Find 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
Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by HiltonGold Coast, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,517 reviews)
"Great location, friendly staff and nice room"
Srinivasa
The price is NT$1,782
NT$3,017 total
includes taxes & fees
Feb 9 - Feb 10
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, (2,349 reviews)
"Great stay"
Blake
The price is NT$3,320
NT$4,970 total
includes taxes & fees
Feb 3 - Feb 4
Thompson Chicago, by Hyatt
Thompson Chicago, by HyattGold Coast, 13.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,318 reviews)
"Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. "
Yoshio
The price is NT$4,473
NT$6,180 total
includes taxes & fees
Feb 13 - Feb 14
Moxy Chicago Downtown
Moxy Chicago DowntownRiver North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (876 reviews)
"Great hotel, lots of fun and great location! "
Amber
The price is NT$3,402
NT$3,993 total
includes taxes & fees
Feb 8 - Feb 9
Level Chicago Fulton Market
Level Chicago Fulton MarketWest Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (393 reviews)
"The hotel in it’s entirety was better than advertised "
Eric
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,321 reviews)
"The rooms are beautiful and the staff is wonderful."
Melissa
The price is NT$5,328
NT$7,179 total
includes taxes & fees
Jan 28 - Jan 29
The Hoxton Chicago
The Hoxton Chicago11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,007 reviews)
"Amazing, I loved my stay"
Valerie
Springhill Suites by Marriott Chicago Downtown/ River North
Springhill Suites by Marriott Chicago Downtown/ River NorthRiver North, 12.6 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,032 reviews)
" Clean rooms
Hot shower great after a freezing cold day
Staff all polite and helpful
Great location "
John
The price is NT$3,622
NT$4,252 total
includes taxes & fees
Feb 1 - Feb 2
Hampton Inn Chicago West Loop Fulton Market Area
Hampton Inn Chicago West Loop Fulton Market Area11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice hotel and staff.
"
Wendy
The price is NT$3,989
NT$4,683 total
includes taxes & fees
Feb 6 - Feb 7
citizenM Chicago Downtown
citizenM Chicago DowntownTheatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,210 reviews)
"Very nice Hotel, great atmosphere friendly staff. I had a great stay!"
Lucie Saint Jean
The price is NT$3,244
NT$3,809 total
includes taxes & fees
Feb 1 - Feb 2
Hyatt House Chicago West Loop
Hyatt House Chicago West Loop10.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,179 reviews)
"Staff is wonderful, nice clean rooms, centrally located, loved staying here. "
Cassandra
The price is NT$4,536
NT$5,325 total
includes taxes & fees
Feb 5 - Feb 6
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,564 reviews)
"Clean accommodations and friendly staff."
usha
The price is NT$4,365
NT$5,124 total
includes taxes & fees
Feb 22 - Feb 23
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, (1,280 reviews)
"Great hotel at an affordable price "
Dhruv
The price is NT$3,619
NT$4,249 total
includes taxes & fees
Jan 28 - Jan 29
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent MileRiver North, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (4,359 reviews)
"All things about this hotel was good from the location to the staff"
Cisco
The price is NT$2,686
NT$3,153 total
includes taxes & fees
Feb 3 - Feb 4
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,848 reviews)
"Excellent front desk, rooms, pool/whirlpool and especially gym. "
Victoria Lynn Davis
The price is NT$4,962
NT$6,644 total
includes taxes & fees
Feb 15 - Feb 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, (1,945 reviews)
"Very convenient place to stay friendly and helpful staff."
Rick
The price is NT$2,299
NT$2,699 total
includes taxes & fees
Feb 3 - Feb 4
The Emily Hotel
The Emily Hotel11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,304 reviews)
"Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again. "
Mary
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,268 reviews)
"amazing stay"
Anani
The price is NT$2,686
NT$3,153 total
includes taxes & fees
Feb 3 - Feb 4
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,828 reviews)
"Great hotel staff and location. "
Jacqueline
The price is NT$3,359
NT$4,868 total
includes taxes & fees
Feb 3 - Feb 4
Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,067 reviews)
"All around a nice stay for the holiday "
Alec
The price is NT$2,646
NT$3,106 total
includes taxes & fees
Feb 3 - Feb 4
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 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.
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.
O'Hare
Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.
Top Sleepy Hollow Hotel Reviews
LondonHouse Chicago, Curio Collection by Hilton
10/10 Excellent
Frequently asked questions
Explore a world of travel with Expedia
- Cicero Hotels
- Hotels near 54th-Cermak Station
- Hotels near Berwyn Harlem Avenue Station
- Hotels near Old St Patrick’s Church
- Hotels near Chicago Union Station
- Oak Park Hotels
- Hotels near Illinois Medical District Station
- Forest Park Hotels
- Cheap Hotels in Garfield Ridge
- La Grange Hotels
- Burbank Hotels
- Hotels near Midway Intl.
