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Discover 4,572 Woodlawn hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Best Motel By OYO Chicago I-90
Stairwell with a metal railing and large window featuring a decorative pattern.

Best Motel By OYO Chicago I-90

2.0 star property
3.2 out of 10, (33)
"Easy, safe parking "
The price is NT$2,075
NT$2,704 total
includes taxes & fees
Sep 7 - Sep 8
Best Motel By OYO Chicago I-90
River Hotel
Elevators lead to upper floors from this grand corridor, flanked by ornate columns.

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4498)
"Great place to stay."
The price is NT$4,971
NT$5,835 total
includes taxes & fees
Aug 17 - Aug 18
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1966)
"Great place !"
The price is NT$4,738
NT$5,562 total
includes taxes & fees
Sep 1 - Sep 2
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Enjoy a meal with a view at this restaurant, offering a variety of seating options and a central bar area.

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3060)
"Great stay!"
The price is NT$4,763
NT$5,591 total
includes taxes & fees
Sep 1 - Sep 2
Eurostars Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2060)
"Beautiful property, will definitely stay there again."
The price is NT$5,153
NT$6,912 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
citizenM Chicago Downtown
Experience the vibrant city atmosphere in this urban oasis, featuring a striking geometric-patterned awning and modern architecture.

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3534)
"Would love to stay here again!"
The price is NT$4,655
NT$5,464 total
includes taxes & fees
Aug 26 - Aug 27
citizenM Chicago Downtown
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Experience the sleek, modern architecture of this urban hotel, featuring a prominent marquee sign and vertical windows.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (3636)
"Great stay. "
The price is NT$4,567
NT$5,362 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel
Experience grandeur in this beautifully designed ballroom with high ceilings, arched windows, and elegant table settings.

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8924)
"Great place to stay."
The price is NT$7,494
NT$8,797 total
includes taxes & fees
Sep 7 - Sep 8
Congress Plaza Hotel
Freehand Chicago
Relax in style with plush seating and a classic design, featuring a sofa, armchairs, and a bookshelf.

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2171)
"Good spot when staying for lolla "
The price is NT$3,324
NT$5,299 total
includes taxes & fees
Aug 18 - Aug 19
Freehand Chicago
Hilton Chicago/Magnificent Mile Suites
Enjoy a sophisticated dining experience with a beautifully set table and city view.

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2592)
"Great location and hotel!"
The price is NT$4,276
NT$5,019 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Chicago/Magnificent Mile Suites
Aloft Chicago Mag Mile
Conference room with a large, round table and six chairs, offering city views.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2780)
"We love our stay here !"
The price is NT$4,137
NT$4,857 total
includes taxes & fees
Aug 24 - Aug 25
Aloft Chicago Mag Mile
Best Western River North Hotel
Relax on the rooftop with wicker lounge chairs and take in the city skyline views.

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1026)
"Great location "
The price is NT$3,770
NT$4,425 total
includes taxes & fees
Aug 24 - Aug 25
Best Western River North Hotel
Holiday Inn & Suites Chicago - Downtown by IHG
Relax by the rooftop pool with a stunning view of the city skyline.

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very Good, (1010)
"I was happy with my stay. Clean rooms and friendly staff"
The price is NT$4,405
NT$5,528 total
includes taxes & fees
Sep 3 - Sep 4
Holiday Inn & Suites Chicago - Downtown by IHG
Hilton Chicago
Classic hotel with a symmetrical facade and central entrance.

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2053)
"Enjoyed our stay. Great location."
The price is NT$4,165
NT$5,762 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Chicago
Crowne Plaza Chicago West Loop by IHG
Relax in a casual, urban setting with seating areas and a prominent counter for ordering.

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.8 out of 10, Excellent, (1361)
"Staff was so friendly and the rooms were really clean!"
The price is NT$4,226
NT$4,961 total
includes taxes & fees
Aug 24 - Aug 25
Crowne Plaza Chicago West Loop by IHG
Holiday Inn Express Chicago - Magnificent Mile by IHG
Hotel facade with a balcony featuring a variety of flowers and large windows with metal railings.

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1006)
"Great stay"
The price is NT$4,018
NT$4,717 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Chicago - Magnificent Mile by IHG
Palmer House a Hilton Hotel
Experience the grandeur of our elegantly decorated lobby, featuring a stunning chandelier, comfortable seating areas, and intricate designs.

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very Good, (1836)
"Nice place to stay"
The price is NT$5,161
NT$6,803 total
includes taxes & fees
Sep 4 - Sep 5
Palmer House a Hilton Hotel
FOUND Hotel Chicago River North
Experience the vibrant atmosphere of this historic building, featuring ornate details and a lively dining and entertainment area.

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very Good, (176)
"Great stay"
The price is NT$3,054
NT$3,585 total
includes taxes & fees
Aug 10 - Aug 11
FOUND Hotel Chicago River North
La Quinta Inn & Suites by Wyndham Chicago Downtown
Experience the vibrant city at La Quinta Inn & Suites, offering a variety of rooms with city views.

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2462)
"Had a wonderful stay here and staff was super friendly!"
The price is NT$4,259
NT$5,524 total
includes taxes & fees
Aug 24 - Aug 25
La Quinta Inn & Suites by Wyndham Chicago Downtown
Travelodge by Wyndham Downtown Chicago
Relax in the hotel lobby's spacious seating area, surrounded by a city view and comfortable sofas and armchairs.

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2281)
"Hotel location, staff and transportation were very good "
The price is NT$2,839
NT$3,333 total
includes taxes & fees
Aug 25 - Aug 26
Travelodge by Wyndham Downtown Chicago
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.
Downtown Chicago showing a city
Downtown Chicago map

Downtown Chicago

2 out of top 10 points of interest in this area

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 - River North
Magnificent Mile map

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 - Downtown which includes a river or creek
The Loop map

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 showing railway items, street scenes and a city
River North map

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.

Chicago which includes modern architecture and a city
Lincoln Park map

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

The Wade

The Wade

10/10 Excellent
"Great comfortable clean room with a spectacular view! "
William 3-night trip
Posted 6 hours ago
The Wade

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.