Woodlawn
Chicago
Visit Woodlawn
Stay near popular Woodlawn attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Woodlawn Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
The price is CA $213 per night from Sep 27 to Sep 28
CA $213
CA $254 total
Sep 27 - Sep 28
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The price is CA $223 per night from Sep 28 to Sep 29
CA $223
CA $265 total
Sep 28 - Sep 29
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 helpful ...
8/10 Very good! (2,230 reviews)
"Nice location, clean spacious room, comfortable bed all of the things you would expect were there My only issue was a lack of electrical outlets next to the bed. In today world there should be an available outlet or two next to the bed"
Reviewed on Sep 13, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $220 per night from Sep 27 to Sep 28
CA $220
CA $262 total
Sep 27 - Sep 28
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! (10,231 reviews)
"The attendant, Steve, was extremely helpful but the front desk, various individuals were both uninformed, and unhelpful. The stairs between the lobby and the fourth floor looked horrifyingly filthy with litter and debris. That area should not be avilable to guests if theyre not going to pay attention ..."
Reviewed on Sep 13, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
The price is CA $302 per night from Sep 25 to Sep 26
CA $302
CA $401 total
Sep 25 - Sep 26
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 ...
8.6/10 Excellent! (3,191 reviews)
"Excellent hotel. Very clean, modern, friendly staff and great location"
Reviewed on Sep 13, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
The price is CA $167 per night from Sep 20 to Sep 21
CA $167
CA $199 total
Sep 20 - Sep 21
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
The price is CA $429 per night from Sep 27 to Sep 28
CA $429
CA $559 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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 and neighborhoods for the activities you enjoy most.
Downtown Chicago
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Photo by © City of Chicago
Open Photo by © City of Chicago
Magnificent Mile
Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.
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.
