A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

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Check prices for these dates

This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

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Our top choices for Woodlawn hotels

Lobby

1. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (113 reviews)
"Clean room"
United States
Roger
The price is ￥12,976
￥15,230 total
includes taxes & fees
Sep 3 - Sep 4
Best Motel By OYO Chicago I-90
Restaurant

2. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 10.3 km from Woodlawn
8.2 out of 10, Very Good, (2,762 reviews)
"Good stay!"
United States
Adit
The price is ￥22,577
￥26,843 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Grant Park Hotel
Lobby

3. River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,410 reviews)
"Great location and nice hotel, very helpful and friendly staff."
United Arab Emirates
Yousef
The price is ￥20,222
￥24,042 total
includes taxes & fees
Aug 9 - Aug 10
River Hotel
Exterior

4. 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, (2,479 reviews)
"Excelente hotel"
Mexico
Evelyn
The price is ￥24,650
￥29,307 total
includes taxes & fees
Aug 30 - Aug 31
Crowne Plaza Chicago West Loop by IHG
Lunch, dinner and brunch served

5. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
River North, 12.8 km from Woodlawn
9.2 out of 10, Wonderful, (1,893 reviews)
"Great location, good breakfast and super nice staff"
United States
Michelle
The price is ￥26,819
￥31,886 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Chicago/River North
Exterior

6. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.1 km from Woodlawn
9.6 out of 10, Exceptional, (1,302 reviews)
"Very helpful front desk staff and friendly cleaners. Very pleasant stay"
United States
Aleace
The price is ￥26,377
￥31,359 total
includes taxes & fees
Sep 7 - Sep 8
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Nightclub

7. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.8 out of 10, Excellent, (3,620 reviews)
"Great location, clean room, and friendly staff"
United States
Kelli
The price is ￥18,909
￥22,482 total
includes taxes & fees
Aug 9 - Aug 10
Club Quarters Hotel, Central Loop, Chicago
Suite, 1 Bedroom, Corner | Private kitchen | Coffee/tea maker, full-size fridge, microwave, stovetop

8. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (2,410 reviews)
"Great stay"
United Kingdom
jayne
The price is ￥25,344
￥29,754 total
includes taxes & fees
Sep 7 - Sep 8
Homewood Suites by Hilton Chicago Downtown South Loop
Lobby

9. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.6 out of 10, Good, (2,737 reviews)
"Great location, clean rooms, would stay here again!"
United States
Adam
The price is ￥18,256
￥21,704 total
includes taxes & fees
Aug 30 - Aug 31
Travelodge by Wyndham Downtown Chicago
2 bars/lounges

10. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,501 reviews)
"Great hotel in great location"
United States
Emily
The price is ￥35,497
￥47,857 total
includes taxes & fees
Aug 30 - Aug 31
Hyatt Regency Chicago
55-inch LCD TV with cable channels, TV, pay movies

11. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.3 km from Woodlawn
9.6 out of 10, Exceptional, (4,519 reviews)
"Great stay"
United States
Julie Ann
The price is ￥29,763
￥35,384 total
includes taxes & fees
Aug 9 - Aug 10
L7 Chicago by LOTTE
Indoor wedding

12. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,551 reviews)
"Great stay"
United States
Isaac
The price is ￥42,309
￥55,883 total
includes taxes & fees
Aug 16 - Aug 17
Swissotel - Chicago
City view from property

13. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
12.7 km from Woodlawn
9.0 out of 10, Wonderful, (1,319 reviews)
"Very nice hotel"
United States
Hadi
The price is ￥32,169
￥38,248 total
includes taxes & fees
Aug 23 - Aug 24
Hyatt House Chicago/West Loop-Fulton Market
Terrace/patio

14. 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, (2,645 reviews)
"Great stay."
United States
Dawn
The price is ￥27,630
￥38,288 total
includes taxes & fees
Sep 7 - Sep 8
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior

15. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 12 km from Woodlawn
8.8 out of 10, Excellent, (1,506 reviews)
"Enjoyed my stay!"
United States
Kimberly
The price is ￥28,397
￥33,761 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Chicago/Downtown - The Loop
Exterior

16. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 11.9 km from Woodlawn
8.6 out of 10, Excellent, (2,872 reviews)
"This property is so nice to stay at, will continue to stay here in the future."
United States
Paige
The price is ￥22,575
￥29,654 total
includes taxes & fees
Sep 8 - Sep 9
La Quinta Inn & Suites by Wyndham Chicago Downtown
Rooftop terrace

17. 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, (2,687 reviews)
"Great location"
United States
Dee
The price is ￥29,475
￥39,005 total
includes taxes & fees
Aug 23 - Aug 24
Hyatt Centric The Loop Chicago
Room service - dining

18. The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (1,988 reviews)
"Great stay and friendly staff!"
Canada
Richard
The price is ￥26,661
￥31,699 total
includes taxes & fees
Aug 23 - Aug 24
The Wade
Front of property

19. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (4,951 reviews)
"Very nice and rooms were amazing. Loved the location and the breakfast buffet!"
United States
Cicely
The price is ￥31,298
￥41,708 total
includes taxes & fees
Sep 7 - Sep 8
Hotel Riu Plaza Chicago
Terrace/patio

20. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
12.4 km from Woodlawn
9.2 out of 10, Wonderful, (1,014 reviews)
"Great location"
United States
Carmen
The price is ￥21,417
￥25,464 total
includes taxes & fees
Aug 23 - Aug 24
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
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.
A busy city street with tall buildings, a bus, and cars.

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.

A river with yellow boats, a bridge, and tall buildings.

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.

A historic castle-like building with intricate stonework and a paved walkway.

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.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

The Chicago Theatre with illuminated marquee and a wet street reflecting lights.
Photo by Mattyboy876
Open Photo by Mattyboy876

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

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

8/10 Good
"Was fine for a two night stay. Probably wouldn’t have booked if I had known the bathroom door was see through though. Not everyone is staying alone or sharing a room with someone they are comfortable with seeing almost everything through the door. So would not book again."
Emma 2-night trip
Posted 2 hours ago
Club Quarters Hotel, Central Loop, Chicago

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 49 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. Obama Presidential Center and 63rd Street Beach are also a couple of places to visit in the neighborhood. Oak Woods Cemetery, Lorado Taft's Midway Studios, and Stony Island Arts Bank 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 Rockefeller Memorial Chapel or Oriental Institute Museum.
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.

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