
Kenwood Vacations from $387
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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




citizenM Chicago Downtown
Reviewed on Jul 18, 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

Congress Plaza Hotel
Reviewed on Jul 18, 2025

InterContinental Chicago Magnificent Mile by IHG
Reviewed on Jul 17, 2025

Hilton Chicago/Magnificent Mile Suites
Reviewed on Jul 18, 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 fascinating museums.
Muddy Waters’ House
Find out about the history of Chicago when you spend time at Muddy Waters’ House. Experience the acclaimed art scene and fascinating museums in this vibrant area.
Things to do

Wendella's 90-min Chicago River Architecture Tour
