Kenwood Vacations from $454
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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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $677, price is now $454 per person
$454
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Room clean, staff amazing. Old, tired property.
Reviewed on Jun 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,036, price is now $691 per person
$691
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
This hotel was perfect for 4 days in Chicago to explore. Walking distance to many shops, restaurants and attractions. The included breakfast was an added bonus and the rooftop bar was great! Staff here were always so pleasant and helpful being quick to take your bags, press the button for the elevator and helping with checking in quickly and using the express checkout; never did we have to wait or ask for assistance. The room was perfect (clean, spacious) and had everything we needed. Would definitely stay again and recommend it to others.
Reviewed on Jun 30, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,100, price is now $749 per person
$749
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
The Pendry is in the heart of everything downtown. The blue line in from the airport was about a 7 minute walk from the lake stop. Rooftop bar is a nice visit as well as the lobby bar. Great staff, good vibes.
Reviewed on Jun 29, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $847, price is now $580 per person
$580
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Room service was terrible other than that I really liked the hotel
Reviewed on Jun 30, 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
5 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
$149 nightly
The price is $177 total per night from Jul 1 to Jul 2
$177 total
Jul 1 - Jul 2
Total with taxes and fees
8/10 Very Good! (10,172 reviews)
"Was a great view but needs a bit of updating! The stairwell door is annoying! Anytime someone would go thru it would pull on our door and wake us from our sleep! AC barely worked. Couldn't do anything with the TV! NO streaming barely see it! At least get a smart TV!"
Reviewed on Jun 30, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 5 to Jul 6
$215 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,820 reviews)
"Room service was terrible other than that I really liked the hotel"
Reviewed on Jun 30, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jul 20 to Jul 21
$154 total
Jul 20 - Jul 21
Total with taxes and fees
8.8/10 Excellent! (2,753 reviews)
"I did not have a good experience. First, I was not told about the $150 deposit until I arrived but okay no problem. The issue was I was double charged for the deposit. I spoke one manager the following morning who did see the double charge she said she would fix it and offered us $100 credit to use ..."
Reviewed on Jun 30, 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
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.