A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

Chicago Hotel Guide. Hotels in Woodlawn, Chicago, United States of America

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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
3.4 out of 10, (154 reviews)
"A/c working, friendly staff, free parking but messy sheets and a baby mouse in the room"
United States
Saul
The price is €86
includes taxes & fees
25 Oct - 26 Oct
Best Motel By OYO Chicago I-90

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (3,406 reviews)
"Friendly staff, great location"
Canada
Anna
The price is €202
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago

3. 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, (2,744 reviews)
"Excellent stay at a reasonably priced hotel. Will stay again!"
United States
Shelby Ryann
The price is €133
includes taxes & fees
9 Nov - 10 Nov
Best Western Grant Park Hotel

4. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,164 reviews)
"It was a wonderful stay!"
United States
Ashya
The price is €123
includes taxes & fees
10 Nov - 11 Nov
Congress Plaza Hotel

5. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 10.6 km from Woodlawn
9.0 out of 10, Wonderful, (1,002 reviews)
"Amazing location, super helpful staff, and clean/comfortable rooms. I stay here every time I am in town."
United States
Kayla Rene
The price is €142
includes taxes & fees
11 Nov - 12 Nov
Le Méridien Essex Chicago

6. 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, (2,190 reviews)
"Great place to stay at"
United States
Aran
The price is €134
includes taxes & fees
10 Nov - 11 Nov
Hilton Garden Inn Chicago Downtown South Loop

7. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.8 out of 10, Good, (2,901 reviews)
"Great stay"
United States
Sandra
The price is €122
includes taxes & fees
12 Nov - 13 Nov
Travelodge by Wyndham Downtown Chicago

8. 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, (1,227 reviews)
"Great location. We walked to museum campus and millennial park."
United States
Kelsey
The price is €182
includes taxes & fees
4 Nov - 5 Nov
Hilton Vacation Club Hotel Blake Chicago

9. 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, (2,515 reviews)
"Kids loved the pool, location was great for access to museums, and the breakfast was better than I expected!"
United States
Corinn
The price is €152
includes taxes & fees
10 Nov - 11 Nov
Homewood Suites by Hilton Chicago Downtown South Loop

10. 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, (2,724 reviews)
"Very Nice place to stay"
United States
Anand
The price is €122
includes taxes & fees
2 Nov - 3 Nov
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

11. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
14.4 km from Woodlawn
9.0 out of 10, Wonderful, (1,450 reviews)
"Convenient location near good restaurants."
United States
Scott
The price is €161
includes taxes & fees
1 Nov - 2 Nov
Claridge House Chicago, Tapestry Collection by Hilton

12. 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, (2,712 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is €229
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel

13. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.6 km from Woodlawn
8.4 out of 10, Very good, (3,974 reviews)
"Great stay"
United States
KURT
The price is €126
includes taxes & fees
9 Nov - 10 Nov
The Whitehall Hotel, BW Premier Collection

14. 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 €244
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton

15. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,565 reviews)
"Great stay"
United States
Hilary
The price is €256
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago

16. 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, (2,589 reviews)
"Nice stay for the weekend."
United States
Poua
The price is €142
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Chicago - Magnificent Mile

17. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (1,717 reviews)
"Amazing location everything is close by"
United States
Vansh
The price is €152
includes taxes & fees
1 Nov - 2 Nov
Cambria Hotel Chicago Loop - Theatre District

18. 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, (1,663 reviews)
"Great location, friendly staff, tasty breakfast."
United States
William
The price is €116
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Chicago Downtown/Magnificent Mile

19. The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2,143 reviews)
"Had a wonderful stay here"
United States
Erin
The price is €135
includes taxes & fees
12 Nov - 13 Nov
The Wade

20. The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
4.0 star property
River North, 13 km from Woodlawn
8.8 out of 10, Excellent, (1,555 reviews)
"Great hotel and wonderful location"
United States
stephanie
The price is €184
includes taxes & fees
12 Nov - 13 Nov
The RIVVY, Chicago Downtown, a Tribute Portfolio 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 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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Woodlawn Hotel Reviews

Find out more about Woodlawn

Top reasons to visit Woodlawn

  • Cultural Experiences: Woodlawn offers a rich tapestry of American history and vibrant local culture, perfect for immersing oneself in the neighbourhood's heritage.
  • Family-Friendly Activities: The area boasts a variety of family-oriented attractions, ensuring enjoyable outings for visitors of all ages.
  • Outdoor Adventures: With urban parks and nearby beaches, Woodlawn provides a delightful escape for nature enthusiasts and outdoor lovers.
  • Scenic Walks: Easy walking routes allow visitors to explore the neighbourhood's charm and scenic beauty at a leisurely pace.
  • Diverse Accommodation: Woodlawn offers a range of lodging options, from cosy bed and breakfasts to family-friendly hotels, catering to all traveller needs.

