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Hotels in Woodlawn, Chicago

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Our top choices for Woodlawn hotels

1. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.4 out of 10, (164 reviews)
"The motel smell like rats. And i stay there no more 30 minutes and chek out i pay $130"
United States
Rifki
The price is CA $117
CA $138 total
includes taxes & fees
Nov 16 - Nov 17
Best Motel By OYO Chicago I-90

2. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 11.1 km from Woodlawn
9.6 out of 10, Exceptional, (1,210 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is CA $159
CA $189 total
includes taxes & fees
Dec 10 - Dec 11
Hilton Vacation Club Hotel Blake Chicago

3. 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, (2,765 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is CA $159
CA $238 total
includes taxes & fees
Dec 15 - Dec 16
Sable at Navy Pier Chicago, Curio Collection by Hilton

4. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 10.3 km from Woodlawn
8.2 out of 10, Very good, (2,754 reviews)
"Nice location. Restaurants are just walking distance."
United States
Diojenies Alejandro
The price is CA $122
CA $145 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Grant Park Hotel

5. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 10.6 km from Woodlawn
9.0 out of 10, Wonderful, (1,003 reviews)
"Fantastic location and facility. Comfortable bed and nice shower! Perfect hotel for the Bears Game!"
United States
Taso
The price is CA $160
CA $215 total
includes taxes & fees
Dec 7 - Dec 8
Le Méridien Essex Chicago

6. 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, (2,207 reviews)
"We liked that it was dog friendly."
United States
Jacquelyn
The price is CA $138
CA $162 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Chicago Downtown South Loop

7. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2,588 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is CA $138
CA $164 total
includes taxes & fees
Dec 7 - Dec 8
DoubleTree by Hilton Chicago - Magnificent Mile

8. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (1,720 reviews)
"Clean room, very helpful staff, centrally located."
United States
Katherine
The price is CA $156
CA $186 total
includes taxes & fees
Dec 14 - Dec 15
Cambria Hotel Chicago Loop - Theatre District

9. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1,930 reviews)
"Hotel is great for the price."
United States
alex
The price is CA $121
CA $144 total
includes taxes & fees
Dec 7 - Dec 8
ACME Hotel Chicago, Outset Collection by Hilton

10. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.6 km from Woodlawn
9.0 out of 10, Wonderful, (5,070 reviews)
"Great place to stay"
United States
Melissa
The price is CA $146
CA $173 total
includes taxes & fees
Dec 10 - Dec 11
Hilton Chicago/Magnificent Mile Suites

11. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.6 km from Woodlawn
8.4 out of 10, Very good, (3,971 reviews)
"This hotel was amazing. The staff are super nice and welcoming and it’s in a great location. Would stay again!"
United States
Luna
The price is CA $115
CA $137 total
includes taxes & fees
Dec 7 - Dec 8
The Whitehall Hotel, BW Premier Collection

12. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (2,537 reviews)
"Location was great, staff was friendly and we had everything we needed for our trip."
United States
Chad
The price is CA $154
CA $181 total
includes taxes & fees
Nov 23 - Nov 24
Homewood Suites by Hilton Chicago Downtown South Loop

13. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.8 out of 10, Good, (2,977 reviews)
"Great place to stay for a weekend. Honestly right in the heart of the city for a great price."
United States
Melanie
The price is CA $148
CA $175 total
includes taxes & fees
Dec 9 - Dec 10
Travelodge by Wyndham Downtown Chicago

14. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 12.7 km from Woodlawn
8.4 out of 10, Very good, (3,022 reviews)
"Great stay!"
United States
Serge
The price is CA $171
CA $245 total
includes taxes & fees
Dec 14 - Dec 15
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

15. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,588 reviews)
"Great hotel"
United States
Daniel Michael
The price is CA $179
CA $263 total
includes taxes & fees
Dec 13 - Dec 14
Swissotel - Chicago

16. River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,617 reviews)
"Great location and lovely staff"
United States
Jillian
The price is CA $141
CA $168 total
includes taxes & fees
Dec 15 - Dec 16
River Hotel

17. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,350 reviews)
"Great stay !"
United States
Marianna
The price is CA $139
CA $165 total
includes taxes & fees
Dec 10 - Dec 11
Central Loop Hotel

18. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (2,828 reviews)
"Wonderful stay!"
United States
Dejai
The price is CA $164
CA $195 total
includes taxes & fees
Nov 22 - Nov 23
Crowne Plaza Chicago West Loop by IHG

19. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
12.7 km from Woodlawn
9.0 out of 10, Wonderful, (1,310 reviews)
"Loved the continental breakfast and how close different bars and restaurants were at :)"
United States
Carole
The price is CA $199
CA $236 total
includes taxes & fees
Nov 25 - Nov 26
Hyatt House Chicago/West Loop-Fulton Market

20. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (3,550 reviews)
"Enjoyed my stay will book again!"
United States
Jordan
The price is CA $193
CA $271 total
includes taxes & fees
Nov 22 - Nov 23
Hilton 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.

Compare popular hotels in Woodlawn

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A room with large windows, a wooden floor, and a built-in air conditioning unit.
Best Motel By OYO Chicago I-90
2.5 star property
3.4
164 reviews
View
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago
4.0 star property
9.6
Exceptional
1,210 reviews
View
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
9.4
Exceptional
3,896 reviews
View
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
L7 CHICAGO by LOTTE HOTELS
4.5 star property
9.6
Exceptional
5,246 reviews
View
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
Hyatt Regency Chicago
4.0 star property
9.4
Exceptional
3,502 reviews
View

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 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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