
Kenwood Vacations from $139
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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

theWit Chicago, a Hilton Hotel
Reviewed on Nov 22, 2025


Hilton Grand Vacations Club Chicago Magnificent Mile
Reviewed on Oct 28, 2025

Pendry Chicago
Reviewed on Nov 24, 2025

The Emily Hotel
Reviewed on Nov 22, 2025
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.
Kenwood Hotel Deals

Palmer House a Hilton Hotel
Room great, lobby bar the best! Christmas tree gorgeous. And free brownie a nice touch!
Reviewed on Nov 22, 2025

Embassy Suites by Hilton Chicago Downtown River North
All above.
Reviewed on Nov 24, 2025

Hilton Chicago/Magnificent Mile Suites
Room was clean and spacious!
Reviewed on Nov 23, 2025
Discover the most popular places to visit in Kenwood
4944 S Woodlawn Ave
Find out about the history of Chicago when you spend time 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 when you spend time at Obama's House. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Muddy Waters’ House
Find out about the history of Chicago when you spend time at Muddy Waters’ House. Experience the fascinating museums and acclaimed art scene in this vibrant area.
Things to do

Skydeck - Willis Tower Admission

Chicago: Navy Pier Centennial Wheel Ticket
























