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, (55 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, (2,394 reviews)
"Great location, friendly staff. "
United States
Brian
The price is CA $196
CA $277 total
includes taxes & fees
Mar 24 - Mar 25
Sable at Navy Pier Chicago, Curio Collection by Hilton

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,216 reviews)
"Helpful staff, great location with views, restaurant and bar on-site"
United States
Natalie
The price is CA $166
CA $243 total
includes taxes & fees
Mar 30 - Mar 31
Swissotel - Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,675 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, (1,718 reviews)
"Walking distance to most of what we wanted to see. "
United States
Tabitha
The price is CA $177
CA $208 total
includes taxes & fees
Mar 31 - Apr 1
The Wade

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (9,922 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is CA $132
CA $155 total
includes taxes & fees
Apr 1 - Apr 2
Congress Plaza Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,527 reviews)
"Great location ans staff was amazing!!"
United States
Bianca
The price is CA $180
CA $250 total
includes taxes & fees
Mar 30 - Mar 31
Hotel Riu Plaza Chicago

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 10.6 km from Woodlawn
8.8 out of 10, Excellent, (1,003 reviews)
"Clean rooms, lots to check out near by"
United States
Kassia
The price is CA $107
CA $150 total
includes taxes & fees
Apr 5 - Apr 6
Le Méridien Essex 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, (1,017 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is CA $181
CA $253 total
includes taxes & fees
Mar 29 - Mar 30
Staypineapple, An Iconic Hotel, The Loop

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, (1,902 reviews)
"Staff was friendly, valet parking is quick and the attached restaurant is very good."
United States
Codi
The price is CA $162
CA $190 total
includes taxes & fees
Apr 13 - Apr 14
Hilton Garden Inn Chicago Downtown South Loop

Pendry Chicago

Pendry Chicago
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.4 out of 10, Exceptional, (1,129 reviews)
"Great location, clean and very nice restaurant and bar. "
United States
karina
The price is CA $259
CA $360 total
includes taxes & fees
Apr 12 - Apr 13
Pendry 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, (3,765 reviews)
"Amazing hotel-- Loved staying here."
United States
Maureen
The price is CA $209
CA $245 total
includes taxes & fees
Mar 17 - Mar 18
L7 Chicago by LOTTE

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,014 reviews)
"Nice little getaway, I really enjoyed the staff "
United States
Joshua
The price is CA $195
CA $270 total
includes taxes & fees
Mar 29 - Mar 30
Arlo Chicago

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, (3,909 reviews)
"Great hotel great location. "
United States
Michael
The price is CA $142
CA $166 total
includes taxes & fees
Mar 23 - Mar 24
Hilton Chicago/Magnificent Mile Suites

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.2 out of 10, Wonderful, (1,407 reviews)
"Check in was quick and easy, room was clean and spacious "
United States
Quinton
The price is CA $214
CA $290 total
includes taxes & fees
Mar 25 - Mar 26
Sports Illustrated Resorts 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, (2,235 reviews)
"Personable staff, nice clean place throughout. "
United States
Michael
The price is CA $156
CA $225 total
includes taxes & fees
Apr 5 - Apr 6
Silversmith Hotel Chicago Downtown

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,305 reviews)
"Greatest hotel "
United States
Solomon
The price is CA $194
CA $227 total
includes taxes & fees
Mar 25 - Mar 26
Eurostars Magnificent Mile

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, (2,400 reviews)
"Clean with great views. "
United States
Kent
The price is CA $192
CA $255 total
includes taxes & fees
Mar 20 - Mar 21
Hyatt Centric The Loop Chicago

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.8 out of 10, Excellent, (1,158 reviews)
"Great location"
United States
Tony
The price is CA $146
CA $171 total
includes taxes & fees
Mar 22 - Mar 23
Ivy Boutique Hotel

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, (2,071 reviews)
"amazing stay 10/10 would recommend "
United States
laila
The price is CA $231
CA $319 total
includes taxes & fees
Mar 29 - Mar 30
Fairmont Chicago at Millennium Park
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?
Sophy Hyde Park stands out as a premier option in Woodlawn, boasting an outstanding score of 9.6. This elegantly designed hotel, located in a historical district, offers not only modern amenities like complimentary WiFi and premium bedding but also delightful touches such as bathrobes and a terrace for relaxing evenings. Couples will appreciate the intimate dining experience, superb for a romantic getaway.

For families, the Hyatt Place Chicago-South/University Medical Center is an excellent choice with a traveller rating of 8.8. It features a complimentary buffet breakfast that will please even the pickiest eaters, while the indoor pool provides hours of fun for the kids. The hotel is incredibly accommodating, offering free cribs and a kid-friendly dining menu, ensuring a comfortable stay for families looking for quality and convenience.
What are the best family hotels in Woodlawn?
Sophy Hyde Park is a fantastic family-friendly hotel located in Chicago's vibrant Woodlawn neighbourhood, boasting an impressive traveller review score of 9.6. This hotel offers amenities that cater to families, including free cribs and connecting rooms, ensuring that parents and children can enjoy their space and stay comfortably together.

Another excellent choice is the Hyatt Place Chicago-South/University Medical Center, which has earned an excellent review score of 8.8. This property goes above and beyond for families with features like a child-friendly window design, free meals for kids, and spacious rooms that include sofa beds and connecting rooms. Guests appreciate the complimentary buffet breakfast, which makes mornings a breeze for busy families.
What hotels in Woodlawn offer free breakfast?
Hyatt Place Chicago-South/University Medical Center is a fantastic option for travellers looking for a comfortable stay in Woodlawn. This hotel stands out with its complimentary breakfast, ensuring you and your family start your day off right. Guests appreciate the inclusive setting and the convenience of amenities like an indoor pool, superb for relaxing after a day of exploring the city.
What are the best budget hotels in Woodlawn?
Hyatt Place Chicago-South/University Medical Center is an excellent budget-friendly option in Woodlawn, boasting a traveller review score of 8.8. Families will appreciate the spacious rooms equipped with convenient amenities like a sofa bed and cribs for the little ones, ensuring everyone has a comfy place to rest.
What are the most romantic hotels in Woodlawn for couples?
For a romantic getaway, Sophy Hyde Park in Chicago is a great choice, boasting an impressive review score of 9.6. This charming hotel offers a warm and inclusive setting, allowing couples to enjoy their time together in comfort and style.
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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