Kenwood Vacations from $300

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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

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
Hotel Felix River North/Magnificent Mile
Hilton Garden Inn Chicago Downtown South Loop
Fairmont Chicago at Millennium Park
LondonHouse Chicago, Curio Collection by Hilton

Where to stay in Kenwood

Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood

Kenwood Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Aug 5 to Aug 6
$168 total
Aug 5 - Aug 6
Total includes taxes and fees
7.8/10 Good! (8,887 reviews)
"Everything was great loved the lication"

Reviewed on Jul 6, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
$291 nightly
The price is $336 total per night from Aug 7 to Aug 8
$336 total
Aug 7 - Aug 8
Total includes taxes and fees
9/10 Wonderful! (1,978 reviews)
"Great hotel."

Reviewed on Jul 5, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $199 total per night from Jul 10 to Jul 11
$199 total
Jul 10 - Jul 11
Total includes taxes and fees
8.8/10 Excellent! (2,392 reviews)
"A complimentary breakfast is a recommendation"

Reviewed on Jul 6, 2025

Hilton Chicago/Magnificent Mile Suites
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.

Discover the most popular places to visit in Kenwood

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.