Photo by Richard Remington

Hotels in Woodlawn

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels in Woodlawn

River Hotel
View from property
River Hotel
4.0 star property
8.6 out of 10, Excellent, (3555)
"I can't say enough good things about this hotel—it's truly the best for families! If you're hoping for the convenience of free laundry, a dryer, and detergent, this is definitely the place to choose. We traveled light since we were flying basic economy, and doing laundry every other night was so easy here. The staff were fantastic, and I loved the complimentary green tea, coffee, and cappuccino available on the second level. We stayed in a deluxe room with two queen beds, which was perfect for...
The price is S$181
includes taxes & fees
25 Nov - 26 Nov
River Hotel
Eurostars Magnificent Mile
Lobby lounge
Eurostars Magnificent Mile
4.0 star property
8.6 out of 10, Excellent, (2728)
"Great stay!"
The price is S$174
includes taxes & fees
24 Nov - 25 Nov
Eurostars Magnificent Mile
Hotel Riu Plaza Chicago
Front of property
Hotel Riu Plaza Chicago
4.0 star property
9.2 out of 10, Wonderful, (897)
"Absolutely loved this hotel and the breakfast was amazing!!!!"
The price is S$215
includes taxes & fees
26 Nov - 27 Nov
Hotel Riu Plaza Chicago
Congress Plaza Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (8086)
"Good stay "
The price is S$211
includes taxes & fees
7 Nov - 8 Nov
Congress Plaza Hotel
Freehand Chicago
Cocktail bar
Freehand Chicago
4.0 star property
7.8 out of 10, Good, (1467)
"Ok"
The price is S$136
includes taxes & fees
26 Nov - 27 Nov
Freehand Chicago
L7 Chicago by LOTTE
Exterior
L7 Chicago by LOTTE
4.5 star property
9.6 out of 10, Exceptional, (934)
"Perfect hotel for families and couples "
The price is S$250
includes taxes & fees
25 Nov - 26 Nov
L7 Chicago by LOTTE
citizenM Chicago Downtown
Terrace/patio
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (2195)
"I enjoyed my stay at CitizenM. Loved the interesting and vibrant art collection and books throughout. The rooms are high tech, cozy, and the location is perfect!"
The price is S$153
includes taxes & fees
25 Nov - 26 Nov
citizenM Chicago Downtown
Hyatt Centric The Loop Chicago
Rooftop terrace
Hyatt Centric The Loop Chicago
4.0 star property
8.8 out of 10, Excellent, (1389)
"I had a great time at the Hyatt! The staff was super friendly and helpful and the room was lovely. Only note I have is it could include a microwave. Thank you for a wonderful stay!"
The price is S$163
includes taxes & fees
25 Nov - 26 Nov
Hyatt Centric The Loop Chicago
Hotel Felix River North/Magnificent Mile
Lobby sitting area
Hotel Felix River North/Magnificent Mile
4.0 star property
8.0 out of 10, Very good, (1231)
"Rooms were a little small but overall nice space."
The price is S$183
includes taxes & fees
10 Nov - 11 Nov
Hotel Felix River North/Magnificent Mile
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, (1821)
"No complaints "
The price is S$166
includes taxes & fees
25 Nov - 26 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago
Premium bedding, in-room safe, desk, laptop workspace
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3274)
"Hotel was great but Expedia noted there was free parking. Had to pay $25 for parking four blocks away "
The price is S$171
includes taxes & fees
24 Nov - 25 Nov
Club Quarters Hotel, Central Loop, Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.2 out of 10, Very good, (2569)
"Nice place"
The price is S$179
includes taxes & fees
25 Nov - 26 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
The Whitehall Hotel, BW Premier Collection
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.2 out of 10, Very good, (3433)
"Great location "
The price is S$145
includes taxes & fees
25 Nov - 26 Nov
The Whitehall Hotel, BW Premier Collection
voco Chicago Downtown, an IHG Hotel
City view from property
voco Chicago Downtown, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1945)
"Loved it"
The price is S$181
includes taxes & fees
25 Nov - 26 Nov
voco Chicago Downtown, an IHG Hotel
The Royal Sonesta Chicago Downtown
Exterior
The Royal Sonesta Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (2215)
"Great stay and location "
The price is S$265
includes taxes & fees
25 Nov - 26 Nov
The Royal Sonesta Chicago Downtown
Trump International Hotel & Tower Chicago
Terrace/patio
Trump International Hotel & Tower Chicago
5.0 star property
9.4 out of 10, Exceptional, (1431)
"Great!"
The price is S$610
includes taxes & fees
17 Nov - 18 Nov
Trump International Hotel & Tower Chicago
Palmer House a Hilton Hotel
Meeting facility
Palmer House a Hilton Hotel
4.0 star property
8.2 out of 10, Very good, (1512)
"The Palmer House is a beautiful place in the perfect location. Easy walking to parks, the Lake Shore, museums and restaurants. Will definitely choose it again on a trip to Chicago. "
The price is S$234
includes taxes & fees
24 Nov - 25 Nov
Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North
Lobby
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.2 out of 10, Very good, (3182)
"It was perfect. We will be back. "
The price is S$183
includes taxes & fees
25 Nov - 26 Nov
Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago
Exterior
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (1446)
"good views"
The price is S$285
includes taxes & fees
24 Nov - 25 Nov
Hilton Chicago
Virgin Hotels Chicago
Rooftop terrace
Virgin Hotels Chicago
4.5 star property
9.2 out of 10, Wonderful, (1214)
"Great location and over vibe. "
The price is S$347
includes taxes & fees
5 Dec - 6 Dec
Virgin Hotels 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.
Don't see what you're looking for?
See all available properties in Woodlawn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 28 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.