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
3.8 out of 10, (60 reviews)
"Parking"
United States
Sydney
The price is CA $78
CA $97 total
includes taxes & fees
May 6 - May 7
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, (2,441 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is CA $285
CA $382 total
includes taxes & fees
Apr 13 - Apr 14
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,734 reviews)
"Great hotel "
United States
Marina
The price is CA $180
CA $250 total
includes taxes & fees
Apr 28 - Apr 29
Hotel Riu Plaza Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,064 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is CA $165
CA $193 total
includes taxes & fees
Apr 26 - Apr 27
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, (10,050 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is CA $151
CA $177 total
includes taxes & fees
Apr 16 - Apr 17
Congress Plaza Hotel

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,725 reviews)
"We love staying here "
United States
Carrie
The price is CA $278
CA $367 total
includes taxes & fees
Apr 10 - Apr 11
Hilton 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, (3,868 reviews)
"Loved the stay here !"
United States
Alisha
The price is CA $172
CA $201 total
includes taxes & fees
Apr 8 - Apr 9
L7 Chicago by LOTTE

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3,373 reviews)
"I loved my stay"
United States
Janet
The price is CA $212
CA $293 total
includes taxes & fees
Apr 30 - May 1
The Royal Sonesta Chicago Downtown

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (2,106 reviews)
"lovely hotel "
United States
alyvia
The price is CA $267
CA $362 total
includes taxes & fees
Apr 10 - Apr 11
Fairmont Chicago at Millennium Park

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,378 reviews)
"Great stay"
United States
Ashley
The price is CA $179
CA $210 total
includes taxes & fees
Apr 7 - Apr 8
Eurostars Magnificent Mile

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,058 reviews)
"For the price, it was a very nice a room and location. "
United States
Anna
The price is CA $129
CA $151 total
includes taxes & fees
Apr 8 - Apr 9
Central Loop 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, (3,167 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is CA $169
CA $198 total
includes taxes & fees
Apr 12 - Apr 13
Aloft Chicago Mag Mile

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, (1,949 reviews)
"Hotel was really nice"
United States
LaCarr
The price is CA $191
CA $224 total
includes taxes & fees
Apr 26 - Apr 27
Hilton Garden Inn Chicago Downtown South Loop

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, (2,153 reviews)
"Great stay!"
United States
Hannah
The price is CA $146
CA $171 total
includes taxes & fees
Apr 26 - Apr 27
Club Quarters Hotel Wacker at Michigan, Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 11.9 km from Woodlawn
9.4 out of 10, Exceptional, (1,034 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is CA $185
CA $259 total
includes taxes & fees
Apr 26 - Apr 27
Staypineapple, An Iconic Hotel, The 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, (2,359 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is CA $300
CA $387 total
includes taxes & fees
May 7 - May 8
Palmer House a Hilton Hotel

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 13.1 km from Woodlawn
8.6 out of 10, Excellent, (531 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is CA $108
CA $127 total
includes taxes & fees
Apr 14 - Apr 15
FOUND Hotel Chicago River North

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, (2,243 reviews)
"Great stay!"
United States
Jessica
The price is CA $170
CA $242 total
includes taxes & fees
Apr 27 - Apr 28
Silversmith Hotel Chicago Downtown

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, (1,359 reviews)
"Very beautiful place to stay"
United States
angie
The price is CA $155
CA $182 total
includes taxes & fees
Apr 20 - Apr 21
The Chicago Hotel Collection Ambassador Gold Coast

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,068 reviews)
"Great location and very clean hotel with nice staff. "
United States
Carrie
The price is CA $177
CA $248 total
includes taxes & fees
Apr 7 - Apr 8
Arlo 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.

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.

O'Hare

Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

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.

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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