Kenwood Vacations from $270
Book a Hotel + Flight or Car together to unlock savings
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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $440, price is now $270 per person
$270
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,148 reviews)
The bathroom in my room was looking worse for wear, broken tiles and caulk missing.
However the room itself was clean and staff was sooooo helpful and courteous which made my stay great! I even was out of body wash and the girl at the front desk made sure I got some after house keeping didn’t bring any after an hour and I wanted to shower.
Good people working here!
Reviewed on Oct 28, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $615, price is now $329 per person
$329
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Great location, nice rooms, nice rooftop bar and large breakfast buffet included.
Reviewed on Oct 28, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $503, price is now $294 per person
$294
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
We stayed 3 nights. The hotel has two elevators. Each was out of service at some point; one was out of service an entire day.
The workout room is tiny and lacks much equipment.
Reviewed on Oct 29, 2026
Where to stay in Kenwood
Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
Downtown Chicago
4 out of top 10 points of interest in this area
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
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $129 total per night from Nov 10 to Nov 11
$129 total
Nov 10 - Nov 11
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $159 total per night from Nov 9 to Nov 10
$159 total
Nov 9 - Nov 10
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 23 to Nov 24
$138 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (5,570 reviews)
"The rooms need a deep clean, they were clean but stained on the ceiling and carpets. Bed was very worn. Staff were all very nice, from check in to seeing staff in the elevator!"
Reviewed on Oct 29, 2026
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.
Stay near popular Kenwood attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.