Kenwood Vacations from $335
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Your Kenwood Vacation
History, walking, food, good times — you'll find all that and more in Kenwood. Experience the very best of this neighborhood with a customized vacation package to Kenwood. Kick off your trip to Kenwood by checking out nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. Whatever your travel goals or the size of your budget, booking the ultimate Kenwood vacation is easy with Expedia.
The Latest Kenwood Vacation Packages
Hotel Saint Clair- Magnificent Mile
Reviewed on Aug 18, 2026
Level Chicago Fulton Market
Reviewed on Aug 17, 2026
Where to stay in Kenwood
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Kenwood Hotel Deals
Congress Plaza Hotel
"The hotel is in a great location right across from Grant Park but the hotel is really dated. I usually love a historic hotel… but this one needs a little love. Our room was “ok”… everything worked and we didn’t have any issues but it was just old and felt old. I wouldn’t stay here again. If you do ..."
Reviewed on Aug 18, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"Very friendly and professional staff. Building does show its age though."
Reviewed on Aug 18, 2026
Kasa Magnificent Mile Chicago
"Loved the check-in and check-out process. Very easy and excellent communication through texts, emails and the Kasa desk in the lobby. The security via the fobs and designated elevators was excellent. The water pressure was good in the shower, and the towels were fluffy. The view in this corner unit ..."
Reviewed on Aug 18, 2026
Stay near popular Kenwood attractions
Obama's House
Barack Obama Residence
Former Home of Muhammad Ali
49th Street Beach
Hyde Park Art Center
Little Black Pearl Academy
Jessie 'Ma' Houston Park
Kam Isaiah Israel Congregation
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
