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

Price found within the past 48 hours. Click for updated prices.
HYATT house Chicago/Schaumburg
LondonHouse Chicago, Curio Collection by Hilton
Renaissance Chicago Downtown Hotel
citizenM Chicago Downtown
La Banque Hotel

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
$169 nightly
The price is $199 total per night from Aug 10 to Aug 11
$199 total
Aug 10 - Aug 11
Total includes taxes and fees
7.8/10 Good! (8,865 reviews)
"It is a historic place"

Reviewed on Jul 18, 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
$301 nightly
The price is $348 total per night from Aug 19 to Aug 20
$348 total
Aug 19 - Aug 20
Total includes taxes and fees
9/10 Wonderful! (2,064 reviews)
"Convenient"

Reviewed on Jul 17, 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
$144 nightly
The price is $169 total per night from Aug 17 to Aug 18
$169 total
Aug 17 - Aug 18
Total includes taxes and fees
8.8/10 Excellent! (2,474 reviews)
"Rocky was awesome and gave us great recommendations. Check in lady was nice and had no issues. Only issue we had was the bar. My husband waiting a good 30 min with no acknowledgment and it wasn’t busy. This happened 2 nights in a row. Someone from the food area noticed he hadn’t been helped and helped ..."

Reviewed on Jul 18, 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.