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

Find hotels in Woodlawn, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Jun 26 - Jun 28
Next weekend
Jul 3 - Jul 5

Filter by

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Property class

Our top choices for Woodlawn hotels

Room, 2 Double Beds, Smoking | Bathroom | Free toiletries, towels

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (89 reviews)
"This is not a good place."
United States
Dinesh Kumar
The price is ￥14,820
￥18,880 total
includes taxes & fees
Jul 7 - Jul 8
Best Motel By OYO Chicago I-90
2 bars/lounges, rooftop bar

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1,013 reviews)
"Great hotel to stay."
United States
Josias
The price is ￥30,831
￥41,389 total
includes taxes & fees
Jun 29 - Jun 30
theWit Chicago, a Hilton Hotel
Breakfast and dinner served

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.1 km from Woodlawn
9.2 out of 10, Wonderful, (1,821 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is ￥20,518
￥29,764 total
includes taxes & fees
Jul 8 - Jul 9
Omni Chicago Hotel
2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3,755 reviews)
"Great location!"
United States
William
The price is ￥36,533
￥48,170 total
includes taxes & fees
Jun 30 - Jul 1
LondonHouse Chicago, Curio Collection by Hilton
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very Good, (10,163 reviews)
"Great stay!"
United States
Daniel
The price is ￥22,000
￥26,156 total
includes taxes & fees
Jun 29 - Jun 30
Congress Plaza Hotel
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,412 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is ￥23,098
￥33,142 total
includes taxes & fees
Jul 1 - Jul 2
Swissotel - Chicago
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,453 reviews)
"Staff was great."
United States
Marianne
The price is ￥35,486
￥47,944 total
includes taxes & fees
Jul 6 - Jul 7
Hyatt Regency Chicago
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, (2,264 reviews)
"Wonderful stay"
United States
Taylor
The price is ￥18,722
￥27,181 total
includes taxes & fees
Jul 5 - Jul 6
Silversmith Hotel Chicago Downtown
Rooftop bar, alfresco dining, open daily

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 13.3 km from Woodlawn
8.8 out of 10, Excellent, (2,279 reviews)
"Would definitely stay there again"
United States
Benjy
The price is ￥21,050
￥28,652 total
includes taxes & fees
Jul 1 - Jul 2
The Godfrey Hotel Chicago
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 11.9 km from Woodlawn
9.4 out of 10, Exceptional, (1,109 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is ￥25,605
￥35,225 total
includes taxes & fees
Jul 1 - Jul 2
Staypineapple, An Iconic Hotel, The Loop
Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1,417 reviews)
"The location is great and the rooms are comfortable and spacious. The free yoga classes were a nice bonus. It is clear that the hotel is going through a transition."
Canada
Caroline
The price is ￥29,599
￥39,792 total
includes taxes & fees
Jun 30 - Jul 1
Sports Illustrated Resorts Chicago
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 11.7 km from Woodlawn
8.6 out of 10, Excellent, (2,495 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is ￥36,131
￥47,751 total
includes taxes & fees
Jun 30 - Jul 1
Palmer House a Hilton Hotel
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,670 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is ￥25,808
￥30,683 total
includes taxes & fees
Jun 28 - Jun 29
Eurostars Magnificent Mile
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,188 reviews)
"Great hotel with awesome location"
United States
Daniel
The price is ￥20,837
￥24,773 total
includes taxes & fees
Jul 1 - Jul 2
Central Loop Hotel
Ballroom

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3,476 reviews)
"Incredible location, comfortable rooms, great bar and a restaurant attached! Loved staying here!"
United States
Feng
The price is ￥28,889
￥39,506 total
includes taxes & fees
Jul 5 - Jul 6
The Royal Sonesta Chicago Downtown
Presidential Suite, 1 Bedroom, Non Smoking | Premium bedding, in-room safe, desk, blackout drapes

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
River North, 13 km from Woodlawn
8.8 out of 10, Excellent, (1,578 reviews)
"Great stay"
United States
Matt
The price is ￥22,743
￥31,834 total
includes taxes & fees
Jul 1 - Jul 2
Hotel 55 Chicago Downtown
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,686 reviews)
"Location was great"
United States
Pamela
The price is ￥38,551
￥51,586 total
includes taxes & fees
Jul 1 - Jul 2
Sheraton Grand Chicago Riverwalk
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,256 reviews)
"Excellent place to stay, as we found it central & walkable to most parks & attractions. The place was spotless & the staff were fantastic."
Canada
Jody
The price is ￥22,071
￥26,239 total
includes taxes & fees
Jul 1 - Jul 2
River Hotel
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (2,051 reviews)
"Great room and view. Clean, near by Grant park, great staff."
United States
Kimberly
The price is ￥27,140
￥32,265 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Garden Inn Chicago Downtown South Loop
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 14.4 km from Woodlawn
8.2 out of 10, Very Good, (1,629 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is ￥21,150
￥25,147 total
includes taxes & fees
Jul 2 - Jul 3
The Chicago Hotel Collection Ambassador Gold Coast
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.
View all properties

Where to stay in Woodlawn

Find the best Woodlawn 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.

A river with a city skyline in the background, surrounded by green trees and grass.

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 Woodlawn Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Great stay. Clean rooms. Excellent customer service."
Petina 3-night trip
Posted 1 hour ago
Crowne Plaza Chicago West Loop by IHG

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. 63rd Street Beach and Lorado Taft's Midway Studios 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.

Explore a world of travel with Expedia