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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
3.6 out of 10, (145 reviews)
"A/c working, friendly staff, free parking but messy sheets and a baby mouse in the room"
United States
Saul
The price is SAR 309
SAR 362 total
includes taxes & fees
19 Oct - 20 Oct
Best Motel By OYO Chicago I-90

2. 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, (2,725 reviews)
"Amazing place to stay"
United States
Shanequa
The price is SAR 1,015
SAR 1,336 total
includes taxes & fees
29 Oct - 30 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton

3. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (3,306 reviews)
"Great stay!"
United States
Alan
The price is SAR 641
SAR 873 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Chicago

4. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,503 reviews)
"Really great stay and experience"
United States
Whitney
The price is SAR 1,186
SAR 1,544 total
includes taxes & fees
25 Oct - 26 Oct
Hyatt Regency Chicago

5. 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, (2,491 reviews)
"Great overall stay within walking distance of so much."
United States
Cecilia
The price is SAR 1,045
SAR 1,242 total
includes taxes & fees
12 Oct - 13 Oct
Homewood Suites by Hilton Chicago Downtown South Loop

6. Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop
3.5 star property
Theatre District, 11.8 km from Woodlawn
9.4 out of 10, Exceptional, (1,010 reviews)
"We enjoyed our stay."
United States
Karla
The price is SAR 987
SAR 1,174 total
includes taxes & fees
24 Oct - 25 Oct
Residence Inn Chicago Downtown/Loop

7. 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, (2,169 reviews)
"Great place to stay at"
United States
Aran
The price is SAR 935
SAR 1,112 total
includes taxes & fees
27 Oct - 28 Oct
Hilton Garden Inn Chicago Downtown South Loop

8. 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, (4,907 reviews)
"Lovely hotel in a great location with a great staff"
United States
Emily
The price is SAR 1,077
SAR 1,280 total
includes taxes & fees
25 Oct - 26 Oct
L7 Chicago by LOTTE

9. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,352 reviews)
"I really liked the location of the hotel."
United States
Carmina
The price is SAR 1,038
SAR 1,234 total
includes taxes & fees
15 Oct - 16 Oct
Aloft by Marriott Chicago Mag Mile

10. 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, (1,245 reviews)
"The room was clean and the building was nostalgic."
United States
John
The price is SAR 1,186
SAR 1,410 total
includes taxes & fees
14 Oct - 15 Oct
Hilton Vacation Club Hotel Blake Chicago

11. Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,843 reviews)
"Beautiful views, good location!"
United States
John
The price is SAR 1,235
SAR 1,603 total
includes taxes & fees
24 Oct - 25 Oct
Sheraton Grand Chicago Riverwalk

12. 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, (3,876 reviews)
"Great location! Would stay again!"
United States
Sharee
The price is SAR 951
SAR 1,242 total
includes taxes & fees
25 Oct - 26 Oct
LondonHouse Chicago, Curio Collection by Hilton

13. 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, (3,033 reviews)
"The staff was excellent so helpful and ensured our stay was enjoyable."
United States
Patricia
The price is SAR 788
SAR 1,047 total
includes taxes & fees
25 Oct - 26 Oct
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

14. 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, (4,977 reviews)
"It was in a great area near lots of restaurants, stores and park."
United States
Robin
The price is SAR 884
SAR 1,052 total
includes taxes & fees
1 Oct - 2 Oct
Hilton Chicago/Magnificent Mile Suites

15. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,270 reviews)
"Room were clean and comfortable and staff was helpful."
United States
Guadalupe
The price is SAR 552
SAR 656 total
includes taxes & fees
25 Oct - 26 Oct
Congress Plaza Hotel

16. The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2,113 reviews)
"Great stay"
United States
Fernanda
The price is SAR 559
SAR 665 total
includes taxes & fees
25 Oct - 26 Oct
The Wade

17. 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, (2,683 reviews)
"Great stay, close to great food and ambiance in West Loop."
United States
Victoria
The price is SAR 772
SAR 918 total
includes taxes & fees
29 Oct - 30 Oct
Crowne Plaza Chicago West Loop by IHG

18. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
12.4 km from Woodlawn
9.4 out of 10, Exceptional, (1,006 reviews)
"Nice location, good breakfast Comfortable beds"
United States
Terri
The price is SAR 856
SAR 1,018 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Chicago West Loop Fulton Market Area

19. 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, (2,413 reviews)
"We enjoyed our stay; everything was nearby to walk. Staff was great super nice and we felt so welcomed."
United States
Carmen
The price is SAR 744
SAR 999 total
includes taxes & fees
25 Oct - 26 Oct
Silversmith Hotel Chicago Downtown

20. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 11.7 km from Woodlawn
9.2 out of 10, Wonderful, (1,003 reviews)
"I loved the location, the breakfast, the comfortable bed and the proximity of public transportation."
United States
Jacqueline
The price is SAR 807
SAR 959 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Majestic Chicago Theatre District
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.

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 49 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. Obama Presidential Center and 63rd Street Beach are also a couple of places to visit in the neighborhood. Oak Woods Cemetery, Lorado Taft's Midway Studios, and Stony Island Arts Bank 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 Rockefeller Memorial Chapel or Oriental Institute Museum.
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.