Photo by Tanesha Thompson

Woodlawn Hotels near Chicago

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Woodlawn, Chicago

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 P3,871
P5,016 total
includes taxes & fees
Nov 25 - Nov 26
Best Motel By OYO Chicago I-90

Eurostars Magnificent Mile

4.0 star property
River North, 13.1 km from Woodlawn
8.8 out of 10, Excellent, (3108)
"Location was great "
United States
Hamik
The price is P6,652
P7,809 total
includes taxes & fees
Dec 21 - Dec 22
Eurostars Magnificent Mile

River Hotel

4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (4819)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is P5,402
P6,341 total
includes taxes & fees
Nov 23 - Nov 24
River Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2138)
"Great stay "
United States
Melinda
The price is P5,757
P6,758 total
includes taxes & fees
Nov 26 - Nov 27
DoubleTree by Hilton Chicago - Magnificent Mile

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (4050)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is P6,600
P7,748 total
includes taxes & fees
Dec 16 - Dec 17
citizenM Chicago Downtown

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, (2239)
"Room was spotless…staff was great!"
United States
Tamika
The price is P5,074
P7,963 total
includes taxes & fees
Dec 16 - Dec 17
Sable at Navy Pier Chicago, Curio Collection by Hilton

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2915)
"Great location!!"
United States
sarah e
The price is P5,723
P6,718 total
includes taxes & fees
Nov 24 - Nov 25
Aloft Chicago Mag Mile

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 13.6 km from Woodlawn
9.0 out of 10, Wonderful, (3334)
"Great stay!"
United States
Rose
The price is P4,914
P5,769 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago

4.0 star property
The Loop, 10.7 km from Woodlawn
8.4 out of 10, Very Good, (2305)
"Clean Rooms & very nice staff"
United States
Teresa
The price is P6,234
P9,047 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Chicago

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 12.8 km from Woodlawn
8.4 out of 10, Very Good, (4181)
"Great location. "
United States
Rodger
The price is P4,484
P5,263 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Freehand Chicago

4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very Good, (2584)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is P4,720
P6,579 total
includes taxes & fees
Dec 15 - Dec 16
Freehand Chicago

FOUND Hotel Chicago River North

2.0 star property
River North, 13.1 km from Woodlawn
8.4 out of 10, Very Good, (331)
"very clean and modern, staff was very friendly"
United States
Edrick
The price is P3,985
P4,678 total
includes taxes & fees
Dec 7 - Dec 8
FOUND Hotel Chicago River North

Congress Plaza Hotel

3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very Good, (9607)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is P5,757
P6,758 total
includes taxes & fees
Nov 24 - Nov 25
Congress Plaza Hotel

Crowne Plaza Chicago West Loop by IHG

3.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1687)
"The location was great!!"
United States
Yvette
The price is P5,310
P6,233 total
includes taxes & fees
Dec 14 - Dec 15
Crowne Plaza Chicago West Loop by IHG

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (2819)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is P6,098
P8,819 total
includes taxes & fees
Dec 16 - Dec 17
Hotel Riu Plaza Chicago

Hyatt Centric The Loop Chicago

4.0 star property
Theatre District, 11.7 km from Woodlawn
9.0 out of 10, Wonderful, (2244)
"Clean room, friendly staff, convenient location. "
United States
Arthera
The price is P8,780
P10,308 total
includes taxes & fees
Dec 21 - Dec 22
Hyatt Centric The Loop Chicago

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 11.7 km from Woodlawn
9.2 out of 10, Wonderful, (2074)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown

Best Western Grant Park Hotel

2.5 star property
The Loop, 10.4 km from Woodlawn
8.2 out of 10, Very Good, (2611)
"Loved our stay here! Was easy to check in and staff was super friendly! Loved the area and the walk to millennium park was nice."
United States
Mary
The price is P4,764
P5,592 total
includes taxes & fees
Dec 4 - Dec 5
Best Western Grant Park Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 11.7 km from Woodlawn
8.4 out of 10, Very Good, (2074)
"Great place to stay."
United States
Aaron
The price is P6,047
P8,573 total
includes taxes & fees
Dec 21 - Dec 22
Palmer House a Hilton Hotel

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3396)
"Great stay"
United States
Jenine
The price is P7,925
P9,303 total
includes taxes & fees
Dec 18 - Dec 19
LondonHouse Chicago, Curio Collection by Hilton
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.

