Kenwood Vacations from $525

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $790, price is now $525 per person
$525
per person
May 12 - May 15
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Best breakfast buffet I’ve ever had while in Chicago. ALL staff was nice, welcoming and willing to be of assistance. Definitely plan on staying again the next time I’m in Chicago‼️

Reviewed on Mar 29, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,004, price is now $669 per person
$669
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Everything was perfect

Reviewed on Mar 26, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,501, price is now $1,008 per person
$1,008
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Perfect area- close to everything!

Reviewed on Mar 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $963, price is now $655 per person
$655
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 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

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
$110 nightly
The price is $129 total per night from Apr 1 to Apr 2
$129 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (10,014 reviews)
N/A

Reviewed on Mar 30, 2026

Congress Plaza Hotel
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
$122 nightly
The price is $143 total per night from Apr 6 to Apr 7
$143 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (4,019 reviews)
.

Reviewed on Mar 29, 2026

Hilton Chicago/Magnificent Mile Suites
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
$127 nightly
The price is $149 total per night from Apr 12 to Apr 13
$149 total
Apr 12 - Apr 13
Total with taxes and fees
8.6/10 Excellent! (5,799 reviews)
Pretty pricey for what you actually get. Valet is $79 per night on top of room fee. Beds are hard and uncomfortable. The linen on bed was full of stains. The temperature in room is either too hot or too cold. Pool water is disgusting. On the other hand:valet staff was excellent. The location is excellent. ...

Reviewed on Mar 29, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,541 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

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

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

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$66
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
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.