Find hotels in Woodlawn, Chicago from SAR 286

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

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, (64 reviews)
"Parking was easy. Just a sign in"
United States
David
The price is SAR 230
SAR 286 total
includes taxes & fees
2 Jun - 3 Jun
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, (2,482 reviews)
"Great place to stay "
United States
Mark
The price is SAR 711
SAR 975 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2,428 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is SAR 555
SAR 771 total
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (4,034 reviews)
"It was great property, amazing location and the breakfast was fantastic. "
United States
Nichole
The price is SAR 505
SAR 706 total
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago

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, (1,976 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is SAR 491
SAR 584 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,296 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is SAR 743
SAR 1,016 total
includes taxes & fees
27 May - 28 May
Swissotel - 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, (2,243 reviews)
"This was a great hotel. The staff and accommodations were terrific. I really enjoyed my stay "
United States
Alex
The price is SAR 447
SAR 646 total
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,156 reviews)
"Excellent location, very clean room and friendly staff"
United States
Alejandra
The price is SAR 596
SAR 709 total
includes taxes & fees
26 May - 27 May
River Hotel

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, (1,056 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is SAR 521
SAR 730 total
includes taxes & fees
10 May - 11 May
Staypineapple, An Iconic Hotel, The Loop

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, (3,412 reviews)
"Enjoyed our 5 night stay immensely"
United States
Marilyn
The price is SAR 680
SAR 928 total
includes taxes & fees
10 May - 11 May
The Royal Sonesta Chicago Downtown

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,102 reviews)
"Great breakfast and staff. "
United States
Kelly
The price is SAR 671
SAR 912 total
includes taxes & fees
25 May - 26 May
Arlo Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3,681 reviews)
"Loved staying at this hotel"
United States
Kimberly Marie
The price is SAR 700
SAR 943 total
includes taxes & fees
10 May - 11 May
LondonHouse 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, (2,770 reviews)
"Clean room and great location "
United States
Diana
The price is SAR 596
SAR 819 total
includes taxes & fees
25 May - 26 May
Hilton Chicago

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 13.1 km from Woodlawn
8.4 out of 10, Very Good, (580 reviews)
"Great location great staff great hotel!"
United States
Refak
The price is SAR 334
SAR 392 total
includes taxes & fees
25 May - 26 May
FOUND Hotel Chicago River North

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, (2,141 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is SAR 646
SAR 902 total
includes taxes & fees
8 May - 9 May
Fairmont Chicago at Millennium Park

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very Good, (10,134 reviews)
"Great stay"
United States
Matthew
The price is SAR 470
SAR 559 total
includes taxes & fees
8 May - 9 May
Congress Plaza Hotel

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very Good, (2,939 reviews)
"Great stay"
United States
Agnes Nmabila
The price is SAR 350
SAR 483 total
includes taxes & fees
25 May - 26 May
Freehand Chicago

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, (2,234 reviews)
"Perfect location great room for the price "
United States
Lisa
The price is SAR 505
SAR 601 total
includes taxes & fees
26 May - 27 May
Club Quarters Hotel Wacker at Michigan, Chicago

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,625 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is SAR 821
SAR 1,110 total
includes taxes & fees
9 May - 10 May
Sheraton Grand Chicago Riverwalk

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 12.7 km from Woodlawn
9.2 out of 10, Wonderful, (3,034 reviews)
"Great stay all around "
United States
Logan
The price is SAR 746
SAR 1,019 total
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG
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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

Find out more about Woodlawn

Top reasons to visit Woodlawn

  • Cultural Vibrancy: Explore Woodlawn's rich art scene and local history, providing a unique cultural experience.
  • Outdoor Activities: Enjoy family-friendly outings at urban parks and the Woodlawn Sports Complex.
  • Scenic Neighborhoods: Stroll through charming streets and experience the friendly atmosphere of the local community.
  • Diverse Accommodations: Choose from a variety of lodging options, including luxury hotels and cozy bed and breakfasts.
  • Convenient Shopping: Engage in shopping adventures at nearby retail locations, perfect for souvenirs and local goods.

Find great hotels near Woodlawn

Discover a variety of accommodations in Woodlawn, Chicago, perfect for every type of traveler. From luxurious hotels to charming bed and breakfasts, you'll find options that cater to business needs, pet-friendly amenities, and an inclusive atmosphere for LGBTQIA visitors. Whether you're seeking the best hotel experiences or a comfortable Hyatt stay, Woodlawn has something to suit your vacation desires.