Find great hotels near Woodlawn

Discover a variety of accommodation options in Woodlawn, Chicago, designed to cater to all types of travellers. Whether you're seeking a comfortable hotel, a charming bed and breakfast, or pet-friendly facilities for a family getaway, you'll find the perfect stay. With a focus on business amenities and family-friendly experiences, Woodlawn offers an inviting atmosphere for your holiday, ensuring a memorable visit to this vibrant neighbourhood.

  • Congress Plaza Hotel: This 3.5-star hotel embodies a business-friendly atmosphere, making it a perfect choice for corporate travellers seeking a productive stay. Located 11.3km from Woodlawn, the Congress Plaza Hotel offers a range of amenities tailored to business needs, including multiple meeting rooms, a well-equipped business centre, and accessible conference spaces. Nestled in the shopping district, guests can easily indulge in retail therapy after a day of meetings. Its historical charm and professional environment create a unique blend of comfort and functionality for the discerning business traveller.
  • Best Western Grant Park Hotel: Situated just 9.7km from Woodlawn, Best Western Grant Park Hotel is ideal for families and shoppers alike. This welcoming property offers a host of child-friendly amenities, such as free cribs, first aid kits, and window guards, ensuring a safe and enjoyable environment for younger guests. Its prime location in the shopping district allows families to easily explore local attractions and indulge in delightful shopping experiences. The hotel’s accommodating atmosphere and thoughtful facilities make it a commendable choice for those travelling with children.
  • Hyatt Regency Chicago: A 4-star hotel located 12.9km from Woodlawn, Hyatt Regency Chicago stands out with its commitment to inclusivity and eco-friendliness. This property is not only LGBTQIA welcoming but also eco-certified, catering to environmentally conscious travellers. With ample business amenities, including accessible business centres and multiple meeting rooms, it serves as an excellent hub for both work and leisure. The hotel’s modern design combined with its sustainable practices provides a luxurious yet responsible travel experience, making it a top choice for conscious explorers.

Where to stay near Woodlawn

Woodlawn, Chicago, offers a delightful blend of family-friendly charm and vibrant urban life. Visitors can explore the rich tapestry of American history, enjoy the bustling city atmosphere, and revel in the scenic beauty of nearby areas. From cultural experiences to outdoor adventures, Woodlawn is perfect for those seeking a unique travel experience. Embrace the friendly spirit of the neighbourhood while discovering its attractions and the allure of city living.

  • Chicago: As a vibrant city, Chicago offers an exhilarating blend of urban attractions and cultural experiences. Situated in the heart of the Midwest, it boasts a rich history and is renowned for its stunning architecture and diverse neighbourhoods. Visitors can indulge in a variety of activities, from shopping along the Magnificent Mile to enjoying world-class theatre and arena entertainment. Iconic landmarks such as the Willis Tower and Millennium Park are must-visit spots, ensuring an unforgettable travel experience.
  • Hyde Park: Just 1.6km away from Woodlawn, Hyde Park is a culturally rich neighbourhood that is home to the prestigious University of Chicago. This area invites travellers with its beautiful parks and historic sites, offering a perfect family-friendly atmosphere. Visitors can explore the renowned Museum of Science and Industry, enjoy outdoor activities, or partake in local shopping. Its charming streets and vibrant community make Hyde Park a delightful place to experience the essence of Chicago’s intellectual and cultural life.
  • Washington Park: Also located a mile from Woodlawn, Washington Park is known for its lush greenery and historical significance. This neighbourhood features an urban park that provides plenty of outdoor activities, making it ideal for families and culture enthusiasts alike. Visitors can enjoy educational experiences and explore local attractions such as the historic college university and the nearby stadium. With its inviting atmosphere and recreational spaces, Washington Park is a lovely spot to unwind and connect with nature in the bustling city.

Things to do near Woodlawn

Woodlawn offers a delightful blend of family-friendly activities and cultural experiences. Visitors can explore educational attractions, enjoy arena entertainment, and relax in recreational areas. Ideal for sightseeing, Woodlawn also features easy walks and culinary tours, allowing tourists to savour local flavours. This vibrant neighbourhood is perfect for those seeking a mix of outdoor adventures and cultural immersion during their stay.

