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Find hotels in Woodlawn, Chicago from AED 267

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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
3.4 out of 10, (48)
"Clean room "
United States
Pierre
The price is AED 206
AED 267 total
includes taxes & fees
13 Jan - 14 January 2026
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, (2266)
"Great staff and restaurants!!"
United States
Abigale
The price is AED 340
AED 525 total
includes taxes & fees
6 Jan - 7 January 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very Good, (1522)
"Great staff and great location. "
United States
Joe
The price is AED 371
AED 435 total
includes taxes & fees
21 Dec - 22 Dec
The Wade

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3020)
"Very beautiful place to stay"
United States
FaithBrenda
The price is AED 419
AED 599 total
includes taxes & fees
1 Jan - 2 January 2026
Swissotel - Chicago

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, (2748)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is AED 285
AED 442 total
includes taxes & fees
11 Jan - 12 January 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2197)
"Yes, very clean room and great hospitality "
United States
leticia i Vasquez
The price is AED 328
AED 385 total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Chicago - Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.2 km from Woodlawn
8.6 out of 10, Excellent, (1787)
"Hotel was amazing all around! Friendly and very helpful staff. Clean rooms and a Starbucks! "
United States
Alicia
The price is AED 514
AED 699 total
includes taxes & fees
28 Dec - 29 Dec
Radisson Blu Aqua Hotel Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2967)
"Great location and great staff!!"
United States
lynne
The price is AED 290
AED 341 total
includes taxes & fees
14 Jan - 15 January 2026
Aloft Chicago Mag Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.8 out of 10, Excellent, (1041)
"Staff was amazing! "
United States
Ahren
Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 13.7 km from Woodlawn
8.6 out of 10, Excellent, (2294)
"Excellent hotel. Loved staying there"
United States
cristina
The price is AED 364
AED 427 total
includes taxes & fees
4 Jan - 5 January 2026
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Streeterville, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1004)
"Great ubicación and great breakfast "
United States
Andrea
The price is AED 279
AED 328 total
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3402)
"I always love staying at this place when I visit"
Canada
William
The price is AED 499
AED 694 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency 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, (3495)
"Great place to stay "
United States
RaShawna
The price is AED 298
AED 350 total
includes taxes & fees
5 Jan - 6 January 2026
Hilton Chicago/Magnificent Mile Suites

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Streeterville, 13.6 km from Woodlawn
8.6 out of 10, Excellent, (2006)
"Great location, clean hotel"
United States
Andre
The price is AED 327
AED 470 total
includes taxes & fees
17 Dec - 18 Dec
Millennium Knickerbocker Chicago

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 13 km from Woodlawn
9.0 out of 10, Wonderful, (1053)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is AED 360
AED 530 total
includes taxes & fees
1 Jan - 2 January 2026
Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1600)
"Great stay!!"
United States
Adrian
The price is AED 359
AED 421 total
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Chicago Magnificent Mile

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, (1171)
"The room was spacious and clean and it was a good value."
United States
Dj
The Chicago Hotel Collection - Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 13.1 km from Woodlawn
8.0 out of 10, Very Good, (1345)
"Very happy with my two stays here. "
United States
Courteney
The price is AED 320
AED 376 total
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn Chicago Downtown/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, (2980)
"Excellent stay great location and great rooms"
United States
Joseph
The price is AED 366
AED 533 total
includes taxes & fees
21 Dec - 22 Dec
Hotel Riu Plaza Chicago

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 10.4 km from Woodlawn
8.2 out of 10, Very Good, (2649)
"Great staff & Great location. "
United States
Gabrielle
The price is AED 264
AED 310 total
includes taxes & fees
5 Jan - 6 January 2026
Best Western Grant Park Hotel
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 Michigan Avenue and Navy Pier 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.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Top Woodlawn Hotel Reviews

Find out more about Woodlawn

Top reasons to visit Woodlawn

  • Vibrant Cultural Experience: Woodlawn offers a unique blend of urban energy and family-friendly charm, perfect for exploring local history.
  • Recreational Opportunities: Enjoy scenic parks, outdoor adventures, and relaxing spots like Woodlawn Park.
  • Educational Attractions: Discover historic houses and engaging activities that cater to all ages.
  • Diverse Accommodation: A range of hotels and charming bed and breakfasts meet various traveler needs and preferences.
  • Local Shopping and Dining: Experience friendly local shops and eateries that highlight the neighborhood's warmth and vibrancy.