Hotels in Woodlawn with free breakfast

Hotels in Woodlawn with a pool

Top guest rated hotels in Woodlawn

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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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 Richness: Woodlawn boasts a vibrant cultural scene with local art galleries and historical sites that reflect the community's heritage.
  • Outdoor Activities: Enjoy numerous urban parks perfect for family outings, leisurely strolls, or even romantic picnics.
  • Local Dining: Experience a variety of cafes and restaurants that offer a taste of the local cuisine and friendly atmosphere.
  • Proximity to Chicago: Easily access the iconic skyline and attractions of downtown Chicago while enjoying the charm of a quieter neighbourhood.
  • Diverse Accommodations: Choose from luxurious hotels to cosy bed and breakfasts, catering to all types of travellers.

Find great hotels near Woodlawn

Discover the charm of Woodlawn, Chicago, where a variety of accommodations await to suit every traveller's needs. From luxurious hotels to cosy bed and breakfasts, you’ll find options that cater to business travellers, pet owners, and those seeking an LGBTQIA-friendly experience. Whether you’re looking for a Hyatt hotel or the best local gems, Woodlawn offers a welcoming retreat for a memorable vacation.

  • Congress Plaza Hotel: A distinguished 3.5-star establishment, Congress Plaza Hotel offers a perfect blend of historical charm and modern convenience, situated 11.3km from Woodlawn. Ideal for business travellers and shopping enthusiasts alike, this hotel is nestled in the heart of the shopping district. Guests will appreciate the spacious rooms, extensive meeting facilities, and on-site dining options. With its central location, visitors can easily explore Chicago's vibrant retail scene and cultural attractions, making it a smart choice for both leisure and work.
  • Hyatt Regency Chicago: This eco-certified 4-star hotel is located 12.9km from Woodlawn, making it an excellent choice for environmentally-conscious travellers seeking a city-themed getaway. The Hyatt Regency Chicago boasts a contemporary design with a commitment to sustainability, featuring energy-efficient amenities and a prime location in the bustling shopping district. Guests can enjoy a range of services including a fitness centre, on-site dining, and spacious rooms with stunning city views, ensuring a comfortable and eco-friendly stay in the heart of the city.
  • Best Western Grant Park Hotel: Located just 9.7km from Woodlawn, Best Western Grant Park Hotel is particularly suited for families seeking both comfort and convenience. The hotel provides an array of family-friendly amenities, including cribs, window guards for children, and a First Aid kit, ensuring peace of mind for parents. Situated in the shopping district, guests can easily access local attractions and enjoy spacious accommodations that cater to families, making it a delightful option for those travelling with children.

Where to stay near Woodlawn

Woodlawn, Chicago, offers a delightful mix of cultural experiences and recreational opportunities for families and outdoor enthusiasts. Explore the nearby parks for a breath of fresh air, visit local art galleries, or enjoy the friendly atmosphere at bustling cafes. Just a short distance away, the vibrant city of Chicago beckons with its iconic skyline, while the serene lakeside offers a perfect escape for relaxation and scenic views. Woodlawn's unique charm makes it an ideal base for your adventure.

  • Chicago: As a vibrant metropolis, Chicago offers an eclectic mix of cultural experiences and urban adventures. Woodlawn is nestled within this bustling city, making it an ideal base for exploration. From iconic shopping districts to world-class arenas and theatres, there’s no shortage of entertainment. Chicago's rich sporting culture is highlighted by its impressive stadiums, while urban parks provide serene retreats amidst the cityscape. Whether you're visiting in the summer for family outings or in the quieter winter months, Chicago guarantees a memorable city-themed experience.
  • Hyde Park: Located a mere mile from Woodlawn, Hyde Park is a charming neighbourhood known for its cultural richness and family-friendly atmosphere. This area is home to historic institutions, including renowned colleges, which add to its educational allure. Visitors can enjoy leisurely strolls in its beautiful urban parks or partake in various events at local conference venues. With a vibrant shopping scene and access to entertainment facilities, Hyde Park offers a delightful blend of culture and community, making it a perfect spot for exploration.
  • Washington Park: Also located just 1.6km from Woodlawn, Washington Park is a neighbourhood that thrives on its cultural heritage and family-oriented activities. This area is an educational hub with its historic college and university presence. Visitors can engage in diverse shopping experiences while enjoying the local arena entertainment. The expansive urban park and sports facilities nearby provide ample opportunities for outdoor activities. Washington Park stands out as a cultural gem, perfect for those seeking a city-themed getaway.

