A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

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Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (94 reviews)
"This is not a good place."
United States
Dinesh Kumar
The price is £88
includes taxes & fees
16 Jul - 17 Jul
Best Motel By OYO Chicago I-90

The Wade

The Wade
4.5 star property
Streeterville, 8 mi from Woodlawn
8.6 out of 10, Excellent, (1,876 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is £151
includes taxes & fees
6 Jul - 7 Jul
The Wade

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.7 mi from Woodlawn
8.6 out of 10, Excellent, (1,687 reviews)
"Location was great"
United States
Pamela
The price is £247
includes taxes & fees
19 Jul - 20 Jul
Sheraton Grand Chicago Riverwalk

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.6 mi from Woodlawn
9.0 out of 10, Wonderful, (3,435 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is £206
includes taxes & fees
5 Jul - 6 Jul
Swissotel - Chicago

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 8 mi from Woodlawn
8.8 out of 10, Excellent, (2,505 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is £164
includes taxes & fees
5 Jul - 6 Jul
DoubleTree by Hilton Chicago - Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile
3.5 star property
Streeterville, 8 mi from Woodlawn
9.4 out of 10, Exceptional, (415 reviews)
"Very friendly staff, nice and clean room, great location"
United States
Bjorn Holger
The price is £203
includes taxes & fees
5 Jul - 6 Jul
Hilton Grand Vacations Club Chicago Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 7.9 mi from Woodlawn
8.2 out of 10, Very good, (2,889 reviews)
"Excelent stay in Chicago with a great breakfast that is include. Awesome location and staff was very helpful."
United States
Joseph
The price is £185
includes taxes & fees
6 Jul - 7 Jul
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
7.6 mi from Woodlawn
8.6 out of 10, Excellent, (1,963 reviews)
"Beautiful hotel, amazing staff, perfect location. Will definitely make this a regular hotel to stay at while in Chicago."
United States
April
The price is £235
includes taxes & fees
6 Jul - 7 Jul
Radisson Blu Aqua Hotel Chicago

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.5 mi from Woodlawn
8.8 out of 10, Excellent, (2,232 reviews)
"Location is excellent!"
United States
Michele
The price is £249
includes taxes & fees
7 Jul - 8 Jul
Fairmont Chicago at Millennium Park

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 8 mi from Woodlawn
8.6 out of 10, Excellent, (3,295 reviews)
"Very great hotel"
United States
Allesandra
The price is £125
includes taxes & fees
5 Jul - 6 Jul
Aloft by Marriott Chicago Mag Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 8 mi from Woodlawn
8.8 out of 10, Excellent, (1,329 reviews)
"Always love the Ivy Hotel and always a good choice!"
United States
Cindy
The price is £135
includes taxes & fees
8 Jul - 9 Jul
Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 8.5 mi from Woodlawn
8.6 out of 10, Excellent, (2,502 reviews)
"Good breakfast, great view from room"
United States
Randy
The price is £169
includes taxes & fees
5 Jul - 6 Jul
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 8 mi from Woodlawn
9.0 out of 10, Wonderful, (1,006 reviews)
"All around great stay. "
United States
Nicholas
The price is £133
includes taxes & fees
5 Jul - 6 Jul
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 8.5 mi from Woodlawn
9.0 out of 10, Wonderful, (4,478 reviews)
"Great stay!"
United States
Avradita
The price is £158
includes taxes & fees
9 Jul - 10 Jul
Hilton Chicago/Magnificent Mile Suites

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 8.5 mi from Woodlawn
8.6 out of 10, Excellent, (1,951 reviews)
"Great place to stay definitely will be coming back and staying here again."
United States
Carlos
The price is £133
includes taxes & fees
5 Jul - 6 Jul
Millennium Hotel Knickerbocker Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.6 mi from Woodlawn
9.4 out of 10, Exceptional, (3,451 reviews)
"Staff was great."
United States
Marianne
The price is £198
includes taxes & fees
5 Jul - 6 Jul
Hyatt Regency Chicago

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 8.1 mi from Woodlawn
9.0 out of 10, Wonderful, (1,107 reviews)
"Great stay!"
United States
Milo
The price is £180
includes taxes & fees
19 Jul - 20 Jul
Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 8 mi from Woodlawn
9.0 out of 10, Wonderful, (1,941 reviews)
"Great location, room was beautiful and clean!"
United States
Zhe Wen
The price is £157
includes taxes & fees
5 Jul - 6 Jul
Courtyard by Marriott Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 mi from Woodlawn
7.8 out of 10, Good, (1,672 reviews)
"Enjoyed our stay"
United States
keary
The price is £109
includes taxes & fees
5 Jul - 6 Jul
The Chicago Hotel Collection - Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
3.0 star property
Streeterville, 8.2 mi from Woodlawn
8.2 out of 10, Very good, (1,005 reviews)
"5/5 would definitely stay again!"
United States
Ivan
The price is £213
includes taxes & fees
5 Jul - 6 Jul
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
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.

Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most.

Downtown Chicago

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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Woodlawn Hotel Reviews

Frequently asked questions

What are the best hotels in Woodlawn that travellers recommend?
Two of the best hotels in Woodlawn that receive consistently high recommendations from travellers are the Sophy Hyde Park and the Hyatt Place Chicago-South/University Medical Center.

