Hotels in Woodlawn, Chicago

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Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.6 out of 10, (56 reviews)
"Kindest staff in the whole city | cleanliness improving | the amenities and cleanliness do not justify the price, could definitely find better for cheaper in Chicago BUT they are improving. "
United States
Savon
Best Motel By OYO Chicago I-90

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 12.6 km from Woodlawn
9.4 out of 10, Exceptional, (2,402 reviews)
"Great stay! I will stay here again on my next trip back this summer!"
United States
Letisha
The price is CA $205
CA $287 total
includes taxes & fees
Mar 30 - Mar 31
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,697 reviews)
"Amazing place to stay!"
United States
Nia
The price is CA $179
CA $250 total
includes taxes & fees
Apr 1 - Apr 2
Hilton Chicago

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very good, (1,745 reviews)
"Loved this hotel, i will be back"
United States
Shari
The price is CA $174
CA $205 total
includes taxes & fees
Mar 22 - Mar 23
The Wade

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.1 km from Woodlawn
8.6 out of 10, Excellent, (2,087 reviews)
"Great location and nicely maintained rooms "
United States
Brianna
The price is CA $232
CA $321 total
includes taxes & fees
Mar 24 - Mar 25
Fairmont Chicago at Millennium Park

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,227 reviews)
"Helpful staff, great location with views, restaurant and bar on-site"
United States
Natalie
The price is CA $196
CA $279 total
includes taxes & fees
Mar 29 - Mar 30
Swissotel - Chicago

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.3 km from Woodlawn
9.6 out of 10, Exceptional, (3,793 reviews)
"Amazing hotel-- Loved staying here."
United States
Maureen
The price is CA $210
CA $247 total
includes taxes & fees
Mar 24 - Mar 25
L7 Chicago by LOTTE

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,029 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is CA $130
CA $152 total
includes taxes & fees
Mar 23 - Mar 24
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (9,978 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is CA $143
CA $168 total
includes taxes & fees
Apr 1 - Apr 2
Congress Plaza Hotel

Pendry Chicago

Pendry Chicago
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.2 out of 10, Wonderful, (1,122 reviews)
"Great location, clean and very nice restaurant and bar. "
United States
karina
The price is CA $261
CA $362 total
includes taxes & fees
Apr 12 - Apr 13
Pendry Chicago

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 11.7 km from Woodlawn
9.2 out of 10, Wonderful, (2,237 reviews)
"Room was great- fantastic location- so easy to get everywhere!"
United States
Victoria
The price is CA $156
CA $226 total
includes taxes & fees
Apr 5 - Apr 6
Silversmith Hotel Chicago Downtown

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (1,921 reviews)
"Hotel was really nice"
United States
LaCarr
The price is CA $156
CA $184 total
includes taxes & fees
Apr 5 - Apr 6
Hilton Garden Inn Chicago Downtown South Loop

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 11.7 km from Woodlawn
8.6 out of 10, Excellent, (2,332 reviews)
"We had a great stay and the staff are very friendly and accommodating. "
United States
Krista
The price is CA $185
CA $251 total
includes taxes & fees
Apr 5 - Apr 6
Palmer House a Hilton Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.8 out of 10, Excellent, (1,175 reviews)
"Clean friendly staff love the decor "
United States
Kiasha
The price is CA $147
CA $173 total
includes taxes & fees
Mar 24 - Mar 25
Ivy Boutique Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,147 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is CA $148
CA $174 total
includes taxes & fees
Mar 29 - Mar 30
Aloft Chicago Mag Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.2 km from Woodlawn
8.6 out of 10, Excellent, (1,867 reviews)
"Overall a great stay."
United States
Joshua
The price is CA $203
CA $274 total
includes taxes & fees
Mar 29 - Mar 30
Radisson Blu Aqua Hotel Chicago

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,033 reviews)
"Great hotel in a great location."
United States
Ben
The price is CA $129
CA $152 total
includes taxes & fees
Mar 23 - Mar 24
Central Loop Hotel

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (2,125 reviews)
"Great stay!"
United States
Hannah
The price is CA $130
CA $152 total
includes taxes & fees
Mar 23 - Mar 24
Club Quarters Hotel Wacker at Michigan, Chicago

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 11.7 km from Woodlawn
9.0 out of 10, Wonderful, (2,416 reviews)
"this location is safe and convenient-would book here again."
United States
eduardo
The price is CA $192
CA $260 total
includes taxes & fees
Mar 27 - Mar 28
Hyatt Centric The Loop Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 14.4 km from Woodlawn
8.2 out of 10, Very good, (1,316 reviews)
"Very beautiful place to stay"
United States
angie
The price is CA $184
CA $216 total
includes taxes & fees
Mar 22 - Mar 23
The Chicago Hotel Collection Ambassador Gold Coast
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 and neighborhoods 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

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

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

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.

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

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?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Woodlawn hotel for you.
How can I save on a Woodlawn hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Woodlawn hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to 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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