
Woodlawn Holidays
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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.
Top hotels in Woodlawn

Congress Plaza Hotel
The bartender was fantastic ! All of the staff was amazing ! The rooms “all season “ system was not great because it was 45 degrees Friday night and 80 on Saturday so the room was freezing Friday night and so hot Sunday !!! Other than that the hotel was historically beautiful!!
Reviewed on 27 Mar 2026

Hilton Chicago/Magnificent Mile Suites
Close to everything we wanted to do and the lake and beach
Reviewed on 27 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
We ended up with the stomach bug while we were on vacation, but the staff was all so responsive and helpful to us - allowing a later check-out time and bringing us bleach wipes. The texting feature was very helpful!
Reviewed on 26 Mar 2026
Frequently asked questions
Popular places to visit

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 galleries.

Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.



