Woodlawn
Chicago
Visit Woodlawn
Stay near popular Woodlawn attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
S$32
per adult
88% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
S$199
per adult
82% of travellers recommend
Chicago Crime and Mob Bus Tour
S$63
per adult
90% of travellers recommend
Top hotels in Woodlawn
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
The price is S$249 per night from 3 Aug to 4 Aug
S$249
3 Aug - 4 Aug
includes taxes & fees
Stay at this business-friendly hotel in Rosemont. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.8/10 Excellent! (2,839 reviews)
"Clean rooms nice hotel"
Reviewed on 14 Jul, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The price is S$252 per night from 27 Jul to 28 Jul
S$252
27 Jul - 28 Jul
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff ...
8.2/10 Very good! (1,746 reviews)
"The property is located near the beach and restaurants. It’s ideal for accessibility. Unfortunately our hotel room shower was broken. The bathroom was in poor condition and had not been maintained."
Reviewed on 13 Jul, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
The price is S$405 per night from 26 Jul to 27 Jul
S$405
26 Jul - 27 Jul
includes taxes & fees
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,917 reviews)
"While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that ..."
Reviewed on 13 Jul, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is S$291 per night from 10 Aug to 11 Aug
S$291
10 Aug - 11 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very good! (10,257 reviews)
"Poor signage"
Reviewed on 14 Jul, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is S$337 per night from 9 Aug to 10 Aug
S$337
9 Aug - 10 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free Wi-Fi and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk ...
9.4/10 Exceptional! (4,698 reviews)
"It was very clean and the staff was so friendly and helpful, breakfast was also"
Reviewed on 14 Jul, 2026
River Hotel
75 East Wacker Drive Chicago IL
The price is S$288 per night from 9 Aug to 10 Aug
S$288
9 Aug - 10 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, room service and a fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (5,351 reviews)
"Room is small but clean enough. Location is the best. Close to the ruyand almost every thing else."
Reviewed on 13 Jul, 2026
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. Learn more about Woodlawn
Learn more about 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.
Magnificent Mile
Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.
The Loop
Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.
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
Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
Woodlawn
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- Visit Bellwood
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- Visit Magnificent Mile
- Visit Morgan Park
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- Visit South Loop
- Visit The Loop
- Visit West Lawn
- Visit West Loop Gate
- Visit West Loop
- Visit West Town
- Visit Winchester-Hood Garden Homes
- Visit Chicago
- Visit Crestwood
- Visit Dolton
- Grant Park
- Mccormick Place
- Visit Melrose Park
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- Visit South Side
- University of Illinois Chicago