- Englewood Hotels
- Hotels near Wintrust Arena
- Hotels near Chicago Ridge Shopping Mall
- Pilsen Hotels
- Hotels near Monadnock Building
- Hotels near Ashland-63rd Station
- Fulton Market Hotels
- Hotels near Berwyn Station
- Hyatt Hotels in Clearing
- Hotels near Oak Park Conservatory
- Hotels near Halsted Station
- Hotels near Oak Park Station
- Hotels near Chicago Western Avenue Station
- Hotels near Chicago Wrightwood Station
- Hostmark Hospitality Group Hotels in Garfield Manor
- Hotels near Bridgeport Art Center
- Douglas Park Hotels
- Hotels near Chicago 35th Street-Lou Jones-Bronzeville Station
- Hotels near Chicago Halsted Station
- Hotels near Unity Temple
- Hometown Hotels
- Flights from Drake Bay (DRK) to Chicago (MDW)
- Flights from San Francisco (SFO) to Chicago (MDW)
- Flights from Kissimmee (ISM) to Chicago (MDW)
- Flights from Osaka (KIX) to Chicago (MDW)
- Flights from Boston (BOS) to Chicago (MDW)
- Flights from Boca Raton (BCT) to Chicago (MDW)
- Flights from Ontario (ONT) to Chicago (MDW)
- Flights from Kano (KAN) to Chicago (MDW)
- Flights from Houston (HOU) to Chicago (MDW)
- Flights from Green Bay (GRB) to Chicago (MDW)
- Flights from Philadelphia (PHL) to Chicago (MDW)
- Flights from Billings (BIL) to Chicago (MDW)
- Flights from Houston (IAH) to Chicago (MDW)
- Flights from Ogdensburg (OGS) to Chicago (MDW)
- Flights from Baotou (BAV) to Chicago (MDW)
- Flights from Indianapolis (IND) to Chicago (MDW)
- Flights from Allentown (ABE) to Chicago (MDW)
- Flights from Sioux Falls (FSD) to Chicago (MDW)
- Flights from Natal (NAT) to Chicago (MDW)
- Flights from Geneva (GVA) to Chicago (MDW)
- Flights from Borroloola (BOX) to Chicago (MDW)
- Flights from Rangiroa (RGI) to Chicago (MDW)
- Flights from Cootamundra (CMD) to Chicago (MDW)
- Flights from Nashville (BNA) to Chicago (MDW)
- Flights from Warsaw (WAW) to Chicago (MDW)
- Flights from Québec (YQB) to Chicago (MDW)
- Flights from Bowling Green (BWG) to Chicago (MDW)
- Flights from Eagle Pass (EGP) to Chicago (MDW)
- Flights from Sacramento (SMF) to Chicago (MDW)
- Flights from Paris (PAR) to Chicago (MDW)
- Flights from Fort Walton Beach (VPS) to Chicago (MDW)
- Flights from Taipei (TPE) to Chicago (MDW)
- Flights from Rhinelander (RHI) to Chicago (MDW)
- Flights from Çukurova Intl. Airport (COV) to Chicago (MDW)
- Flights from Augusta (AGS) to Chicago (MDW)
- Flights from Calabar (CBQ) to Chicago (MDW)
- Flights from Midway Intl.
- Flights from Baltimore (BWI) to Chicago (MDW)
- Flights from Washington (DCA) to Chicago (MDW)
- Flights from Fargo (FAR) to Chicago (MDW)
- Flights from Emporia (EMP) to Chicago (MDW)
- Flights from Greensboro (GSO) to Chicago (MDW)
- Flights from St. Louis (STL) to Chicago (MDW)
- Flights from Tampa (TPA) to Chicago (MDW)
- Flights from El Paso (ELP) to Chicago (MDW)
- Flights from Columbia (COU) to Chicago (MDW)
- Flights from Laughlin (IFP) to Chicago (MDW)
- Flights from Las Vegas (LAS) to Chicago (MDW)
- Flights from Waterford (WAT) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from Salekhard (SLY) to Chicago (MDW)
- Flights from Orange County (SNA) to Chicago (MDW)
- Flights from Cascavel (CAC) to Chicago (MDW)
- Flights from Bloomington (BMI) to Chicago (MDW)
- Flights from Denver (APA) to Chicago (MDW)
- Flights from New Bern (EWN) to Chicago (MDW)
- Flights from Tokyo (NRT) to Chicago (MDW)