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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.8 out of 10, (64 reviews)
"Parking was easy. Just a sign in"
United States
David
The price is ₩103,338
₩128,615 total
includes taxes & fees
Apr 28 - Apr 29
Best Motel By OYO Chicago I-90

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, (2,472 reviews)
"Excellent staff, beautiful views."
United States
Daniel
The price is ₩281,080
₩384,463 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2,414 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is ₩218,339
₩296,522 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,137 reviews)
"Very convenient location, kind staff, and comfy rooms. "
United States
Molly Christina
The price is ₩174,420
₩207,380 total
includes taxes & fees
May 25 - May 26
River Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,495 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is ₩317,396
₩430,032 total
includes taxes & fees
May 25 - May 26
Hyatt Regency Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very Good, (10,148 reviews)
"Bed was super comfy and location was great. "
United States
Kelly
The price is ₩196,992
₩234,209 total
includes taxes & fees
May 8 - May 9
Congress Plaza Hotel

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (2,137 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is ₩254,212
₩354,245 total
includes taxes & fees
May 8 - May 9
Fairmont Chicago at Millennium Park

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 11.6 km from Woodlawn
9.2 out of 10, Wonderful, (1,340 reviews)
"We really enjoyed our stay! The staff was incredibly pleasant, and the location was perfect—close to all attractions. Highly recommend!"
United States
Stephanie
The price is ₩259,851
₩308,955 total
includes taxes & fees
May 8 - May 9
Hilton Garden Inn Chicago Central Loop

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, (1,051 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is ₩196,346
₩276,688 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop

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, (3,976 reviews)
"Great hotel, clean an super friendly staff.. would recommend"
United Kingdom
Joel
The price is ₩303,793
₩356,645 total
includes taxes & fees
Apr 30 - May 1
L7 Chicago by LOTTE

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,974 reviews)
"Nice hotel, lovely rooftop bar, good breakfast. Would definitely stay here again."
United States
Rory
The price is ₩217,187
₩299,828 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago

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, (3,664 reviews)
"Comfortable beds and pillows, very friendly staff, location close to everything."
United States
michelle aimee
The price is ₩261,475
₩354,215 total
includes taxes & fees
May 10 - May 11
LondonHouse Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,757 reviews)
"Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by. "
United States
Matt
The price is ₩234,725
₩322,429 total
includes taxes & fees
May 25 - May 26
Hilton Chicago

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, (2,492 reviews)
"Great property, friendly staff, modern room"
United States
Christina
The price is ₩231,581
₩312,250 total
includes taxes & fees
May 8 - May 9
Hyatt Centric The Loop Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,213 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is ₩219,963
₩258,228 total
includes taxes & fees
Apr 30 - May 1
Aloft Chicago Mag Mile

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, (2,244 reviews)
"Super nice staff, nice room, great location. We really enjoyed our stay. "
United States
Jim
The price is ₩176,044
₩254,374 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown

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, (2,785 reviews)
"Clean room, nice staff, good breakfast. "
United States
America.
The price is ₩197,966
₩258,403 total
includes taxes & fees
Apr 30 - May 1
La Quinta Inn & Suites by Wyndham Chicago Downtown

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (2,223 reviews)
"Perfect location great room for the price "
United States
Lisa
The price is ₩194,866
₩228,765 total
includes taxes & fees
Apr 28 - Apr 29
Club Quarters Hotel Wacker at Michigan, Chicago

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, (1,340 reviews)
"Clean rooms friendly staff "
United States
Nasjee
The price is ₩151,101
₩177,390 total
includes taxes & fees
Apr 28 - Apr 29
The Chicago Hotel Collection - Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.6 km from Woodlawn
9.4 out of 10, Exceptional, (2,418 reviews)
"Fantastic location and a luxury hotel for a fair price."
United States
Cornelius
The price is ₩317,544
₩420,879 total
includes taxes & fees
May 25 - May 26
Sofitel Chicago Magnificent Mile
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 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.

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

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 50 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.