The 4-star Sophy Hyde Park, with an exceptional 9.6 rating, is highly praised for its friendly and great staff, comfortable and clean rooms, and a convenient location. Guests also appreciate the comfortable beds and the great bar. It is well-situated near attractions such as 57th Street Beach, Paul H. Douglas Nature Sanctuary, and Garden of the Phoenix.

Another excellent option is the 3-star Hyatt Place Chicago-South/University Medical Center, which has an 8.8 rating. Travellers frequently comment on the friendly and helpful staff, the great location, and the fresh breakfast. The spacious and clean rooms are also a highlight, as is the excellent and easy parking. This hotel is also close to 57th Street Beach and Paul H. Douglas Nature Sanctuary.
What are the best family hotels in Woodlawn?
For family-friendly accommodation in Woodlawn, consider the Hyatt Place Chicago-South/University Medical Center or the Sophy Hyde Park.

The 3-star Hyatt Place Chicago-South/University Medical Center, with an 8.8 rating, is popular by families. It offers connecting rooms and sofa beds, and guests frequently praise the spacious and clean rooms, as well as the fresh and good breakfast. It is conveniently located near attractions such as Jackson Park and 57th Street Beach.

Another excellent option is the 4-star Sophy Hyde Park, which boasts an impressive 9.6 rating. This hotel provides amenities like free cribs and connecting rooms. Guests consistently comment on the friendly and great staff, the comfortable and clean rooms, and the convenient location close to points of interest like the Garden of the Phoenix.
What are the top pet-friendly hotels in Woodlawn?
For top pet-friendly hotels in Woodlawn, consider the Sophy Hyde Park or the Hyatt Place Chicago-South/University Medical Center.

The 4-star Sophy Hyde Park, with an outstanding 9.6 rating, welcomes dogs and other pets. Guests frequently praise the friendly and great staff, comfortable and clean rooms, and the convenient and great location. It is also close to several lovely green spaces, including Jackson Park and the Paul H. Douglas Nature Sanctuary.

Another excellent option is the 3-star Hyatt Place Chicago-South/University Medical Center, rated 8.8. This hotel also permits pets and specifically dogs, though a cleaning fee may apply. Travellers often highlight the friendly and helpful staff, the great location, and the fresh and good breakfast. It is also conveniently located near Jackson Park and the 57th Street Beach.
What are the best budget hotels in Woodlawn?
For a highly-rated budget hotel in Woodlawn, consider the Hyatt Place Chicago-South/University Medical Center.

This 3-star hotel, with an 8.8 rating, is much-loved by guests for its friendly and helpful staff, as well as its good location. Guests particularly appreciate the fresh and tasty breakfast, the spacious and clean rooms, and the excellent, easy parking facilities. The hotel offers complimentary WiFi, free cribs, and a free area shuttle for added convenience. It is also well-situated for exploring nearby attractions such as the Barack Obama Residence, which is just 0.9 km away, and the Hyde Park Art Centre, located 0.4 km from the hotel.
What are the most romantic hotels in Woodlawn for couples?
For a romantic stay in Woodlawn, the Sophy Hyde Park is an excellent choice for couples.

This 4-star hotel, with an impressive 9.6 rating, is highly praised by guests for its comfortable and clean rooms, along with its friendly and great staff. The hotel offers complimentary toiletries, free WiFi, and free cribs if needed. Couples will appreciate the dedicated couples dining option, great for a special evening. Its convenient location places you within easy reach of local attractions such as the Hyde Park Art Centre, just 0.6 km away, and the historic Robie House, 1.1 km away. The on-site bar is also frequently mentioned by guests as being great.
What are the best hotels in Woodlawn near Garden of the Phoenix?
For a stay in Woodlawn near the Garden of the Phoenix, the University of Chicago Condo-Upgraded and Spacious w/Parking is a highly-rated option.

This property, with an exceptional 10.0 rating, is conveniently located just 1.6 km from the Garden of the Phoenix. It offers families a comfortable stay with a kitchen, a patio, and an outdoor play area for children. Onsite parking is also available, adding to the convenience for guests.
When is the best time to go to Woodlawn?
The best time to visit Woodlawn, Illinois, is during the spring (late April to early June) and autumn (September to October) months.

During these periods, the weather is generally mild and pleasant, with comfortable temperatures ideal for outdoor activities. Spring brings blooming wildflowers and lush greenery to the surrounding natural areas, while autumn offers spectacular displays of fall foliage. These seasons avoid the intense heat and humidity of summer and the cold, snowy conditions of winter.

Couples looking for a peaceful escape will appreciate the serene beauty of Woodlawn in spring and autumn. You can enjoy strolls through the nearby Wayne Fitzgerrell State Park or explore the scenic trails around Rend Lake without the discomfort of extreme weather. The cooler temperatures also make wildlife viewing more enjoyable.

Families will find these times superb for outdoor adventures. The mild weather is great for fishing, boating, or picnicking at Rend Lake.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Woodlawn.
How can I save on a Woodlawn hotel booking with Expedia?
Members always get our best prices. Find our best Woodlawn hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Woodlawn hotel?
Hotel prices in Woodlawn often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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