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Find hotels in Woodlawn, Chicago from ₩107,146

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Discover 4,610 Woodlawn hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Hallway
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 ₩82,489
₩107,146 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Best Motel By OYO Chicago I-90
Terrace/patio
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, (2178)
"Nice Hotel"
United States
Alan
The price is ₩131,658
₩154,553 total
includes taxes & fees
Dec 16 - Dec 17
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3142)
"Amazing and will be staying again!"
United States
Angie
The price is ₩137,874
₩161,851 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Eurostars Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (4848)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is ₩122,496
₩143,797 total
includes taxes & fees
Dec 11 - Dec 12
River Hotel
Ballroom
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, (3438)
"Great hotel located in nice area."
United States
Robert
The price is ₩154,607
₩181,492 total
includes taxes & fees
Dec 14 - Dec 15
Hilton Chicago/Magnificent Mile Suites
Terrace/patio
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, (2257)
"Smooth check in and beautiful hotel"
United States
Monique
The price is ₩141,482
₩216,243 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2947)
"Great location and great staff!!"
United States
lynne
The price is ₩123,733
₩145,250 total
includes taxes & fees
Dec 14 - Dec 15
Aloft Chicago Mag Mile
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (4090)
"I enjoyed my stay with this hotel and would stay here again"
United States
Kim Leticia Terrelle
The price is ₩157,612
₩185,020 total
includes taxes & fees
Dec 14 - Dec 15
citizenM Chicago Downtown
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 10.7 km from Woodlawn
8.4 out of 10, Very Good, (2352)
"We had a great stay and will be back again."
United States
Amber
The price is ₩167,894
₩240,325 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Chicago
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 12.8 km from Woodlawn
8.4 out of 10, Very Good, (4224)
"Great location. "
United States
Rodger
The price is ₩120,787
₩141,792 total
includes taxes & fees
Dec 18 - Dec 19
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 11.3 km from Woodlawn
8.4 out of 10, Very Good, (1004)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is ₩148,774
₩192,324 total
includes taxes & fees
Dec 25 - Dec 26
Holiday Inn & Suites Chicago - Downtown by IHG
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 11.7 km from Woodlawn
9.2 out of 10, Wonderful, (2105)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
River North, 13.1 km from Woodlawn
8.4 out of 10, Very Good, (362)
"love this place definitely coming back !"
United States
Dayanara
The price is ₩96,556
₩113,346 total
includes taxes & fees
Jan 5 - Jan 6, 2026
FOUND Hotel Chicago River North
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1747)
"The location was great!!"
United States
Yvette
The price is ₩125,942
₩147,860 total
includes taxes & fees
Dec 14 - Dec 15
Crowne Plaza Chicago West Loop by IHG
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very Good, (2623)
"Great location "
United States
Stacy
The price is ₩92,534
₩134,564 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Freehand Chicago
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very Good, (9627)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is ₩141,657
₩166,291 total
includes taxes & fees
Dec 22 - Dec 23
Congress Plaza Hotel
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (2928)
"Everything was wonderful-Clean and comfortable beds and extremely good breakfast buffet! "
United States
Nita
The price is ₩145,833
₩212,701 total
includes taxes & fees
Dec 8 - Dec 9
Hotel Riu Plaza Chicago
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 11.7 km from Woodlawn
8.4 out of 10, Very Good, (2119)
"Loved and enjoyed our stay"
United States
Luis
The price is ₩150,984
₩214,064 total
includes taxes & fees
Dec 28 - Dec 29
Palmer House a Hilton Hotel
Rooftop terrace
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4.0 star property
Theatre District, 11.7 km from Woodlawn
9.0 out of 10, Wonderful, (2273)
"Awesome place to stay that was located in the middle of everything! "
United States
Denny
The price is ₩163,798
₩192,282 total
includes taxes & fees
Dec 21 - Dec 22
Hyatt Centric The Loop Chicago
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
River North, 13 km from Woodlawn
7.8 out of 10, Good, (1021)
"Staff was very friendly "
United States
david
The price is ₩125,618
₩147,463 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western River North Hotel
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

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"Great experience "
Duronda 1-night trip
Posted 14 hours ago
Homewood Suites by Hilton Chicago Downtown South Loop

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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.