Title: Visit Woodlawn: Best of Woodlawn, Chicago Travel 2026 | Expedia Tourism - Expedia.ca [Hotels in Woodlawn](https://expedia.ca/Woodlawn-Chicago-Hotels.0-n6132422-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Woodlawn Car Rentals](https://expedia.ca/Car-Rentals-In-Woodlawn.d6132422.Car-Rental-Guide)[Woodlawn Vacations](https://expedia.ca/Woodlawn.d6132422.Destination-Travel-Guides) # Woodlawn ## Chicago ![This photo is special because it reflects the beauty of this magnificent city.](https://images.trvl-media.com/place/829/206e02db-61eb-498c-997e-b2e29b57676d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![This photo is special because it reflects the beauty of this magnificent city.](https://images.trvl-media.com/place/829/206e02db-61eb-498c-997e-b2e29b57676d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Woodlawn Things to do Hotels Where to stay [Chicago travel guide](https://expedia.ca/Chicago.dx178248) --- ### Popular places to visit ![The Museum of Science and Industry has a huge exhibit dedicated to the actual U-505—the only German submarine in the United States. On June 4, 1944, a German submarine known as U-505 was prowling off the coast of West Africa on a hunt for American and Allied ships, when depth charges from the USS Chatelain blasted the dreaded U-boat out of hiding. ](https://images.trvl-media.com/place/829/9410af42-b723-4c44-9826-acac99252d47.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Jackson Park Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene. [](https://expedia.ca/Jackson-Park-Woodlawn.d507388.Vacation-Attraction) ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue 4.5/5(19 reviews) You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Wrigley Field featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 4.5/5(158 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![McCormick Place showing a high rise building and a city](https://images.trvl-media.com/place/6069191/6dd1da52-961b-4d36-a030-f105009f678b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### McCormick Place 4.5/5(141 reviews) Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges. [](https://expedia.ca/McCormick-Place-Near-South-Side.d6069191.Vacation-Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4.5/5(459 reviews) A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ![Millennium Park featuring autumn colours, street scenes and a city](https://images.trvl-media.com/place/6069201/87d76a1e-e63f-48a2-8892-fb54ee86f8e1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Millennium Park 4.5/5(722 reviews) A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape. [](https://expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) ### Things to do ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting CA $49 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Chicago: City Minibus Tour with Optional Architecture Cruise](https://mediaim.expedia.com/localexpert/4556313/67d8adf7-64e5-458d-bd4c-e2cc830c3f09.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: City Minibus Tour with Optional Architecture Cruise CA $67 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-city-minibus-tour-with-optional-architecture-cruise.a4556313.activity-details) ![Chicago: Architecture Center Exhibit Admission](https://mediaim.expedia.com/localexpert/4568241/5f6e21b6-651d-45ff-866b-b0d251c892a0.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Architecture Center Exhibit Admission CA $21 per traveller [](https://expedia.ca/things-to-do/chicago-architecture-center-exhibit-admission.a4568241.activity-details) ![Chicago Riverwalk Architecture Walking Tour and Discover Skyline](https://mediaim.expedia.com/localexpert/50714488/bf392116-9915-4d4c-8879-8540fa2d157f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Riverwalk Architecture Walking Tour and Discover Skyline CA $67 per adult [](https://expedia.ca/things-to-do/chicago-riverwalk-architecture-walking-tour-and-discover-skyline.a50714488.activity-details) [See all activities in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) --- ## Woodlawn Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL CA $126 CA $147 total Jan 22 - Jan 23 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ... 8/10 Very Good! (9,799 reviews) Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ... Reviewed on Jan 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132422) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL CA $180 CA $252 total Feb 1 - Feb 2 includes taxes & fees Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ... 8.4/10 Very Good! (2,555 reviews) Did not have breakfast Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=6132422) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL CA $146 CA $172 total Feb 9 - Feb 10 includes taxes & fees Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ... 8.4/10 Very Good! (5,575 reviews) The staff were great! The room was pretty clean. The breakfast was amazing and, the kids loved to pool. The only issue we had was the elevator wait times. As that they were busy it made for long elevator wait times. Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132422) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Royal Sonesta Chicago Downtown 71 E Wacker Dr Chicago IL CA $162 CA $235 total Feb 5 - Feb 6 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ... 9.2/10 Wonderful! (3,259 reviews) Everything is good Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=17543&PinnedHotelID=17543&HadPinnedHotel=true®ionId=6132422) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### River Hotel 75 East Wacker Drive Chicago IL CA $110 CA $129 total Jan 30 - Jan 31 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ... 8.6/10 Excellent! (4,915 reviews) Very good service Reviewed on Jan 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F01%2F2026&endDate=31%2F01%2F2026&selected=2675313&PinnedHotelID=2675313&HadPinnedHotel=true®ionId=6132422) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Chicago - Magnificent Mile 300 E Ohio St Chicago IL CA $118 CA $138 total Feb 1 - Feb 2 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ... 8.6/10 Excellent! (2,255 reviews) My family and I had a great stay! Friendly reception, greeted with warm cookies and water upon arrival. Room was nice and quiet. Enjoyed breakfast at hotel in the morning (not included, extra charge). Location is just a few blocks to magnificent mile. Overall great stay! Reviewed on Jan 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=21152&PinnedHotelID=21152&HadPinnedHotel=true®ionId=6132422) [See all 4,644 properties in Woodlawn](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=22%2F01%2F2026&endDate=23%2F01%2F2026®ionId=6132422) 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. ## Check Woodlawn hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=2026-01-21&endDate=2026-01-22)[Jan 21 - Jan 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=2026-01-21&endDate=2026-01-22) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=2026-01-22&endDate=2026-01-23)[Jan 22 - Jan 23](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=2026-01-22&endDate=2026-01-23) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026)[Jan 23 - Jan 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026)[Jan 30 - Feb 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132422&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026) --- ### Other neighbourhoods around Woodlawn ![Chicago_NearSouthSide_6132399_02](https://images.trvl-media.com/place/6132399/bed0102f-0e70-4cb1-8baa-b00fec33aaca.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Near South Side Travelers choose Near South Side for its abundant dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field. [](https://expedia.ca/Chicago-Near-South-Side.dx6132399) ![South Loop which includes a high-rise building and a city](https://images.trvl-media.com/place/6130108/f1bd0360-1400-4c1c-882e-1779972b657f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### South Loop 4/5(31 area reviews) Known for its fascinating museums, panoramic lake views, and popular shops, there's plenty to explore in South Loop. Top attractions like Soldier Field and Lake Michigan are major draws. Catch the metro at Roosevelt Station or Cermak-McCormick Place Station to see more of the city. [](https://expedia.ca/Chicago-South-Loop.dx6130108) ![Beautiful fireworks](https://images.trvl-media.com/place/829/1a8abde0-c15d-4b25-9c4c-74d2678f7428.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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). [](https://expedia.ca/Chicago-Theatre-District.dx651190586167894016) ![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(725 area reviews) 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. [](https://expedia.ca/Chicago-The-Loop.dx800024) ![A view of the Chicago skyline from the rooftop of the Ace Hotel in the West Loop.](https://images.trvl-media.com/place/829/1a47d60f-edf5-4e44-b25c-6a3708851864.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Near West Side 4/5(29 area reviews) Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town. [](https://expedia.ca/Chicago-Near-West-Side.dx6132434) ![Downtown Chicago showing a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699) --- --- - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Woodlawn ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app