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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## 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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&amenities=PETS)

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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&amenities=WATER_PARK)

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=2025-12-29&d1=2025-12-29&endDate=2025-12-31&d2=2025-12-31&lodging=CONDO)

## Check prices for these dates

Tonight

[Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-12-26&endDate=2025-12-28&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)

![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)

![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)

![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

(1485)

"I really liked this location - we will stay here again. "

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

Lynnsey

CA $95

CA $152 total

includes taxes & fees

Dec 22 - Dec 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)

![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a68260d2.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

(2263)

"Great staff and restaurants!!"

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

Abigale

CA $126

CA $195 total

includes taxes & fees

Dec 23 - Dec 24

[](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/w2557h3837x3y3-5ce449d4.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)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/8b216cef.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

(1296)

"Great hotel!"

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

Julie

CA $186

CA $259 total

includes taxes & fees

Dec 28 - Dec 29

[](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)

![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)

![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)

### 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

(853)

"Great place to stay"

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

Mason

CA $155

CA $182 total

includes taxes & fees

Dec 21 - Dec 22

[](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)

![Executive lounge](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364.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

(358)

"Great hotel!"

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

Giselle

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

![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/0f7d6f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/dbdc843c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/4dbc75df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/7c1b873a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

[](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-West-Loop.h15816026.Hotel-Information)

11.4 km from Sleepy Hollow

9.2/10

Wonderful

(1003)

"Good place to stay in."

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

Joan

CA $175

CA $206 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-West-Loop.h15816026.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)

![Lobby](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/9752c1a4.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)

![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)

### The Hoxton Chicago

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

Fulton Market, 11 km from Sleepy Hollow

9.0/10

Wonderful

(1005)

"Awesome hotel"

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

Eligija

[](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)

![Reception](https://images.trvl-media.com/lodging/2000000/1770000/1760900/1760845/308aeba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/2000000/1770000/1760900/1760845/736cfc64.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

9.2/10

Wonderful

(1004)

"We enjoyed the staying for the location "

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

CARLOS ALBERTO

CA $165

CA $194 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/1c60a07e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Suite, 1 Bedroom](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/d0d24426.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)

### 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

(2265)

"Lovely hotel! Exceptionally clean and affordable!"

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

Robin

CA $222

CA $301 total

includes taxes & fees

Dec 17 - Dec 18

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

![Exterior](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/7b541fe1.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)

![Meeting facility](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/10a353c8.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

(1002)

"Good service & nice clean rooms "

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

Yessica

CA $164

CA $193 total

includes taxes & fees

Dec 26 - Dec 27

[](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

(4112)

"Great stay"

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

Ericka

CA $142

CA $167 total

includes taxes & fees

Dec 21 - Dec 22

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

![2 bars/lounges, rooftop bar, cocktail bar](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/e039fcfe.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)

### 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

(3437)

"Loved the location and view!"

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

Erica

CA $180

CA $211 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

![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)

![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/w2880h1919x0y0-235561ea.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

(1786)

"Friendly staff and good location to all of the city"

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

Mark

CA $193

CA $262 total

includes taxes & fees

Dec 28 - Dec 29

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

![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)

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

8.4/10

Very good

(4245)

"Excellent location Restaurant attached "

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

Rebecca

CA $115

CA $135 total

includes taxes & fees

Dec 21 - Dec 22

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

![Sports facility](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/f4944277.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)

### 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

(1259)

"Solid stay in a great part of town"

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

Michael

CA $166

CA $195 total

includes taxes & fees

Jan 9 - Jan 10, 2026

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

![Fitness facility](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/1d01cf8c.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)

Fulton Market, 10.6 km from Sleepy Hollow

8.8/10

Excellent

(1129)

"I always come back to this Hotel everything is close the area is full of things to do really love staying here !!"

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

Sandra

CA $186

CA $218 total

includes taxes & fees

Dec 28 - Dec 29

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

![Lobby](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/357f9e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/2ee04c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/5a6cccaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pillowtop beds, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/30b0cabc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Fairfield-Inn-Suites-Chicago-Downtown-Magnificent-Mile.h571328.Hotel-Information)

Streeterville, 13.3 km from Sleepy Hollow

9.0/10

Wonderful

(1003)

"Great ubicación and great breakfast "

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

Andrea

CA $105

CA $123 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chicago-Hotels-Fairfield-Inn-Suites-Chicago-Downtown-Magnificent-Mile.h571328.Hotel-Information)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4a14c915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/311c65a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/066ab9a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sheraton Grand Chicago Riverwalk

[](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.Hotel-Information)

Streeterville, 13.2 km from Sleepy Hollow

8.4/10

Very good

(1580)

"Rooms were very nice and staff was great"

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

Nancy

CA $205

CA $282 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.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/20000000/19390000/19381200/19381112/37ee31ac.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)

![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)

### The Emily Hotel

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

Fulton Market, 11.1 km from Sleepy Hollow

9.2/10

Wonderful

(1282)

"Very pleasant stay for my birthday! Will definitely come back and recommend to others! Top notch service and rooms were beautiful and comfortable!"

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

Daniela

CA $239

CA $281 total

includes taxes & fees

Dec 27 - Dec 28

[](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)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.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)

### 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

(2197)

"Yes, very clean room and great hospitality "

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

leticia i Vasquez

CA $123

CA $144 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.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=2025-12-29&endDate=2025-12-30&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

![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

"The room was very spacious, the hotel lobby and bar are beautiful. Staff is super friendly and helpful! Would definitely stay here again"

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

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

### Eurostars Magnificent Mile

10/10 Excellent

"Loved the location and the room was nice with a view!"

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

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

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Hotel was very nice. Clean and quiet rooms. Good value for the price. Staff was super friendly and overly accommodating during our stay. From the curb service upon arrival, the maintenance man that had to make a minor repair in our room to the bellman that waited at the curb with us to load our bags in the uber. Cannot recommend this hotel enough!"

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

"Beautiful old hotel convenient to downtown . Wonderful rooms and great onsite dining. You can hear the trains outside from pretty much every room but I found it acceptable noise level. "

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

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"Great hotel "

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

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

### River Hotel

10/10 Excellent

"The staff was amazing and our room was just as good. Can’t wait to come back!"

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

"The room view was beautiful! The staff was super attentive and helpful. "

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

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

### Hilton Chicago

10/10 Excellent

"Everything was wonderful. We did not have breakfast"

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

![Homewood Suites by Hilton Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/2d5c8626_y.jpg)

### Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent

"Cleanliness of the room "

[](https://expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.Hotel-Information)

## Frequently asked questions

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

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

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

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