  • Congress Plaza Hotel: Nestled within the vibrant shopping district, Congress Plaza Hotel is a 3.5-star property that caters to both business travelers and shopping enthusiasts. Located only 11.3km from Woodlawn, this hotel boasts a historic charm with modern amenities. Guests can enjoy spacious rooms equipped with complimentary Wi-Fi, a fitness center for workouts, and an on-site restaurant serving delicious meals. Its prime location makes it easy to explore local shops and attractions, making it an ideal choice for those seeking a blend of business and leisure.
  • Hyatt Regency Chicago: Situated 12.9km from Woodlawn in the bustling city center, Hyatt Regency Chicago is a sophisticated 4-star hotel that welcomes all travelers, including the LGBTQIA community. This urban retreat features sleek accommodations with stunning city views, a state-of-the-art fitness center, and diverse dining options. With its central location, guests have easy access to Chicago's iconic landmarks, shopping, and dining experiences. The hotel’s commitment to inclusivity and exceptional service ensures a memorable stay for everyone.
  • Best Western Grant Park Hotel: Just 9.7km from Woodlawn, Best Western Grant Park Hotel is an excellent choice for families and shoppers alike. This welcoming property offers family-friendly amenities, including complimentary cribs and safety features for children. Guests can unwind in comfortable rooms while enjoying convenient access to nearby shopping venues. With its focus on family comfort and convenience, this hotel is perfect for those looking to explore the area while keeping the little ones entertained.

Where to stay near Woodlawn

Woodlawn, Chicago, offers a unique blend of cultural experiences and family-friendly activities. Visitors can explore the vibrant local art scene, enjoy recreational parks, and indulge in cozy dining spots. Nearby neighborhoods provide a mix of urban charm and friendly atmospheres, perfect for both relaxation and adventure. Whether you're strolling through scenic streets or engaging with the community, Woodlawn promises an unforgettable vacation experience for all types of travelers.

  • Chicago: A vibrant metropolis, Chicago offers a diverse urban experience with a mix of culture, entertainment, and recreational activities. As the third-largest city in the U.S., it boasts a rich history and iconic architecture. Visitors can explore renowned shopping districts, enjoy thrilling sports events at local stadiums, and unwind in expansive urban parks. The city's festive atmosphere peaks during the summer months, making it an ideal time for family outings and outdoor adventures.
  • Hyde Park: Located just 1.6km from Woodlawn, Hyde Park is a culturally rich neighborhood known for its beautiful tree-lined streets and the prestigious University of Chicago. This area is perfect for families and culture enthusiasts, with attractions like historic colleges and lush urban parks. Hyde Park features a variety of shopping options and entertainment venues, making it a great spot for leisurely strolls and educational experiences. The neighborhood's vibrant community spirit shines through in its numerous cultural events throughout the year.
  • Washington Park: Also situated 1.6km away from Woodlawn, Washington Park is a family-friendly neighborhood that combines culture and outdoor experiences. The area is known for its historic college, beautiful parks, and sports facilities, making it ideal for both relaxation and recreation. Visitors can enjoy educational attractions, shopping areas, and various entertainment options, all within a close-knit community atmosphere. Washington Park is particularly lively during the warmer months, attracting visitors who seek both leisure and cultural enrichment.

Things to do near Woodlawn

Woodlawn, Chicago, offers a vibrant mix of culture and outdoor experiences perfect for family vacations. Visitors can explore the area, enjoy family outings, and engage in activities at the Woodlawn Sports Complex. With a variety of educational opportunities and arena entertainment facilities nearby, Woodlawn provides an ideal backdrop for dream weddings and shopping adventures, ensuring a memorable trip for all.

Shopping

For a great shopping experience in Woodlawn, visit Chicago Place Mall and Shops at North Bridge, both 12.9km away, offering a mix of family and business vibes. Don't miss the Maxwell Street Market, located just 9.7km away, for a lively public market atmosphere.

Recreation

Experience the excitement at Soldier Field, just 9.7km away, where you can catch a game or event amidst vibrant sports energy. For a more tranquil escape, visit the Northerly Island Natural Area, located 8.0km away, perfect for relaxation and rejuvenation in nature's embrace.

Adventure

Explore the scenic Salt Creek Trail, a perfect spot for hiking located 19.3km from Woodlawn, offering breathtaking views and outdoor adventure vibes. For water fun, visit Rainbow Falls Waterpark, 40.2km away, or Deep River Water Park, 46.7km away, both featuring thrilling rides and family-friendly entertainment.

