- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
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 $162
CA $193 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. 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, (2,194 reviews)
The price is CA $135
CA $161 total
includes taxes & fees
Nov 23 - Nov 24

4. Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,736 reviews)
The price is CA $125
CA $148 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 $175 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, (1,268 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 $189
CA $225 total
includes taxes & fees
Nov 23 - Nov 24

9. 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, (1,691 reviews)
The price is CA $165
CA $196 total
includes taxes & fees
Nov 23 - Nov 24

10. 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

11. 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

12. 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 $166
CA $223 total
includes taxes & fees
Nov 26 - Nov 27

13. Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central LoopThe Loop, 11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,442 reviews)
The price is CA $189
CA $225 total
includes taxes & fees
Nov 22 - Nov 23

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. 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

16. 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, (1,957 reviews)
The price is CA $126
CA $150 total
includes taxes & fees
Dec 6 - Dec 7

17. Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,102 reviews)
The price is CA $162
CA $193 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, (1,002 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, (1,216 reviews)
The price is CA $224
CA $266 total
includes taxes & fees
Nov 22 - Nov 23

20. 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 $141
CA $168 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 | ![]() Hilton Garden Inn Chicago Downtown South LoopThe Loop, 11.4 km from Sleepy Hollow | ![]() Best Western Grant Park HotelThe Loop, 11.5 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 | 8.8 Excellent 2,194 reviews | 8.2 Very good 2,736 reviews | 8.8 Excellent 2,530 reviews |
The price is CA $162 CA $193 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 $135 CA $161 total includes taxes & fees Nov 23 - Nov 24 | The price is CA $125 CA $148 total includes taxes & fees Nov 23 - Nov 24 | The price is CA $147 CA $175 total includes taxes & fees Nov 23 - Nov 24 |
|
|
|
|
|
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








































































































