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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"
United States
Sydney
The price is NT$2,571
NT$3,199 total
includes taxes & fees
May 3 - May 4
Best Motel By OYO Chicago I-90

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, (2,392 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is NT$5,639
NT$7,494 total
includes taxes & fees
May 9 - May 10
Palmer House a Hilton Hotel

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, (2,444 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is NT$7,935
NT$10,391 total
includes taxes & fees
Apr 26 - Apr 27
Sable at Navy Pier Chicago, Curio Collection by Hilton

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 13.1 km from Woodlawn
8.6 out of 10, Excellent, (555 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is NT$2,806
NT$3,294 total
includes taxes & fees
Apr 26 - Apr 27
FOUND Hotel Chicago River North

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very Good, (2,882 reviews)
"Was nice! "
Canada
Emilie
The price is NT$2,600
NT$4,535 total
includes taxes & fees
Apr 21 - Apr 22
Freehand Chicago

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.2 km from Woodlawn
7.6 out of 10, Good, (1,300 reviews)
"Amazing stay "
United States
Napoleon
The price is NT$3,636
NT$4,269 total
includes taxes & fees
Apr 26 - Apr 27
The Chicago Hotel Collection - Magnificent Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,878 reviews)
"Great hotel "
United States
Marina
The price is NT$3,949
NT$5,526 total
includes taxes & fees
Apr 26 - Apr 27
Hotel Riu Plaza Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very Good, (10,135 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is NT$3,636
NT$4,268 total
includes taxes & fees
Apr 26 - Apr 27
Congress Plaza Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,186 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is NT$4,076
NT$4,785 total
includes taxes & fees
Apr 26 - Apr 27
Aloft Chicago Mag Mile

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,090 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is NT$4,076
NT$4,785 total
includes taxes & fees
Apr 19 - Apr 20
River Hotel

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, (3,926 reviews)
"Loved the stay here !"
United States
Alisha
The price is NT$4,562
NT$5,356 total
includes taxes & fees
Apr 26 - Apr 27
L7 Chicago by LOTTE

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,732 reviews)
"We love staying here "
United States
Carrie
The price is NT$6,287
NT$8,403 total
includes taxes & fees
May 8 - May 9
Hilton 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, (2,236 reviews)
"Great stay!"
United States
Jessica
The price is NT$3,768
NT$5,387 total
includes taxes & fees
Apr 26 - Apr 27
Silversmith Hotel Chicago Downtown

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 14.4 km from Woodlawn
8.2 out of 10, Very Good, (1,372 reviews)
"Very beautiful place to stay"
United States
angie
The price is NT$4,228
NT$4,964 total
includes taxes & fees
Apr 21 - Apr 22
The Chicago Hotel Collection Ambassador Gold Coast

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, (1,043 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is NT$4,237
NT$5,963 total
includes taxes & fees
May 10 - May 11
Staypineapple, An Iconic Hotel, The Loop

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 13 km from Woodlawn
8.4 out of 10, Very Good, (1,876 reviews)
"Great location and a very high class hotel."
United States
Cornelius
The price is NT$3,068
NT$3,664 total
includes taxes & fees
Apr 28 - Apr 29
Hotel Saint Clair- Magnificent Mile

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,083 reviews)
"For the price, it was a very nice a room and location. "
United States
Anna
The price is NT$3,464
NT$4,067 total
includes taxes & fees
Apr 27 - Apr 28
Central Loop Hotel

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,085 reviews)
"Great location and very clean hotel with nice staff. "
United States
Carrie
The price is NT$4,231
NT$5,909 total
includes taxes & fees
Apr 26 - Apr 27
Arlo Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,424 reviews)
"Great stay"
United States
Ashley
The price is NT$4,044
NT$4,748 total
includes taxes & fees
Apr 26 - Apr 27
Eurostars Magnificent Mile

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, (2,186 reviews)
"Great stay!"
United States
Hannah
The price is NT$4,076
NT$4,785 total
includes taxes & fees
Apr 19 - Apr 20
Club Quarters Hotel Wacker at Michigan, 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.

O'Hare

Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

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.

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 50 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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