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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, (64 reviews)
"Parking was easy. Just a sign in"
United States
David
The price is NT$1,939
NT$2,414 total
includes taxes & fees
Jun 3 - Jun 4
Best Motel By OYO Chicago I-90

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very Good, (2,944 reviews)
"Great stay"
United States
Agnes Nmabila
The price is NT$3,036
NT$4,175 total
includes taxes & fees
May 25 - May 26
Freehand Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very Good, (10,145 reviews)
"Great stay"
United States
Matthew
The price is NT$3,967
NT$4,716 total
includes taxes & fees
May 8 - May 9
Congress Plaza Hotel

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.4 out of 10, Good, (2,575 reviews)
"Perfect location for a good price that aside, mid hotel "
United States
Nicolas Esteban
The price is NT$3,334
NT$3,964 total
includes taxes & fees
May 27 - May 28
Travelodge by Wyndham Downtown Chicago

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, (2,486 reviews)
"Great place to stay "
United States
Mark
The price is NT$5,813
NT$8,004 total
includes taxes & fees
May 26 - May 27
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, (4,042 reviews)
"It was great property, amazing location and the breakfast was fantastic. "
United States
Nichole
The price is NT$4,260
NT$5,957 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza 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, (583 reviews)
"Great location great staff great hotel!"
United States
Refak
The price is NT$2,964
NT$3,479 total
includes taxes & fees
May 25 - May 26
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, (2,245 reviews)
"This was a great hotel. The staff and accommodations were terrific. I really enjoyed my stay "
United States
Alex
The price is NT$3,776
NT$5,456 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1,003 reviews)
"Everyone was so friendly and the breakfast was nice!"
United States
Angela
The price is NT$3,676
NT$4,371 total
includes taxes & fees
May 10 - May 11
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,220 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is NT$4,718
NT$5,609 total
includes taxes & fees
May 10 - May 11
Aloft Chicago Mag Mile

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.2 km from Woodlawn
8.6 out of 10, Excellent, (3,046 reviews)
"A beautiful historic hotel...we very much enjoyed our stay there."
United States
Michelle
The price is NT$4,037
NT$5,729 total
includes taxes & fees
May 10 - May 11
Warwick Allerton - Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.8 out of 10, Excellent, (3,482 reviews)
"Always a great stay!"
United States
Samantha
The price is NT$3,472
NT$4,128 total
includes taxes & fees
May 25 - May 26
Club Quarters Hotel, Central Loop, Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,773 reviews)
"Clean room and great location "
United States
Diana
The price is NT$5,034
NT$6,916 total
includes taxes & fees
May 25 - May 26
Hilton 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, (1,980 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is NT$4,145
NT$4,928 total
includes taxes & fees
May 26 - May 27
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, (3,297 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is NT$6,516
NT$8,862 total
includes taxes & fees
May 8 - May 9
Swissotel - Chicago

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, (2,689 reviews)
"Great location, right across the street from the park."
United States
Jamison
The price is NT$4,085
NT$4,856 total
includes taxes & fees
May 25 - May 26
Best Western Grant Park Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,159 reviews)
"Excellent location, very clean room and friendly staff"
United States
Alejandra
The price is NT$4,279
NT$5,088 total
includes taxes & fees
May 26 - May 27
River Hotel

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 11.9 km from Woodlawn
8.6 out of 10, Excellent, (2,780 reviews)
"The hotel is good"
United States
Agnes
The price is NT$3,961
NT$5,268 total
includes taxes & fees
May 25 - May 26
La Quinta Inn & Suites by Wyndham Chicago Downtown

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 NT$4,211
NT$5,934 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 13.6 km from Woodlawn
8.6 out of 10, Excellent, (1,977 reviews)
"Very comfortable room, in a convenient location. Good value for money "
United States
Hamit
The price is NT$3,676
NT$5,124 total
includes taxes & fees
May 10 - May 11
Millennium Hotel Knickerbocker 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.