Find great hotels near Woodlawn

Explore a variety of hotel accommodations in Woodlawn, Chicago, catering to every traveler's needs. Whether you're seeking luxurious stays, pet-friendly options, or a welcoming environment for LGBTQIA travelers, Woodlawn has it all. From reliable business facilities to charming bed and breakfasts, you'll find the perfect hotel for your visit, including well-known brands like Hyatt. Discover the best hotels that promise a memorable experience in this vibrant neighborhood.

  • Congress Plaza Hotel: This 3.5-star hotel offers a blend of historic charm and modern convenience, making it an ideal choice for travelers seeking a vibrant shopping and business experience. Located 11.3km from Woodlawn, the Congress Plaza Hotel features spacious rooms with elegant decor and essential amenities. Guests can enjoy on-site dining options, a fitness center, and easy access to Chicago’s renowned shopping district. Its proximity to iconic attractions and a welcoming atmosphere ensure a delightful stay for both leisure and business visitors.
  • Hyatt Regency Chicago: A 4-star eco-certified hotel located 12.9km from Woodlawn, the Hyatt Regency Chicago stands out for its commitment to sustainability and inclusivity. This modern hotel is perfect for travelers who prioritize eco-friendly practices and LGBTQIA-friendly environments. Guests can indulge in stylish accommodations, an array of dining options, and exceptional amenities, including a fitness center and event spaces. Nestled in the bustling shopping district, it’s a great base for exploring the vibrant city while enjoying a comfortable and welcoming atmosphere.
  • Best Western Grant Park Hotel: Situated 9.7km from Woodlawn, the Best Western Grant Park Hotel is a family-friendly lodging option that caters especially to those traveling with children. This hotel provides a range of amenities tailored for families, such as free cribs, a first aid kit, and window guards to ensure safety for younger guests. Located in the shopping district, it offers easy access to local attractions and dining options, making it a convenient choice for family vacations while maintaining a relaxed and inviting ambiance.

Where to stay near Woodlawn

Woodlawn, a vibrant neighborhood in Chicago, offers a rich cultural experience perfect for families and outdoor enthusiasts. Explore cozy spots and recreational opportunities nearby, including scenic parks and friendly local shops. The atmosphere is a delightful mix of urban energy and family-friendly charm, making it an ideal base for your vacation. Don't miss the chance to immerse yourself in the unique vibes of Woodlawn and its welcoming surrounding areas.

  • Chicago: As a vibrant metropolis, Chicago offers an exhilarating mix of culture, entertainment, and outdoor activities. Woodlawn, situated within its borders, makes for an ideal base to explore the city. While visitor numbers peak during the summer months, Chicago's charm is year-round. Travelers flock here for family outings, outdoor adventures, and city-themed experiences. Must-visit attractions include the renowned shopping districts, thrilling arena events, and captivating theaters. Don’t miss local landmarks such as sports stadiums and lush urban parks, perfect for leisurely strolls or picnics.
  • Hyde Park: Located just 1.6km away from Woodlawn, Hyde Park is a culturally rich neighborhood that attracts visitors throughout the year. Peak travel times occur in April and during the summer months, making it a lively spot for families and culture enthusiasts alike. The area is home to the historic University of Chicago, offering educational experiences alongside beautiful urban parks. Enjoy shopping, attend events at local venues, or immerse yourself in the vibrant arts scene. Its unique blend of history and modernity creates a captivating experience for all.
  • Washington Park: Also 1.6km away from Woodlawn, Washington Park is an inviting neighborhood known for its cultural vibrancy and family-friendly atmosphere. Visitors typically come during the late summer and early fall months. The area features numerous educational opportunities, shopping, and exciting entertainment options. Key local attractions include historic universities, expansive urban parks, and sports facilities. Whether you’re exploring the rich history or enjoying a day at the park, Washington Park is a delightful destination that complements your Chicago adventure.