Shopping

In Woodlawn, you can visit Third World Press, a charming store just 3.2km away, perfect for unique gifts. For a larger shopping experience, head to Chicago Place Mall or 900 North Michigan Shops, both located 12.9km away, offering a variety of shops and entertainment options.

Recreation

Experience the electric atmosphere at Soldier Field, where you can catch a game or enjoy the vibrant sports culture. For a serene escape, head to Northerly Island Natural Area, perfect for relaxation and connecting with nature. Unwind with live music at the House of Blues Chicago, where entertainment meets soul.

Adventure

Embark on an adventurous hike along the Salt Creek Trail, located 19.3km from Woodlawn, where scenic views and nature's beauty await. For family fun, visit the Deep River Water Park, 46.7km away, or Rainbow Falls Waterpark, 40.2km away, both offering thrilling rides and entertainment.

Nightlife

Experience the vibrant nightlife in Woodlawn with a visit to the Chicago Theatre, offering a cultural and romantic atmosphere just 11.3km away. For film lovers, Film Row Cinema is 9.7km away, providing a charming cinematic experience. Don’t miss the adventure at Amazing Chicago's Funhouse Maze, located 12.9km away.

*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 visit to Woodlawn, consider travelling between December and February when prices are lower. Booking your stay for a Monday will also help reduce costs, as Saturday is the priciest day. Utilise Expedia’s search tool to find affordable hotels and arrange package deals that combine flights and activities for additional savings. Don’t forget to explore free activities in the area and make the most of public transport to keep travel expenses down.

  • 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, preferred location, and the type of hotel you desire. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: By booking an Expedia package, you can save money by combining your Woodlawn hotel stay with your flights and activities.

Find the best attractions near Woodlawn

Woodlawn offers a delightful blend of family-friendly activities, cultural experiences, and outdoor adventures. Visitors can explore urban parks, historic houses, and nearby beaches, making it an ideal destination for those seeking both city life and a touch of nature. With a variety of attractions catering to culture enthusiasts and families alike, Woodlawn promises an enriching and enjoyable holiday experience.

  • McCormick Place: As the largest convention centre in North America, McCormick Place offers a dynamic atmosphere for various events. Its impressive size and modern facilities create a vibrant business environment, making it an ideal spot for conferences and exhibitions.
  • University of Chicago: Renowned for its stunning Gothic architecture and rich academic tradition, the University of Chicago is a cultural gem. Stroll through its historic campus, visit the esteemed libraries, and enjoy the serene gardens, all while soaking in the scholarly vibes.
  • Chicago Museum of Science and Industry: This engaging museum is perfect for families, featuring interactive exhibits that celebrate innovation and discovery. Explore fascinating displays on science, technology, and industry, making it a memorable experience for visitors of all ages.

Best time to go to Woodlawn

The best time to visit Woodlawn can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Woodlawn falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Woodlawn falls in January, 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

Accessing Woodlawn, Chicago, is convenient via its major airports. Chicago O'Hare International Airport (ORD) is approximately 32.2km away, with nearby hotels like the 4.5-star Loews Chicago O'Hare Hotel and the 4-star Hyatt Regency O'Hare, both just 3.2km from the airport. Midway International Airport (MDW) is closer at about 11.3km, offering luxurious options such as the 5-star Trump International Hotel & Tower and Nobu Hotel, both within 14.5km. For those considering Chicago Executive Airport (PWK), located 45.1km away, the 4.5-star Deer Path Inn and 4-star Hilton Chicago/Northbrook provide comfortable accommodations, with easy access to the airport.

Frequently asked questions

What's it like in Woodlawn?
Woodlawn is a neighbourhood that travellers 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 neighbourhood.
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 are there 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 accommodation options to choose from.
If I need to cancel my hotel reservation in Woodlawn, will I receive a refund?
Yes, the majority of hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Enter dates in and click on "Search", then filter by "fully refundable" to view the best deals available in Woodlawn.
What can I see and do in this Chicago neighbourhood?
Spend some time exploring the great outdoors at Lake Michigan, Jackson Park and Bob-O-Link Meadow. Obama Presidential Center and Lorado Taft's Midway Studios are also a couple of places to visit in the neighbourhood. 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, make sure that you visit other sights such as 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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