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 Exploration: Woodlawn offers a rich cultural experience with historic houses and local art venues, perfect for those interested in learning about the community.
  • Outdoor Activities: Enjoy outdoor adventures at Woodlawn Park and the Woodlawn Sports Complex, great for families and nature lovers.
  • Charming Neighborhoods: Explore cozy spots and vibrant neighborhoods that provide a friendly atmosphere and recreational opportunities.
  • Shopping and Dining: Discover unique shopping options and delightful cafes, enhancing your urban experience.
  • Diverse Accommodations: Choose from a variety of accommodations, including pet-friendly options and welcoming atmospheres for all travelers.

Find great hotels near Woodlawn

Woodlawn offers a diverse selection of accommodations, perfect for every traveler. From cozy bed & breakfasts to luxurious hotels, you'll find options that cater to both business and leisure needs. Many establishments are pet-friendly and embrace an LGBTQIA-welcoming atmosphere, ensuring a comfortable stay for everyone. Whether you're searching for the best hotels or the well-known Hyatt, Woodlawn has something to suit your vacation desires.

  • Congress Plaza Hotel: Nestled in the vibrant shopping district, Congress Plaza Hotel is a 3.5-star gem that caters to both business travelers and shopping enthusiasts. Located 11.3km away from Woodlawn, this historic hotel offers a blend of classic elegance and modern amenities. Guests can enjoy spacious rooms, a well-equipped business center, and convenient access to nearby shopping venues. The hotel's rich history and stunning architecture create an inviting atmosphere, making it an ideal choice for those seeking a unique urban experience.
  • Hyatt Regency Chicago: As a premier 4-star hotel located 12.9km from Woodlawn, Hyatt Regency Chicago stands out with its eco-certified status and commitment to sustainability. Perfect for business travelers and eco-conscious guests, the hotel features modern accommodations, a state-of-the-art fitness center, and extensive meeting facilities. Situated in the bustling shopping district, guests can easily explore local attractions and retail offerings. With its combination of luxury and environmental responsibility, this hotel is a top choice for those looking to balance work and leisure.
  • Best Western Grant Park Hotel: Located 9.7km from Woodlawn, Best Western Grant Park Hotel is an excellent option for families seeking a comfortable stay. With amenities tailored for children, including free cribs and safety features such as window guards, this hotel ensures a family-friendly environment. Situated in a lively shopping district, it provides easy access to various attractions and dining options. Guests appreciate the warm service and convenient amenities, making it an ideal base for family vacations in Chicago.

Where to stay near Woodlawn

Woodlawn offers a unique blend of culture and tranquility, making it an ideal destination for family-friendly and outdoor vacations. Explore cozy spots and vibrant neighborhoods nearby, where you can enjoy recreational opportunities and friendly atmospheres. Discover local parks, art venues, and charming cafes, all while taking in the scenic beauty of the area. Woodlawn is your gateway to experiencing the warmth of community and the richness of urban life.

  • Chicago: As a vibrant metropolis, Chicago is a must-visit destination that offers a rich blend of cultural experiences and urban attractions. Woodlawn is nestled within this iconic city, making it a convenient base for exploration. Throughout the year, travelers flock to Chicago for its family-friendly activities, outdoor adventures, and city-themed experiences. From world-class shopping districts to renowned theaters and sports facilities, there's something for everyone. Don’t miss iconic landmarks like Millennium Park and the Magnificent Mile, where urban parks and lively tourist precincts create a dynamic atmosphere for visitors.
  • Hyde Park: just 1.6km from Woodlawn, Hyde Park is a charming neighborhood that boasts a strong cultural and educational focus. Known for its historic university, this area is perfect for travelers seeking enriching experiences. With a peak in visitors during the summer months, Hyde Park offers a variety of family-friendly activities and cultural attractions. You can explore the beautiful parks, visit museums, and enjoy shopping at local boutiques. The neighborhood is also home to several events and conferences, catering to both leisure and education-oriented visitors.
  • Washington Park: Located a mile from Woodlawn, Washington Park is an inviting neighborhood steeped in cultural significance and family-oriented activities. Popular for its educational venues and vibrant community, this area attracts visitors year-round. Enjoy access to urban parks and historic colleges, as well as sports facilities that add to the local charm. The summer months see a surge in travelers eager to experience the neighborhood's events and outdoor activities, making it an excellent spot for both relaxation and exploration.

