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Our top choices for Sleepy Hollow hotels

1. Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,742 reviews)
The price is CA $121
CA $144 total
includes taxes & fees
Dec 7 - Dec 8

2. Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,530 reviews)
The price is CA $153
CA $223 total
includes taxes & fees
Nov 27 - Nov 28

3. 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, (1,311 reviews)
The price is CA $211
CA $250 total
includes taxes & fees
Nov 22 - Nov 23

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, (2,196 reviews)
The price is CA $135
CA $161 total
includes taxes & fees
Dec 9 - Dec 10

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, (2,534 reviews)
The price is CA $149
CA $175 total
includes taxes & fees
Nov 23 - Nov 24

6. 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 $158
CA $213 total
includes taxes & fees
Dec 7 - Dec 8

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, (2,773 reviews)
The price is CA $185
CA $269 total
includes taxes & fees
Nov 23 - Nov 24

8. 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, (1,272 reviews)
The price is CA $143
CA $187 total
includes taxes & fees
Nov 23 - Nov 24

9. 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, (1,221 reviews)
The price is CA $197
CA $234 total
includes taxes & fees
Dec 6 - Dec 7

10. 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, (2,804 reviews)
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23

11. Best Western River North Hotel
Best Western River North HotelRiver North, 12.6 km from Sleepy Hollow
7.8 out of 10, Good, (1,191 reviews)
The price is CA $113
CA $134 total
includes taxes & fees
Dec 7 - Dec 8

12. ACME Hotel Chicago, Outset Collection by Hilton
ACME Hotel Chicago, Outset Collection by HiltonRiver North, 12.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,958 reviews)
The price is CA $120
CA $142 total
includes taxes & fees
Dec 7 - Dec 8

13. 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, (1,701 reviews)
The price is CA $167
CA $198 total
includes taxes & fees
Nov 23 - Nov 24

14. LIVN - West Loop Chicago
LIVN - West Loop Chicago10.9 km from Sleepy Hollow
9.2 out of 10, Wonderful, (402 reviews)
The price is CA $146
CA $171 total
includes taxes & fees
Nov 11 - Nov 12

15. 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 $161
CA $191 total
includes taxes & fees
Nov 23 - Nov 24

16. 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, (1,715 reviews)
The price is CA $150
CA $179 total
includes taxes & fees
Nov 23 - Nov 24

17. The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier CollectionStreeterville, 13.5 km from Sleepy Hollow
8.4 out of 10, Very good, (3,967 reviews)
The price is CA $114
CA $136 total
includes taxes & fees
Dec 7 - Dec 8

18. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,582 reviews)
The price is CA $137
CA $163 total
includes taxes & fees
Dec 7 - Dec 8

19. citizenM Chicago Downtown
citizenM Chicago DowntownTheatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,370 reviews)
The price is CA $164
CA $195 total
includes taxes & fees
Nov 23 - Nov 24

20. La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago DowntownThe Loop, 11.6 km from Sleepy Hollow
8.4 out of 10, Very good, (2,948 reviews)
The price is CA $161
CA $217 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
![]() Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow | ![]() Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow | ![]() Hyatt House Chicago/West Loop-Fulton Market10.6 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 |
|---|---|---|---|---|
8.2 Very good 2,742 reviews | 8.6 Excellent 3,530 reviews | 9.0 Wonderful 1,311 reviews | 8.8 Excellent 2,196 reviews | 8.8 Excellent 2,534 reviews |
The price is CA $121 CA $144 total includes taxes & fees Dec 7 - Dec 8 | The price is CA $153 CA $223 total includes taxes & fees Nov 27 - Nov 28 | The price is CA $211 CA $250 total includes taxes & fees Nov 22 - Nov 23 | The price is CA $135 CA $161 total includes taxes & fees Dec 9 - Dec 10 | The price is CA $149 CA $175 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

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








































































































