Photo by Richard Remington

Hotels in Woodlawn

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
24 Jun - 25 Jun
Tomorrow
25 Jun - 26 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels in Woodlawn

Best Motel By OYO Chicago I-90
Reception

Best Motel By OYO Chicago I-90

2.0 star property
3.4 out of 10, (21)
"Ghetto property stay away from here "
The price is S$157
includes taxes & fees
7 Jul - 8 Jul
Best Motel By OYO Chicago I-90
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2058)
"Amazing stay"
The price is S$313
includes taxes & fees
6 Jul - 7 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Reception

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2273)
"Beautiful hotel"
The price is S$268
includes taxes & fees
1 Jul - 2 Jul
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1468)
"Great location and rooms "
The price is S$295
includes taxes & fees
30 Jun - 1 Jul
Loews Chicago Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1880)
"Very nice hotel and very clean"
The price is S$216
includes taxes & fees
30 Jun - 1 Jul
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1453)
"Stayed here a few times and its always great. "
The price is S$317
includes taxes & fees
30 Jun - 1 Jul
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Executive lounge

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1796)
"Great stay, great location and very polite staff "
The price is S$321
includes taxes & fees
29 Jun - 30 Jun
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2757)
"Good location, comfortable bed, staff very nice and helpful!"
The price is S$188
includes taxes & fees
29 Jun - 30 Jun
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.6 out of 10, Excellent, (1004)
"The Ivy Hotel was so nice! It was very roomy and had everything to make our stay convenient and special! "
The price is S$177
includes taxes & fees
1 Jul - 2 Jul
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1851)
"Very close to downtown, helpful staff, excellent breakfast"
The price is S$212
includes taxes & fees
21 Jul - 22 Jul
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3263)
"Amazing location and super friendly staff "
The price is S$309
includes taxes & fees
29 Jun - 30 Jun
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2338)
"Great stay "
The price is S$204
includes taxes & fees
6 Jul - 7 Jul
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.4 out of 10, Very good, (1846)
"The staff were brilliant, particularly the breakfast crew in the restaurant. "
The price is S$217
includes taxes & fees
1 Jul - 2 Jul
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Exterior

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1022)
"A great place to stay"
The price is S$283
includes taxes & fees
6 Jul - 7 Jul
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Restaurant

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1099)
"Lovely stay in the king suite. "
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1635)
"Great stay"
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2063)
"Absolutely stunning place to stay. "
The price is S$231
includes taxes & fees
30 Jun - 1 Jul
Hotel Riu Plaza Chicago
The Blackstone, Autograph Collection
View from property

The Blackstone, Autograph Collection

4.0 star property
9.0 out of 10, Wonderful, (1003)
"Close to major tourist attractions. Hotel rooms are tired. "
The price is S$263
includes taxes & fees
29 Jun - 30 Jun
The Blackstone, Autograph Collection
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2534)
"Great stay"
The price is S$173
includes taxes & fees
30 Jun - 1 Jul
Best Western Grant Park Hotel
Super 8 by Wyndham South Holland
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Super 8 by Wyndham South Holland

2.0 star property
7.4 out of 10, Good, (1010)
"Hotel was very clean and room service was great as well"
The price is S$111
includes taxes & fees
6 Jul - 7 Jul
Super 8 by Wyndham South Holland
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most. Learn more about Woodlawn
Learn more about Woodlawn
Downtown Chicago which includes a city
Downtown Chicago map

Downtown Chicago

2 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile - River North
Magnificent Mile map

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop - Downtown featuring a river or creek
The Loop map

The Loop

Michigan Avenue and Art Institute of Chicago are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

River North map

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Chicago which includes a city and modern architecture
Lincoln Park map

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Frequently asked questions

What's it like in Woodlawn?

Woodlawn is a neighbourhood that travellers 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 neighbourhood.

How many hotels are there in the Woodlawn area?

If you're searching for places to stay in Chicago, Expedia has something to meet your needs with 40 Woodlawn hotels and other accommodation options to choose from.

If I need to cancel my hotel reservation in Woodlawn, will I receive a refund?

Yes, the majority of hotel room reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Enter dates in and click on "Search", then filter by "fully refundable" to view the best deals available in Woodlawn.

What can I see and do in this Chicago neighbourhood?

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 neighbourhood. 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, make sure that you visit other sights such as Oriental Institute Museum or Bond Chapel.

How can I get around Woodlawn and the greater Chicago area?

Ready to get out and explore the city? Cottage Grove Station is the closest metro station. To venture out of town, take a train from Chicago 63rd Street Station.