepy Hollow Hotel Reviews

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"Nice pillows"

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

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Dolores was incredible and our room was gorgeous! "

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

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

### River Hotel

10/10 Excellent

"I was there for the new years celebrations downtown. The hotel was very clean and organized. The security was also very attentive. They were checking people at the door and making sure that only registered guest came in which made me feel at ease, and at night the noice control was super quiet. For that festive occasion it was very controlled. "

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

"The view really makes this hotel worth it! The bench in my room was a bit worn but other than that nice hotel and great stay "

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

![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg)

### InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"The room was spacious with a great view. The bathroom was also plenty bug. 4 of us stayed comfortably for the night. The fitness center is great, if a bit warm, and the pool is excellent. Location is also perfect."

[](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.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 view of downtown Chicago, easy access to the Mart, and friendly/helpful staff "

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

![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg)

### Silversmith Hotel Chicago Downtown

10/10 Excellent

"."

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

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Staff was great, clean, nice bed"

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"Wonderful breakfast. Friendly and professionally competent staff!"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.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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