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Find hotels in Woodlawn, Chicago from ￥13,902

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Our top choices for Woodlawn hotels

Hallway
Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.4 out of 10, (48)
"Clean room "
United States
Pierre
The price is ￥13,400
￥16,821 total
includes taxes & fees
Dec 19 - Dec 20
Best Motel By OYO Chicago I-90
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 12.6 km from Woodlawn
9.4 out of 10, Exceptional, (2262)
"Great staff and restaurants!!"
United States
Abigale
The price is ￥14,437
￥22,253 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Premium bedding, down comforters, pillowtop beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very Good, (1519)
"Great staff and great location. "
United States
Joe
The price is ￥15,737
￥18,475 total
includes taxes & fees
Dec 18 - Dec 19
The Wade
Reception
Swissotel - Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3017)
"Very beautiful place to stay"
United States
FaithBrenda
The price is ￥17,759
￥25,420 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Swissotel - Chicago
Meeting facility
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.4 out of 10, Very Good, (1580)
"Rooms were very nice and staff was great"
United States
Nancy
The price is ￥23,216
￥31,928 total
includes taxes & fees
Dec 21 - Dec 22
Sheraton Grand Chicago Riverwalk
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 12.7 km from Woodlawn
8.4 out of 10, Very Good, (2746)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is ￥12,091
￥18,767 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2195)
"Yes, very clean room and great hospitality "
United States
leticia i Vasquez
The price is ￥13,926
￥16,348 total
includes taxes & fees
Dec 21 - Dec 22
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool, seasonal outdoor pool, free cabanas, sun loungers
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.2 km from Woodlawn
8.6 out of 10, Excellent, (1786)
"Friendly staff and good location to all of the city"
United States
Mark
The price is ￥21,801
￥29,643 total
includes taxes & fees
Dec 28 - Dec 29
Radisson Blu Aqua Hotel Chicago
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2963)
"Great location, the staff was friendly and the room was very clean. "
United States
Breanna
The price is ￥12,309
￥14,451 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Aloft Chicago Mag Mile
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.8 out of 10, Excellent, (1041)
"Staff was amazing! "
United States
Ahren
Ivy Boutique Hotel
Lobby
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 13.7 km from Woodlawn
8.6 out of 10, Excellent, (2291)
"Excellent hotel. Loved staying there"
United States
cristina
The price is ￥14,443
￥16,955 total
includes taxes & fees
Dec 21 - Dec 22
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Pillowtop beds, desk, blackout drapes, iron/ironing board
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Streeterville, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1003)
"Great ubicación and great breakfast "
United States
Andrea
The price is ￥11,842
￥13,902 total
includes taxes & fees
Dec 21 - Dec 22
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3399)
"I always love staying at this place when I visit"
Canada
William
The price is ￥21,190
￥29,447 total
includes taxes & fees
Dec 28 - Dec 29
Hyatt Regency Chicago
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.6 km from Woodlawn
9.0 out of 10, Wonderful, (3486)
"Great place to stay "
United States
RaShawna
The price is ￥12,649
￥14,847 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Chicago/Magnificent Mile Suites
Lobby
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Streeterville, 13.6 km from Woodlawn
8.6 out of 10, Excellent, (2006)
"Great location, clean hotel"
United States
Andre
The price is ￥13,867
￥19,936 total
includes taxes & fees
Dec 17 - Dec 18
Millennium Knickerbocker Chicago
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 13 km from Woodlawn
9.0 out of 10, Wonderful, (1053)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is ￥15,269
￥22,497 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hyatt Centric Chicago Magnificent Mile
Breakfast and lunch served
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1598)
"Great location and friendly staff. "
United States
Eric Lynn
The price is ￥15,230
￥17,877 total
includes taxes & fees
Dec 18 - Dec 19
Courtyard by Marriott Chicago Magnificent Mile
Exterior
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.2 km from Woodlawn
7.6 out of 10, Good, (1170)
"The room was spacious and clean and it was a good value."
United States
Dj
The Chicago Hotel Collection - Magnificent Mile
Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | View from room
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 13.1 km from Woodlawn
8.0 out of 10, Very Good, (1344)
"Very happy with my two stays here. "
United States
Courteney
The price is ￥13,586
￥15,950 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Chicago Downtown/Magnificent Mile
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (2978)
"Excellent stay great location and great rooms"
United States
Joseph
The price is ￥15,529
￥22,621 total
includes taxes & fees
Dec 21 - Dec 22
Hotel Riu Plaza Chicago
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.
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Where to stay in Woodlawn

Find the best Woodlawn areas and neighborhoods for the activities you enjoy most.
Downtown Chicago showing a city

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 - River North

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 - Downtown which includes a river or creek

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 showing railway items, street scenes and a city

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.

Chicago showing rides

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Top Woodlawn Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Breakfast was delicious as always. But being in Chicago at this time of year, no AC was needed. LoL. Staff was exceptional! No complaints other than our room was directly in front of the elevator so it was a little loud on occasion 😔 but at the same time, it was convenient. ☺️"
Beverly 3-night trip
Posted 3 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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Frequently asked questions

What's it like in Woodlawn?
Woodlawn is a neighborhood that travelers like for its beaches, restaurants, and gardens. Looking for sights you might find in a travel guide about Woodlawn? Consider a visit to Lake Michigan while you're in the neighborhood.
Where is the best place to stay in Woodlawn?
Based on Expedia customer reviews, Best Motel By OYO Chicago I-90 is the highest ranked property in Woodlawn. This property offers free valet parking and flat-screen TVs.
How many hotels will I be able to find in the Woodlawn area?
If you're searching for places to stay in Chicago, Expedia has something to meet your needs with 46 Woodlawn hotels and other accommodations to choose from.
If I need to cancel my hotel reservation in Woodlawn, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Enter your dates, click on "Search", then use the "fully refundable" filter to view top deals in Woodlawn.
Where can I learn more about changing or cancelling my trip to Woodlawn?
To access more information about updating your trip to Woodlawn or cancelling it, go to https://www.expedia.com/service/.
What can I see and do in this Chicago neighborhood?
Spend some time exploring the great outdoors at Lake Michigan, Jackson Park, and Bob-O-Link Meadow. Lorado Taft's Midway Studios and Jackson Park Driving Range are also a couple of places to visit in the neighborhood. Oak Woods Cemetery, Stony Island Arts Bank, and Rockefeller Memorial Chapel are just a few of the places to visit in and around Woodlawn. While you're out sightseeing in Chicago, be sure to visit other sights like Oriental Institute Museum or Bond Chapel.
How can I get around Woodlawn and the greater Chicago area?
Looking for a quick way to explore more of the city? Catch a ride on metro transit at Cottage Grove Station and King Drive Station. To venture out of town, take a train from Chicago 63rd Street Station.