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
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, (2,514 reviews)
"I loved it here and will definitely stay again."
Gina
The price is NT$7,885
NT$10,463 total
includes taxes & fees
Jun 14 - Jun 15
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,638 reviews)
"Beautiful views"
Dominique
The price is NT$10,381
NT$13,468 total
includes taxes & fees
Jun 14 - Jun 15
Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,347 reviews)
"Great location!"
Maria
The price is NT$6,735
NT$9,118 total
includes taxes & fees
Jun 14 - Jun 15
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,488 reviews)
"This is a beautiful hotel and the location was perfect."
Felisha
The price is NT$6,229
NT$7,406 total
includes taxes & fees
May 27 - May 28
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, (2,856 reviews)
"Breakfast was excellent."
Janine
The price is NT$5,333
NT$7,266 total
includes taxes & fees
May 27 - May 28
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,945 reviews)
"Great Hotel "
Dylan
The price is NT$8,025
NT$10,516 total
includes taxes & fees
Jun 14 - Jun 15
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,169 reviews)
"Great place"
JOSE
The price is NT$7,003
NT$9,448 total
includes taxes & fees
May 27 - May 28
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,251 reviews)
"Nice place to stay"
Jimmie
The price is NT$7,078
NT$8,416 total
includes taxes & fees
Jun 14 - Jun 15
Ivy Boutique Hotel
Ivy Boutique HotelStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,274 reviews)
"Happy with our stay!"
Jennifer
The price is NT$6,102
NT$7,163 total
includes taxes & fees
Jun 17 - Jun 18
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Sonesta ES Suites Chicago Downtown Magnificent Mile - MedicalStreeterville, 13.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,481 reviews)
"Perfect location, very comfortable rooms, friendly staff."
Annabelle
The price is NT$5,637
NT$6,702 total
includes taxes & fees
May 27 - May 28
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Fairfield Inn & Suites Chicago Downtown / Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"All around great stay. "
Nicholas
The price is NT$5,017
NT$5,965 total
includes taxes & fees
May 27 - May 28
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,344 reviews)
"Beautiful Hotel great location"
Nereida
The price is NT$5,946
NT$7,069 total
includes taxes & fees
May 27 - May 28
Millennium Hotel Knickerbocker Chicago
Millennium Hotel Knickerbocker ChicagoStreeterville, 13.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,979 reviews)
"Loved everything including location and food options. Great hotel. "
Eileen
The price is NT$4,544
NT$6,152 total
includes taxes & fees
May 27 - May 28
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,499 reviews)
"Very good place to stay. I really liked the lobby — it’s very spacious. The lobby design is also very open and artistic."
Tong
The price is NT$9,308
NT$12,192 total
includes taxes & fees
May 27 - May 28
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,096 reviews)
"Great stay!"
Milo
The price is NT$8,109
NT$10,579 total
includes taxes & fees
Jun 17 - Jun 18
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,908 reviews)
"Great Place to stay while in Chicago."
Stacy
The price is NT$6,784
NT$8,168 total
includes taxes & fees
Jun 14 - Jun 15
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent MileStreeterville, 13.5 km from Sleepy Hollow
7.8 out of 10, Good, (1,476 reviews)
"Great stay"
Ontario
The price is NT$6,002
NT$7,136 total
includes taxes & fees
Jun 3 - Jun 4
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,248 reviews)
"Great location & breakfast was amazing."
sierra
The price is NT$7,519
NT$9,836 total
includes taxes & fees
Jun 16 - Jun 17
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (10,141 reviews)
"Excellent stay"
Jennifer
The price is NT$4,214
NT$5,010 total
includes taxes & fees
May 27 - May 28
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.
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
Club Quarters Hotel, Central Loop, Chicago
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)