Things to do near Woodlawn

Woodlawn, Chicago, is an ideal destination for culture-themed, family, and outdoor vacations. Visitors can explore the vibrant community through educational activities, enjoy the Woodlawn Sports Complex, and experience outdoor adventures. The area also features shopping options and venues perfect for dream weddings. Whether you're discovering local gems or engaging in arena entertainment, Woodlawn offers a variety of exciting experiences for all ages.

Shopping

For shopping in Woodlawn, visit Chicago Place Mall, 12.9km away, offering a vibrant mix of city and family vibes. Also, check out Shops at North Bridge, 12.9km away, known for entertainment and business. Don't miss Maxwell Street Market, just 9.7km away, for a lively public market experience.

Recreation

At Soldier Field, immerse yourself in the excitement of live sports events and enjoy the vibrant atmosphere. Experience tranquility at Northerly Island Natural Area, where you can connect with nature and unwind. For lively entertainment, visit the House of Blues Chicago, featuring fantastic live music performances.

Adventure

Explore the Salt Creek Trail for a scenic hiking experience, surrounded by nature, located 19.3km from Woodlawn. For thrilling water fun, visit Rainbow Falls Waterpark and Deep River Water Park, both offering exciting rides and family-friendly entertainment, located 25 and 46.7km away, respectively.

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 creating unforgettable memories with loved ones.

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

Booking tips and Expedia advantages for Woodlawn

To save money on your trip to Woodlawn, visit during the off-peak months of December to February when hotel prices are lower. Aim to book your stay on a Monday for the best rates, as Saturdays tend to be the most expensive. Utilize Expedia to find deals by sorting hotel options from lowest to highest price and consider combining hotel, flight, and activity bookings for additional savings. Explore free activities in the area and use public transport, which is budget-friendly, to navigate the city efficiently.

  • 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 refine your preferences, such as your budget, desired location, and the type of hotel you’re looking for. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Woodlawn hotel reservations with your flights and activities through an Expedia package deal.

Find the best attractions near Woodlawn

Woodlawn, Chicago, is a vibrant area perfect for culture-themed, family, and outdoor vacations. Visitors can enjoy attractions like Woodlawn Park and historic houses, alongside relaxing at the nearby beach. The community offers a rich city experience and is ideal for those seeking cultural exploration and family-friendly activities. Don’t miss the chance to visit Woodlawn Hospital, adding a touch of local history to your trip.

  • McCormick Place: As the largest convention center in North America, McCormick Place is a hub for major events and conferences. Its impressive architecture and state-of-the-art facilities create a vibrant business atmosphere, making it an exciting place to explore and network.
  • University of Chicago: This historic university is renowned for its Gothic architecture and stunning campus. With a rich academic heritage, the University of Chicago offers a unique cultural experience, from its libraries to art exhibits that reflect its commitment to scholarship.
  • Chicago Museum of Science and Industry: One of the largest science museums in the world, this interactive museum is perfect for families and culture enthusiasts alike. It features engaging exhibits that explore science, technology, and innovation, making learning fun and accessible.

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 SunnySlightly HighSlightly 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 SunnyAverageSlightly 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 three major airports. Chicago O'Hare International Airport (ORD) is situated 32.2km away, with nearby hotel options like the 4.5-star Loews Chicago O'Hare Hotel and the Hyatt Regency O'Hare, both 3.2km from the airport. Midway International Airport (MDW) is only 11.3km away, featuring luxurious hotels such as The Langham and Nobu Hotel, both 12.9km from the airport. For those flying into Chicago Executive Airport (PWK), located 212.9km away, the 4.5-star Deer Path Inn and Hilton Chicago/Northbrook, just 1.6km away, offer comfortable stays. Each airport provides accessible transportation to these hotels for a seamless travel experience.

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.

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