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

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (103 reviews)
"Clean room"
United States
Roger
The price is €103
includes taxes & fees
27 Jul - 28 Jul
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, (2,601 reviews)
"View was beautiful, accommodations were excellent."
United States
Julie
The price is €300
includes taxes & fees
9 Aug - 10 Aug
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (1,923 reviews)
"The staff was always super helpful, our room was clean and very comfortable, the view to the lake was beautiful!"
United States
Raul
The price is €176
includes taxes & fees
19 Jul - 20 Jul
The Wade

FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
3.0 star property
River North, 13.1 km from Woodlawn
7.0 out of 10, Good, (9 reviews)
"Overall was a good stay!! Wish the place next door wasn’t as loud at night."
United States
Lia
The price is €170
includes taxes & fees
26 Jul - 27 Jul
FOUND Hotels, Chicago, Series by Marriott

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.2 km from Woodlawn
8.6 out of 10, Excellent, (3,033 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is €174
includes taxes & fees
11 Aug - 12 Aug
Warwick Allerton - Chicago

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 11.7 km from Woodlawn
9.4 out of 10, Exceptional, (2,296 reviews)
"Wonderful stay"
United States
Taylor
The price is €193
includes taxes & fees
9 Aug - 10 Aug
Silversmith Hotel Chicago Downtown

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, (2,527 reviews)
"Staff was very nice. Hotel is beautiful "
United States
Britney Q
The price is €252
includes taxes & fees
9 Aug - 10 Aug
Palmer House a Hilton Hotel

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.6 out of 10, Good, (2,706 reviews)
"My stay was great! Staff was friendly and helpful."
United States
Danny
The price is €183
includes taxes & fees
12 Aug - 13 Aug
Travelodge by Wyndham Downtown Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,739 reviews)
"Nice place great staff and a great location"
United States
Byron
The price is €208
includes taxes & fees
27 Jul - 28 Jul
Eurostars Magnificent Mile

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,254 reviews)
"We’ve stayed there twice and probably will again."
United States
Ashley
The price is €197
includes taxes & fees
10 Aug - 11 Aug
Congress Plaza Hotel

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, (1,744 reviews)
"Nice place to stay"
Australia
Anna
The price is €171
includes taxes & fees
27 Jul - 28 Jul
The Chicago Hotel Collection Ambassador Gold Coast

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, (3,800 reviews)
"Beautiful hotel and location. Staff were very friendly and kind."
Canada
Sophie
The price is €258
includes taxes & fees
6 Aug - 7 Aug
LondonHouse Chicago, Curio Collection by Hilton

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
7.8 out of 10, Good, (3,192 reviews)
"Great location, affordable, comfortable bed, great air conditioning and plenty of hot water great water pressure in the shower."
United States
Traci
The price is €150
includes taxes & fees
10 Aug - 11 Aug
Freehand Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 13.3 km from Woodlawn
8.8 out of 10, Excellent, (2,332 reviews)
"I liked the ambiance of the hotel, everyone was nice and it was very clean."
United States
Tanil
The price is €201
includes taxes & fees
9 Aug - 10 Aug
The Godfrey Hotel Chicago

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, (1,146 reviews)
"Beautiful historic building; dog friendly!"
United States
Zoe
The price is €243
includes taxes & fees
9 Aug - 10 Aug
Staypineapple, An Iconic Hotel, The Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,484 reviews)
"Great hotel and location."
Canada
Lubisa
The price is €292
includes taxes & fees
6 Aug - 7 Aug
Swissotel - Chicago

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1,041 reviews)
The price is €263
includes taxes & fees
19 Jul - 20 Jul
theWit Chicago, a Hilton Hotel

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, (2,098 reviews)
"Overall it was a nice place to stay"
United States
Nathaniel
The price is €167
includes taxes & fees
9 Aug - 10 Aug
Hilton Garden Inn Chicago Downtown South Loop

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.1 km from Woodlawn
9.6 out of 10, Exceptional, (1,280 reviews)
"Comfortable hotel in a good location. Lots of public transportation close."
United States
Dean
The price is €191
includes taxes & fees
9 Aug - 10 Aug
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
11.7 km from Woodlawn
9.4 out of 10, Exceptional, (166 reviews)
"Clean, new, and cozy stay in a great location."
United States
Pedro
The price is €191
includes taxes & fees
19 Jul - 20 Jul
LIVN - West Loop 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 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 48 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 63rd Street Beach are also a couple of places to visit in the neighbourhood. 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, make sure that you visit other sights such as 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.

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