Things to do near Woodlawn

Woodlawn offers an enriching experience for culture enthusiasts and families alike, featuring educational sites, an arena for entertainment, and vibrant shopping areas. Visitors can enjoy outdoor adventures, perfect for family outings or even dream weddings. Explore the unique charm of Woodlawn and immerse yourself in its community spirit, making it an ideal destination for a memorable vacation.

Shopping

City Market, located 11.3km from Woodlawn, offers a vibrant public market atmosphere perfect for unique gifts. Harry Potter Shop Chicago, 12.9km away, caters to families with its magical merchandise. For a traditional shopping centre experience, visit Chicago Place Mall, also 12.9km distant, featuring a variety of shops.

Recreation

Soldier Field, merely 9.7km from Woodlawn, offers a vibrant atmosphere with exciting sports events. For a more tranquil experience, visit Northerly Island Natural Area, located 8.0km away, where you can unwind amidst nature and enjoy peaceful surroundings.

Adventure

Embark on an adventure at Salt Creek Trail, 19.3km from Woodlawn, where you can enjoy picturesque hiking amidst nature. For a splash of fun, visit Rainbow Falls Waterpark, 40.2km away, or Deep River Water Park, 46.7km away, both offering thrilling rides and family entertainment.

Nightlife

In Woodlawn, the Huntington Bank Pavilion at Northerly Island offers romantic theatre experiences, while Film Row Cinema provides family-friendly films. For a more adventurous night, the Amazing Chicago's Funhouse Maze is perfect for families seeking excitement, all within a short distance from the neighbourhood.

*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 between December and February when accommodation prices are lower, especially on Mondays. Avoid Saturdays for the best rates. Use Expedia to refine your search by budget and accommodation type, and filter for eco-certified options. For greater savings, combine your hotel booking with flights and activities in an Expedia package. Additionally, make use of public transport to navigate the area affordably, and explore free local attractions to enhance your experience without overspending.

  • 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, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and offers, simply sort the price filter from low to high.
  • Consider bundling your trip: You can enjoy significant savings by combining your Woodlawn hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Woodlawn

Woodlawn offers a delightful blend of culture, family activities, and outdoor adventures. Visitors can explore urban parks, historic houses, and nearby beaches, making it an ideal destination for those seeking a vibrant city experience. Don't miss the chance to visit Woodlawn Hospital and Woodlawn Park for a taste of local life. Whether you're enjoying leisurely strolls or immersing yourself in history, Woodlawn has something for everyone.

  • McCormick Place: Located 8.0km from Woodlawn, McCormick Place is a premier event and conference venue that exudes a professional atmosphere. It hosts a variety of trade shows and conventions, making it a hub for business and networking opportunities.
  • Chicago Museum of Science and Industry: Just 3.2km away, this science museum offers a captivating experience for families and culture enthusiasts alike. Interactive exhibits and fascinating displays make science accessible and enjoyable for all ages.
  • Field Museum of Natural History: Situated 9.7km from Woodlawn, the Field Museum immerses visitors in natural history and culture. With impressive collections, including Sue the T. rex, it’s a delightful destination for families and those interested in the wonders of our planet.

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

Travelling to Woodlawn, Chicago is convenient with three major airports. Chicago O'Hare International Airport (ORD) is situated 32.2km away, with excellent hotel options including 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), located 11.3km away, offers luxurious stays at The Langham and Nobu Hotel, both 8-14.5km from the airport. For those flying into Chicago Executive Airport (PWK), 45.1km from Woodlawn, notable hotels include the 4-star Hilton Chicago/Northbrook, just 1.6km away, ensuring easy access to your destination.

Explore a world of travel with Expedia

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.
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.