Photo by Richard Remington

Woodlawn Hotels near Chicago

    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
Aug 3 - Aug 4
Tomorrow
Aug 4 - Aug 5
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Woodlawn, Chicago

Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2141)
"Location was just what needed and at an affordable price "
The price is P6,219
P10,032 total
includes taxes & fees
Aug 24 - Aug 25
Freehand Chicago
The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very Good, (1063)
"Great place to stay, would definitely recommend and stay here again "
The price is P1,937
P10,463 total
includes taxes & fees
Aug 4 - Aug 5
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile
Rooftop terrace

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1135)
"Enjoyed staying here!"
The price is P1,937
P10,463 total
includes taxes & fees
Aug 4 - Aug 5
The Chicago Hotel Collection - Magnificent Mile
Best Motel By OYO Chicago I-90
Hallway

Best Motel By OYO Chicago I-90

2.0 star property
3.2 out of 10, (32)
"Easy, safe parking "
The price is P4,055
P4,906 total
includes taxes & fees
Sep 2 - Sep 3
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, (2054)
"Beautiful property, will definitely stay there again."
The price is P10,552
P14,073 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (3628)
"Great stay. "
The price is P8,355
P9,808 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1291)
"A wonderful hotel in a great location!"
The price is P10,941
P14,550 total
includes taxes & fees
Aug 5 - Aug 6
Claridge House
Ameristar Casino Hotel East Chicago
Lobby

Ameristar Casino Hotel East Chicago

4.0 star property
8.4 out of 10, Very Good, (1007)
"Very nice and the staff"
The price is P6,979
P8,398 total
includes taxes & fees
Sep 1 - Sep 2
Ameristar Casino Hotel East Chicago
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (539)
"It was a wonderful place to stay! "
The price is P3,926
P9,383 total
includes taxes & fees
Aug 4 - Aug 5
The Chicago Hotel Collection River North
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1922)
"Great stay"
The price is P7,387
P10,037 total
includes taxes & fees
Aug 24 - Aug 25
Millennium Knickerbocker Chicago
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2567)
"Great location and hotel!"
The price is P8,355
P9,808 total
includes taxes & fees
Aug 17 - Aug 18
Hilton Chicago/Magnificent Mile Suites
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2273)
"Location, cleanness and staff were very good "
The price is P6,224
P7,306 total
includes taxes & fees
Aug 25 - Aug 26
Travelodge by Wyndham Downtown Chicago
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, sun loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1954)
"Very pleasant stay!"
The price is P9,260
P10,870 total
includes taxes & fees
Sep 1 - Sep 2
DoubleTree by Hilton Chicago - Magnificent Mile
Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1009)
"Great stay"
The price is P7,852
P9,218 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Chicago - Magnificent Mile by IHG
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1028)
"Good budget hotel"
The price is P7,169
P8,415 total
includes taxes & fees
Aug 24 - Aug 25
Best Western River North Hotel
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2573)
"Good location and excellent staff and service."
The price is P6,872
P8,067 total
includes taxes & fees
Sep 2 - Sep 3
Best Western Grant Park Hotel
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2778)
"We love our stay here !"
The price is P7,102
P8,337 total
includes taxes & fees
Aug 17 - Aug 18
Aloft Chicago Mag Mile
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1007)
"Great place to stay!"
The price is P7,166
P8,412 total
includes taxes & fees
Aug 24 - Aug 25
Ohio House Motel
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very Good, (165)
"Great stay"
The price is P6,415
P7,531 total
includes taxes & fees
Aug 24 - Aug 25
FOUND Hotel Chicago River North
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, (1988)
"Friendly staff, clean and great location. We’ll definitely stay here again."
The price is P7,678
P9,013 total
includes taxes & fees
Sep 1 - Sep 2
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
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 and neighborhoods for the activities you enjoy most.
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

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

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

The Loop

Michigan Avenue and Lake Michigan 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.

Lincoln Park featuring modern architecture and a city
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.

Top Woodlawn Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"A holiday. 6 nights. We were upgrade on arrival, the staff were very friendly & Helpful. The room was clean & very comfortable with all the amenities you would expect. There was plenty of hanging & draw space as well as room for cosmetics & toiletries In the bathroom. We enjoyed our stay & would definitely recommend. "
Daniel 6-night trip
Posted 2 hours ago
The Royal Sonesta Chicago Downtown

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 43 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?

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.