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Our top choices for Sleepy Hollow hotels

1. Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton Market10.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,308 reviews)
The price is CA $208
CA $248 total
includes taxes & fees
Nov 22 - Nov 23

2. Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,526 reviews)
The price is CA $151
CA $220 total
includes taxes & fees
Nov 27 - Nov 28

3. Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,737 reviews)
The price is CA $119
CA $142 total
includes taxes & fees
Dec 7 - Dec 8

4. Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopThe Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,195 reviews)
The price is CA $135
CA $159 total
includes taxes & fees
Nov 23 - Nov 24

5. Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South LoopThe Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,530 reviews)
The price is CA $147
CA $173 total
includes taxes & fees
Nov 23 - Nov 24

6. Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHGWest Loop, 10.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,269 reviews)
The price is CA $141
CA $185 total
includes taxes & fees
Nov 23 - Nov 24

7. Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonStreeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,765 reviews)
The price is CA $183
CA $266 total
includes taxes & fees
Nov 23 - Nov 24

8. Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,789 reviews)
The price is CA $161
CA $191 total
includes taxes & fees
Nov 22 - Nov 23

9. Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 11.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,000 reviews)
The price is CA $157
CA $211 total
includes taxes & fees
Dec 7 - Dec 8

10. Hotel Chicago Downtown, Autograph Collection by Marriott
Hotel Chicago Downtown, Autograph Collection by MarriottRiver North, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
The price is CA $108
CA $170 total
includes taxes & fees
Nov 22 - Nov 23

11. Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The LoopThe Loop, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,692 reviews)
The price is CA $165
CA $196 total
includes taxes & fees
Nov 23 - Nov 24

12. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,577 reviews)
The price is CA $135
CA $161 total
includes taxes & fees
Dec 7 - Dec 8

13. Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre DistrictTheatre District, 12 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,002 reviews)
The price is CA $159
CA $189 total
includes taxes & fees
Nov 23 - Nov 24

14. Cambria Hotel Chicago Loop - Theatre District
Cambria Hotel Chicago Loop - Theatre DistrictTheatre District, 12.2 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,712 reviews)
The price is CA $149
CA $177 total
includes taxes & fees
Nov 23 - Nov 24

15. LIVN - West Loop Chicago
LIVN - West Loop Chicago10.9 km from Sleepy Hollow
9.2 out of 10, Wonderful, (397 reviews)
The price is CA $140
CA $164 total
includes taxes & fees
Nov 8 - Nov 9

16. Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,103 reviews)
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23

17. Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by Hilton13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,432 reviews)
The price is CA $124
CA $188 total
includes taxes & fees
Nov 22 - Nov 23

18. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio HotelTheatre District, 11.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,003 reviews)
The price is CA $166
CA $198 total
includes taxes & fees
Dec 3 - Dec 4

19. Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoThe Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,217 reviews)
The price is CA $195
CA $231 total
includes taxes & fees
Dec 6 - Dec 7

20. citizenM Chicago Downtown
citizenM Chicago DowntownTheatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,361 reviews)
The price is CA $162
CA $193 total
includes taxes & fees
Nov 23 - Nov 24
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.
Compare top hotels in Sleepy Hollow
![]() Hyatt House Chicago/West Loop-Fulton Market10.6 km from Sleepy Hollow | ![]() Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow | ![]() Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow | ![]() Hilton Garden Inn Chicago Downtown South LoopThe Loop, 11.4 km from Sleepy Hollow | ![]() Homewood Suites by Hilton Chicago Downtown South LoopThe Loop, 11.4 km from Sleepy Hollow |
|---|---|---|---|---|
9.0 Wonderful 1,308 reviews | 8.6 Excellent 3,526 reviews | 8.2 Very good 2,737 reviews | 8.8 Excellent 2,195 reviews | 8.8 Excellent 2,530 reviews |
The price is CA $208 CA $248 total includes taxes & fees Nov 22 - Nov 23 | The price is CA $151 CA $220 total includes taxes & fees Nov 27 - Nov 28 | The price is CA $119 CA $142 total includes taxes & fees Dec 7 - Dec 8 | The price is CA $135 CA $159 total includes taxes & fees Nov 23 - Nov 24 | The price is CA $147 CA $173 total includes taxes & fees Nov 23 - Nov 24 |
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Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.

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.

Photo by © City of Chicago
Open Photo by © City of Chicago
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.

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.

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.

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

Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton MarketDowntown Chicago








































































































