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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
2.0 star property
Woodlawn
3.6 out of 10, (83 reviews)
"This is not a good place."
United States
Dinesh Kumar
The price is €68
includes taxes & fees
12 Jul - 13 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, (2,538 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is €261
includes taxes & fees
7 Jul - 8 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.1 km from Woodlawn
9.2 out of 10, Wonderful, (1,802 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is €164
includes taxes & fees
30 Jun - 1 Jul
Omni Chicago Hotel

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, (2,493 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is €220
includes taxes & fees
1 Jul - 2 Jul
Palmer House a Hilton Hotel

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very good, (1,853 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is €201
includes taxes & fees
2 Jul - 3 Jul
The Wade

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,380 reviews)
"The property was clean and the location was perfect!"
United States
Martha
The price is €208
includes taxes & fees
1 Jul - 2 Jul
Swissotel - 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, (2,243 reviews)
"Great location"
United States
Gabino
The price is €160
includes taxes & fees
5 Jul - 6 Jul
Silversmith Hotel Chicago Downtown

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,637 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is €165
includes taxes & fees
1 Jul - 2 Jul
Eurostars 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, (4,412 reviews)
"The breakfast, location, and staff were amazing."
United States
Corey
The price is €190
includes taxes & fees
30 Jun - 1 Jul
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, (10,248 reviews)
"Great stay thanks"
United States
Felipa
The price is €140
includes taxes & fees
29 Jun - 30 Jun
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, (2,627 reviews)
"Great location and helpful staff."
United States
Ming
The price is €139
includes taxes & fees
1 Jul - 2 Jul
Travelodge by Wyndham Downtown Chicago

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, (3,732 reviews)
"Great location, excellent room and amenities proactively attentive staff."
United States
Robert
The price is €251
includes taxes & fees
1 Jul - 2 Jul
LondonHouse Chicago, Curio Collection by Hilton

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, (1,089 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is €169
includes taxes & fees
6 Jul - 7 Jul
Staypineapple, An Iconic Hotel, The Loop

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,851 reviews)
"Great stay"
United States
Jose saul
The price is €227
includes taxes & fees
2 Jul - 3 Jul
Hilton Chicago

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (2,187 reviews)
"Easy check in , helpful staff , convenient location ."
United States
MIRCEA
The price is €231
includes taxes & fees
7 Jul - 8 Jul
Fairmont Chicago at Millennium Park

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,658 reviews)
"Excellent location."
United States
Mirna
The price is €236
includes taxes & fees
5 Jul - 6 Jul
Sheraton Grand Chicago Riverwalk

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
The Loop, 10.8 km from Woodlawn
9.0 out of 10, Wonderful, (1,009 reviews)
"Great location, clean hotel, and very accommodating staff."
United States
Neydee
The price is €186
includes taxes & fees
5 Jul - 6 Jul
The Blackstone, Autograph Collection

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,508 reviews)
"Staff was great."
United States
Marianne
The price is €232
includes taxes & fees
1 Jul - 2 Jul
Hyatt Regency Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 11.7 km from Woodlawn
8.4 out of 10, Very good, (1,011 reviews)
"Great stay!"
United States
Alondra
The price is €174
includes taxes & fees
2 Jul - 3 Jul
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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, (3,937 reviews)
"Nice location and friendly staff"
United States
James
The price is €144
includes taxes & fees
30 Jun - 1 Jul
The Whitehall Hotel, BW Premier Collection
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 47 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. 63rd Street Beach 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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