Nightlife

Experience the vibrant nightlife in Woodlawn with a visit to the Chicago Theatre for a romantic show, or catch a family-friendly film at Film Row Cinema. For a fun adventure, explore Amazing Chicago's Funhouse Maze, perfect for thrill-seekers looking for excitement.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Woodlawn

For a budget-friendly visit to Woodlawn, consider traveling during the off-peak months of December to February when lodging prices are lower. Book your stay on a Monday for the best rates, avoiding the more expensive Saturday nights. Use Expedia to find great hotel deals by filtering options from lowest to highest price, and consider bundling your hotel with flights and activities for additional savings. Explore free attractions in the area and utilize public transportation to cut down on travel costs.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Woodlawn are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Woodlawn is Monday. The most expensive day to stay around Woodlawn is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. To discover the best prices and deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Woodlawn hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Woodlawn

Woodlawn, Chicago, is perfect for cultural, family, and outdoor vacations, featuring urban parks, historic houses, and nearby beaches. Visitors can explore attractions like Woodlawn Park and the local hospital, offering a rich city experience for travelers seeking culture and family-friendly activities. Enjoy the unique blend of history and nature that Woodlawn has to offer during your visit.

  • McCormick Place: Located 8.0km from Woodlawn, McCormick Place is the largest convention center in North America. It hosts a variety of events, from trade shows to conferences, offering a vibrant atmosphere filled with business energy and networking opportunities.
  • University of Chicago: Just 1.4km away, this historic university is renowned for its stunning Gothic architecture and rich cultural heritage. Explore its beautiful campus and take in the intellectual atmosphere that has produced numerous Nobel laureates.
  • Chicago Museum of Science and Industry: Situated 3.2km from Woodlawn, this family-friendly museum features interactive exhibits that engage visitors of all ages. Discover the wonders of science and technology in a space that inspires curiosity and learning.

Best time to go to Woodlawn

The best time to visit Woodlawn is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

The nearest major airports for your trip to Woodlawn

Traveling to Woodlawn, Chicago, is convenient with access to two major airports. Chicago O'Hare International Airport (ORD) is approximately 32.2km away, with nearby accommodations such as the 4.5-star Loews Chicago O'Hare Hotel, located 3.2km from the airport, and the 4-star Hilton Chicago O'Hare Airport, just 161m away. Midway International Airport (MDW) is closer, at about 11.3km from Woodlawn, with luxurious options like the 5-star Nobu Hotel Chicago, 12.9km away, and The Langham, Chicago, 14.5km away. For those flying into Chicago Executive Airport (PWK), situated 212.9km from Woodlawn, notable hotels include the 4.5-star Deer Path Inn and the 4-star Embassy Suites by Hilton Chicago North Shore Deerfield.

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Woodlawn?
Woodlawn is a neighborhood that travelers like for its beaches, restaurants, and gardens. Looking for sights you might find in a travel guide about Woodlawn? Consider a visit to Lake Michigan while you're in the neighborhood.
Where is the best place to stay in Woodlawn?
Based on Expedia customer reviews, Best Motel By OYO Chicago I-90 is the highest ranked property in Woodlawn. This property offers free valet parking and flat-screen TVs.
How many hotels will I be able to find in the Woodlawn area?
If you're searching for places to stay in Chicago, Expedia has something to meet your needs with 47 Woodlawn hotels and other accommodations to choose from.
If I need to cancel my hotel reservation in Woodlawn, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Enter your dates, click on "Search", then use the "fully refundable" filter to view top deals in Woodlawn.
Where can I learn more about changing or cancelling my trip to Woodlawn?
To access more information about updating your trip to Woodlawn or cancelling it, go to https://www.expedia.com/service/.
What can I see and do in this Chicago neighborhood?
Spend some time exploring the great outdoors at Lake Michigan, Jackson Park, and Bob-O-Link Meadow. Lorado Taft's Midway Studios and Jackson Park Driving Range are also a couple of places to visit in the neighborhood. Oak Woods Cemetery, Stony Island Arts Bank, and Rockefeller Memorial Chapel are just a few of the places to visit in and around Woodlawn. While you're out sightseeing in Chicago, be sure to visit other sights like Oriental Institute Museum or Bond Chapel.
How can I get around Woodlawn and the greater Chicago area?
Looking for a quick way to explore more of the city? Catch a ride on metro transit at Cottage Grove Station and King Drive Station. To venture out of town, take a train from Chicago 63rd Street Station.