Woodlawn Vacations
Book a Hotel + Flight together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AED 148 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Woodlawn
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.
Woodlawn Hotel Deals
Hilton Chicago
Best option for us while attending an event at McCormick place, with ability to park in public parking that is cheaper than the hotel parking!
Reviewed on 30 December 2025
Hilton Chicago/Magnificent Mile Suites
Clean room , great location.
Reviewed on 30 December 2025
Palmer House a Hilton Hotel
Our stay was absolutely perfect. The room was clean. The staff was amazing! The decorations were festive and the pool was spotless warm and very very family friendly!!
Reviewed on 29 December 2025
Discover the most popular places to visit in Woodlawn
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 fascinating museums.
Michigan Avenue
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.
Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.