Popular places to visit
4944 S Woodlawn Ave
Find out about the history of Chicago with a stop at 4944 S Woodlawn Ave. Stroll along the lakeside or visit the notable monuments in this vibrant area.
Obama's House
Find out about the history of Chicago with a stop at Obama's House. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Hyde Park Art Center
You can spend time browsing the exhibits at Hyde Park Art Center during your travels in Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
Barack Obama Residence
You can find out about the history of Chicago with a stop at Barack Obama Residence. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.
49th Street Beach
Why not spend a lazy afternoon at 49th Street Beach during your trip to Chicago? Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Little Black Pearl Academy
Walk around the campus at Little Black Pearl Academy during your stay in Chicago. Wander through the lakeside and beautiful beaches in this family-friendly area.
Things to do
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Ticket
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Top hotels in Kenwood
Embassy Suites by Hilton Chicago Downtown River North
Great place always.
Reviewed on 12 Dec 2025
Hilton Chicago/Magnificent Mile Suites
Pleasant staff, clean and spacious rooms. Excellent centralized location to many restaurants and things to do in Chicago that are both accessible by train and on foot. Definitely one of my new go to stays in the city.
Reviewed on 9 Dec 2025
Silversmith Hotel Chicago Downtown
The staff is so friendly and helpful. We now have stayed here twice and enjoy the hotel.
Reviewed on 11 Dec 2025
Palmer House a Hilton Hotel
Beautiful hotel with excellent service
Reviewed on 11 Dec 2025
Eurostars Magnificent Mile
The room was clean, had the best massage at the spa, and enjoyed the brunch at the restaurant downstairs. It was a great stay. I’ll likely be back!
Reviewed on 8 Dec 2025
Club Quarters Hotel Wacker at Michigan, Chicago
The room was beautiful the stay was amazing
Reviewed on 11 Dec 2025
Other neighbourhoods around Kenwood
Near South Side
Travellers choose Near South Side for its ample dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
South Loop
Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
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.
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.
West Loop
Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
