Photo by Richard Remington

Woodlawn Hotels, Chicago

Most accommodation are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Filter by

Popular filters
Popular filters
Total price
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

3989 Cheap Hotels in Woodlawn - Specials, Reviews, & Last Minute Deals

Lobby
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (1601)
"Enjoyed my stay here. It’s in the downtown loop making taking the train convenient. Many things are walkable nearby that are great for tourists. Staff was incredibly friendly and helpful!"
The price is NZ$313
per night
27 May - 28 May
Silversmith Hotel Chicago Downtown
Terrace/patio
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (1349)
"We enjoyed the room so much!! It’s so quaint and clean. We were able to rest so comfortably and enjoyed every minute of it! I would come back and I will for sure tell everyone "
The price is NZ$242
per night
27 May - 28 May
citizenM Chicago Downtown
Lobby
LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
9.2 out of 10, Wonderful, (3515)
"The roof top bar-views are second to none. Property is directly on river walk and steps from Michigan Ave and all the shopping one can stand. Hotel is modern and classy!!"
The price is NZ$395
per night
27 May - 28 May
LondonHouse Chicago, Curio Collection by Hilton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.2 out of 10, Wonderful, (1897)
"Everything was great!! I’d stay here again for sure. "
The price is NZ$413
per night
28 May - 29 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Rooftop terrace
Virgin Hotels Chicago
4.5 star property
9.2 out of 10, Wonderful, (1004)
"We have a plenty staying at this hotel has the best locations and restaurant is so good "
The price is NZ$445
per night
27 May - 28 May
Virgin Hotels Chicago
Terrace/patio
Trump International Hotel & Tower Chicago
5.0 star property
9.2 out of 10, Wonderful, (1190)
"Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago "
The price is NZ$712
per night
23 May - 24 May
Trump International Hotel & Tower Chicago
Exterior
Loews Chicago Hotel
4.5 star property
9.2 out of 10, Wonderful, (1509)
"Fantastic property!!"
The price is NZ$327
per night
27 May - 28 May
Loews Chicago Hotel
Exterior
Hyatt Regency Chicago
4.0 star property
9.0 out of 10, Wonderful, (3489)
"Overall a great experience "
The price is NZ$441
per night
28 May - 29 May
Hyatt Regency Chicago
Exterior
The Royal Sonesta Chicago Downtown
4.0 star property
9.0 out of 10, Wonderful, (1924)
"The front desk person was great in assisting me to shorten my stay. She was polite, professional, and efficient. Thx"
The price is NZ$367
per night
27 May - 28 May
The Royal Sonesta Chicago Downtown
Cocktail bar
ACME Hotel Company
3.5 star property
9.0 out of 10, Wonderful, (1405)
"Hotel was decently cleaned. The rooms were comfortable but the pillows and bed weren’t the most comfortable. Most rooms do not have a view. They do not clean your room everyday unless you request it which sucks cause I didn’t know that. Toiletries were not great either, so come with your stuff. Overall it’s a great stay for the price and SUPER awesome location. You can walk everywhere from it, so for that reason I’d stay again. "
The price is NZ$245
per night
27 May - 28 May
ACME Hotel Company
Exterior
Hyatt Place Chicago/River North
3.5 star property
9.0 out of 10, Wonderful, (1378)
"It was amazing. "
The price is NZ$297
per night
27 May - 28 May
Hyatt Place Chicago/River North
Aerial view
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1004)
"Comfortable stay friendly staff"
The price is NZ$324
per night
27 May - 28 May
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Lobby
Hyatt Centric Chicago Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (1297)
"The hotel was fine. It is extremely central to most usual tourist activities and worked really well in that regard. It has a weird entryway that you enter on the ground floor that is not the hotel and you go up a floor or so and then enter the hotel lobby. They have disposable plastic cups further wrapped in plastic instead of real drinking glasses. This was unusual and felt cheap. They have paper cups instead of real coffee cups which is less uncommon. Both of these felt eco unfriendly....
The price is NZ$340
per night
27 May - 28 May
Hyatt Centric Chicago Magnificent Mile
Daily cooked-to-order breakfast for a fee
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2199)
"It was a perfect location "
The price is NZ$286
per night
27 May - 28 May
Aloft Chicago Mag Mile
Front of property - evening/night
Fairmont Chicago at Millennium Park
4.5 star property
8.6 out of 10, Excellent, (1486)
"Requested a fridge and microwave, as they do not come in each room. Wasn't there when we checked in, but came shortly and worked well. Nice hotel, but no pool and they only offer parking as a valet service for $80+ per day. Ended up parking at Aon Center for $17/day, which was VERY close. "
The price is NZ$367
per night
27 May - 28 May
Fairmont Chicago at Millennium Park
Rooftop bar, al fresco dining, open daily
The Godfrey Hotel Chicago
4.5 star property
8.6 out of 10, Excellent, (1533)
"N/a"
The price is NZ$292
per night
29 May - 30 May
The Godfrey Hotel Chicago
Terrace/patio
Home2 Suites by Hilton Chicago River North
3.0 star property
8.4 out of 10, Very good, (1488)
"Nice location, nice staff."
The price is NZ$312
per night
27 May - 28 May
Home2 Suites by Hilton Chicago River North
Balcony
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very good, (1928)
"Very nice and clean! Great customer service."
The price is NZ$345
per night
27 May - 28 May
Eurostars Magnificent Mile
Exterior
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (1020)
"It's a large hotel with history. Room is fair at this price. "
The price is NZ$317
per night
27 May - 28 May
Hilton Chicago
Front of property - evening/night
The Drake
4.0 star property
8.4 out of 10, Very good, (1004)
"What a beautiful hotel full of history and elegance. I wish that something would have been offered for breakfast. (A croissant, bagel or even toast and fruit). But otherwise the stay was very pleasant and they worked to accommodate my room to be close to my daughter and grandson."
The price is NZ$296
per night
27 May - 28 May
The Drake
Don't see what you're looking for?
See all available properties in Woodlawn
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.

Other neighbourhoods around Woodlawn

Hotels Near Chicago, Illinois Learn more about Woodlawn
Downtown Chicago featuring a city

Downtown Chicago

4 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 Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Woodlawn hotels information

Number of reviews
43,242
Accommodation
3,989 hotels
Lowest Price
NZ$195
Highest Price
NZ$445

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 27 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.

Recent Reviews in Woodlawn

Congress Plaza Hotel

Congress Plaza Hotel

5/5 Excellent
"Very nice, beautiful hotel. The staff is amazing, both friendly and professional. My only issue was the shower, which we found lacking in both temperature and water pressure. It wasn’t a major problem, and somewhat understandable given the age of the hotel. Otherwise, it was a great stay."
A verified traveller stayed at Congress Plaza Hotel
Posted 21 hours ago
Congress Plaza Hotel