Kenwood Vacations from $233

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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 - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Save 100% on your flight
Price was $359, price is now $233 per person
$233
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (999 reviews)
Staff was very courteous however the hotel needs to be updated. One little tiny bar of soap in the room was rather skimpy.

Reviewed on Jan 11, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was $1,825, price is now $935 per person
$935
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,006, price is now $563 per person
$563
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on Jan 8, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $326 per person
$326
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, comfortable and quiet.

Reviewed on Jan 30, 2026

Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Save 100% on your flight
Price was $365, price is now $236 per person
$236
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago

Reviewed on Nov 7, 2025

Where to stay in Kenwood

Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
Downtown Chicago showing a city

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.

Find hotels in Downtown Chicago

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
$97 nightly
The price is $114 total per night from Feb 1 to Feb 2
$114 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (9,826 reviews)
Awesome location

Reviewed on Jan 30, 2026

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $120 total per night from Feb 8 to Feb 9
$120 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (5,617 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.

Reviewed on Jan 28, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $156 total per night from Feb 9 to Feb 10
$156 total
Feb 9 - Feb 10
Total with taxes and fees
9.2/10 Wonderful! (3,258 reviews)
Room was clean, comfortable and quiet.

Reviewed on Jan 30, 2026

Hotel Riu Plaza Chicago
See all 4,752 properties in Kenwood
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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.

4944 S Woodlawn Ave

Obama's House

5/5(2 reviews)

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 acclaimed theater scene.

Obama's House

Elijah Muhammad House

Find out about the history of Chicago when you take a trip to Elijah Muhammad House. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Elijah Muhammad House

Things to do

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Color Factory Chicago Ticket

Color Factory Chicago Ticket

$34
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.