Search Hotels in Sleepy Hollow, Chicago
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
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, (2,382 reviews)
"Great stay"
Blake
The price is ฿4,488
฿6,325 total
includes taxes & fees
30 Mar - 31 Mar
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,070 reviews)
"Great place "
Kamilah
The price is ฿5,251
฿7,258 total
includes taxes & fees
24 Mar - 25 Mar
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,434 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
Brisa
The price is ฿3,507
฿4,992 total
includes taxes & fees
4 Mar - 5 Mar
Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,657 reviews)
"Yes it was a great stay"
Rita
The price is ฿4,048
฿5,663 total
includes taxes & fees
1 Apr - 2 Apr
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (9,903 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
Jennifer
The price is ฿5,365
฿6,298 total
includes taxes & fees
27 Mar - 28 Mar
Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,115 reviews)
"Great location and friendly staff. "
Pablo
The price is ฿2,670
฿3,134 total
includes taxes & fees
5 Mar - 6 Mar
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,015 reviews)
"Location was great, staff was very friendly, and the rooms were clean. "
Lori
The price is ฿3,791
฿5,359 total
includes taxes & fees
18 Mar - 19 Mar
Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,203 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
Jon
The price is ฿3,776
฿5,526 total
includes taxes & fees
29 Mar - 30 Mar
Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,000 reviews)
"Clean hotel, helpful staff, restaurant food was delicious, great atmosphere, fabulous location!"
Jennifer
The price is ฿3,604
฿5,157 total
includes taxes & fees
25 Mar - 26 Mar
The Blackstone, Autograph Collection
The Blackstone, Autograph CollectionThe Loop, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful place to stay, nice staff 🙏"
Yu Ching Dexter
The price is ฿4,335
฿6,000 total
includes taxes & fees
5 Mar - 6 Mar
Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 11.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,002 reviews)
"Great place to stay..awesome staff!"
Veronica
The price is ฿2,920
฿3,974 total
includes taxes & fees
3 Mar - 4 Mar
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, (1,872 reviews)
"Absolutely enjoyed my time here"
Quayshaun
The price is ฿3,399
฿3,990 total
includes taxes & fees
5 Mar - 6 Mar
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,311 reviews)
"Excellent stay, we loved it "
Melani
The price is ฿4,099
฿5,587 total
includes taxes & fees
1 Apr - 2 Apr
L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (3,711 reviews)
"Great location and overall great hotel."
Fernando
The price is ฿4,250
฿4,989 total
includes taxes & fees
17 Mar - 18 Mar
Hyatt Centric The Loop Chicago
Hyatt Centric The Loop ChicagoTheatre District, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,389 reviews)
"Super comfy beds, helpful staff, free coffee and snacks and an amazing location "
Stephanie
The price is ฿4,097
฿4,809 total
includes taxes & fees
6 Mar - 7 Mar
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,467 reviews)
"Clean room, great staff, great location "
Tiffany
The price is ฿5,060
฿7,034 total
includes taxes & fees
1 Apr - 2 Apr
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very good, (1,294 reviews)
"Great hotel with great location. Would definitely stay here again. "
Sheila
The price is ฿3,317
฿3,894 total
includes taxes & fees
3 Mar - 4 Mar
Eurostars Magnificent Mile
Eurostars Magnificent MileRiver North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,278 reviews)
"Great stay "
Kylee
The price is ฿3,477
฿4,082 total
includes taxes & fees
3 Mar - 4 Mar
River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,030 reviews)
"Great stay, good location, accommodating staff."
Ian
The price is ฿3,140
฿3,686 total
includes taxes & fees
3 Mar - 4 Mar
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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.
O'Hare
Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.
Top Sleepy Hollow Hotel Reviews
LondonHouse Chicago, Curio Collection by Hilton
10/10 Excellent