Things to do near Woodlawn

Woodlawn offers a vibrant blend of cultural experiences perfect for family outings and outdoor adventures. Visitors can explore the neighborhood’s rich history while enjoying educational attractions, shopping areas, and an arena entertainment facility. Whether you're planning a dream wedding or simply looking to discover the local charm, Woodlawn provides a welcoming atmosphere for all types of vacations.

Shopping

For shopping in Woodlawn, visit Chicago Place Mall, 12.9km away, offering a vibrant city atmosphere. Also, explore Shops at North Bridge, 12.9km away, known for entertainment and family-friendly options. Don’t miss Maxwell Street Market, 9.7km away, featuring unique local goods in a lively setting.

Recreation

At Soldier Field, immerse yourself in the excitement of live sports events and vibrant energy. Northerly Island Natural Area offers a serene escape with nature trails perfect for relaxation and reflection. Enjoy soulful music and a lively atmosphere at the House of Blues Chicago for an unforgettable evening.

Adventure

Embark on an adventure at Salt Creek Trail, a scenic hiking trail located 19.3km from Woodlawn, perfect for nature enthusiasts. For family fun, visit Rainbow Falls Waterpark or Deep River Water Park, both offering thrilling rides and entertainment, located 25 and 46.7km away, respectively.

Nightlife

Experience the vibrant nightlife in Woodlawn. Catch a show at the Chicago Theatre, just 11.3km away, for a cultural night out. Enjoy a film at Film Row Cinema, 9.7km away, perfect for family fun. For adventure, explore Amazing Chicago's Funhouse Maze, located 12.9km from Woodlawn.

*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, consider visiting during the off-peak months of December to February when hotel prices are lower. Mondays are the least expensive days to stay, while Saturdays are the priciest. Utilize Expedia's search tool to find great deals by filtering options from lowest to highest price. Combine your hotel, flights, and activities in an Expedia package for additional savings. For budget-friendly transportation, walking is a great option, as the area is easily navigable on foot, allowing you to explore without the cost of public transport.

  • 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 narrow down your options based on your budget, preferred location, and desired hotel type. To find the best prices and deals, simply 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 offers a vibrant cultural experience perfect for family and outdoor vacations. Visitors can explore urban parks, historic houses, and nearby beaches, catering to those seeking a city adventure. Don’t miss the local highlights like Woodlawn Hospital and Woodlawn Park, which provide additional activities and relaxation spots. This charming neighborhood promises a rich blend of history and recreation for all travelers.

  • McCormick Place: As one of the largest convention centers in North America, McCormick Place offers a bustling atmosphere filled with trade shows and exhibitions. Its state-of-the-art facilities make it a hub for business and innovation, perfect for networking and discovering new industry trends.
  • University of Chicago: Renowned for its Gothic architecture and rich academic history, the University of Chicago exudes a cultural vibe. Explore its beautiful campus, visit the smart bookstores, and immerse yourself in the intellectual atmosphere that has shaped many great thinkers.
  • Chicago Museum of Science and Industry: This family-friendly museum offers interactive exhibits that engage visitors of all ages. From a WWII submarine to a coal mine, the museum combines culture with science, making learning fun and memorable for everyone.

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 32.2km away and offers nearby hotels like Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare Chicago, both just 3.2km from the airport. Chicago Midway International Airport (MDW) is closer at 11.3km, with luxurious options such as The Langham, Chicago and Nobu Hotel Chicago. For those considering Chicago Executive Airport (PWK), located 45.1km away, nearby accommodations include Deer Path Inn and Hilton Chicago/Northbrook, both just 1.6km from the airport. Each hotel provides easy access to their respective airports, ensuring a smooth arrival to Woodlawn.

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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 46 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.