Woodlawn
Chicago
Visit Woodlawn
Stay near popular Woodlawn attractions
Things to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
Woodlawn Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $146 per night from Nov 26 to Nov 27
CA $146
CA $174 total
Nov 26 - Nov 27
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 ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The price is CA $188 per night from Nov 9 to Nov 10
CA $188
CA $224 total
Nov 9 - Nov 10
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! (2,611 reviews)
"Bbh"
Reviewed on Oct 28, 2026
River Hotel
75 East Wacker Drive Chicago IL
The price is CA $163 per night from Nov 23 to Nov 24
CA $163
CA $194 total
Nov 23 - Nov 24
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 ...
8.8/10 Excellent! (5,568 reviews)
"Cool old building with a beautiful lobby (retro). Room was skinny, but so is the building. AC was loud in room, but worked well. Bed was ok, but had a big dip in it on one side. Room was very clean and housekeeping cleaned each day, unlike many hotels that do not. View was nice of river, but window ..."
Reviewed on Oct 28, 2026
The Wade
644 N Lake Shore Dr Chicago IL
The price is CA $167 per night from Nov 23 to Nov 24
CA $167
CA $199 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
The price is CA $169 per night from Nov 3 to Nov 4
CA $169
CA $201 total
Nov 3 - Nov 4
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 ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Nov 27 to Nov 28
CA $152
CA $222 total
Nov 27 - Nov 28
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 ...
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.
