Hotels in Sleepy Hollow
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Our top choices for Sleepy Hollow hotels
1. Carleton of Oak Park
Carleton of Oak Park9.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,153 reviews)
"Fantastic stay"
Alan
The price is S$158
includes taxes & fees
14 Oct - 15 Oct
2. 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, (2,631 reviews)
"It is a great location with nice rooms"
Phillip
The price is S$247
includes taxes & fees
20 Sept - 21 Sept
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, (2,740 reviews)
"Very good hotel"
Diego
The price is S$270
includes taxes & fees
29 Sept - 30 Sept
4. Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,191 reviews)
"Enjoyable stay and a delicious breakfast."
Lori
The price is S$373
includes taxes & fees
25 Sept - 26 Sept
5. 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, (1,217 reviews)
"Excellent Stay. Staff were wonderful and welcoming."
Jennifer
The price is S$295
includes taxes & fees
20 Sept - 21 Sept
6. Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,231 reviews)
"Good place to stay location is amazing can’t get any better"
Manuel
The price is S$234
includes taxes & fees
27 Sept - 28 Sept
7. LIVN - West Loop Chicago
LIVN - West Loop Chicago10.9 km from Sleepy Hollow
9.2 out of 10, Wonderful, (259 reviews)
"It was a very nice place to stay"
chidubem
The price is S$222
includes taxes & fees
20 Sept - 21 Sept
8. 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, (1,006 reviews)
"Great stay right in the Loop and convenient to the L."
Scott
The price is S$240
includes taxes & fees
27 Sept - 28 Sept
9. The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 13.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,229 reviews)
"Loved this hotel, great location and wonderful accommodations, just perfect"
Laura
The price is S$242
includes taxes & fees
28 Sept - 29 Sept
10. Central Loop Hotel
Central Loop HotelTheatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,290 reviews)
"Great location."
Yiyang
The price is S$246
includes taxes & fees
20 Sept - 21 Sept
11. Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoThe Loop, 11.8 km from Sleepy Hollow
7.6 out of 10, Good, (2,839 reviews)
"Clean quiet room good location"
Durant
The price is S$229
includes taxes & fees
27 Sept - 28 Sept
12. La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago DowntownThe Loop, 11.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,908 reviews)
"Our stay was great."
Mythli
The price is S$319
includes taxes & fees
20 Sept - 21 Sept
13. River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,436 reviews)
"Excellent stay!!"
steve
The price is S$229
includes taxes & fees
27 Sept - 28 Sept
14. Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,393 reviews)
"Loved our stay at this hotel"
Zamira
The price is S$314
includes taxes & fees
21 Sept - 22 Sept
15. 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, (1,596 reviews)
"Great place to stay!"
LISA
The price is S$331
includes taxes & fees
20 Sept - 21 Sept
16. 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, (2,687 reviews)
"Amazing place to stay"
Shanequa
The price is S$480
includes taxes & fees
27 Sept - 28 Sept
17. citizenM Chicago Downtown
citizenM Chicago DowntownTheatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,347 reviews)
"Had a great stay, would definitely book here again!"
Isayra
The price is S$291
includes taxes & fees
20 Sept - 21 Sept
18. Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,355 reviews)
"Super convenient location and very helpful and friendly staff."
Jacqueline
The price is S$286
includes taxes & fees
20 Sept - 21 Sept
19. Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 11.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"This hotel was perfect. Room was a great size, clean, very friendly staff. Perfect for our work trip!"
amanda
The price is S$353
includes taxes & fees
20 Sept - 21 Sept
20. Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, ChicagoTheatre District, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (3,643 reviews)
"Clean hotel and friendly staff"
Jacqueline
The price is S$280
includes taxes & fees
27 Sept - 28 Sept
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.
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas 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
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
