Kenwood Vacations from $345

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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.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,755 reviews)
The hotel was located close to the places we wanted to visit. Plus, it's pick up and drop off for car services was great

Reviewed on Jul 7, 2025

Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District

3.5 out of 5
Near West Side
Save 100% on your flight
per person
Aug 26 - Aug 31
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,036 reviews)
The history of this property alone is amazing. The proximity to the hospital has been wonderful for us as we are here for a clinical trial.

Reviewed on Jul 7, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
It was a very nice hotel. The full buffet breakfast was a definite plus!!

Reviewed on Jul 7, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Nice hotel, restaurant and rooftop bar were lovely. Very nice room and staff as well.

Reviewed on Jul 7, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
The hotel overall was great.

Reviewed on Jul 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
$170 nightly
The price is $200 total per night from Jul 13 to Jul 14
$200 total
Jul 13 - Jul 14
Total includes taxes and fees
7.8/10 Good! (8,887 reviews)
"Everything was great loved the lication"

Reviewed on Jul 6, 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
$243 nightly
The price is $280 total per night from Aug 7 to Aug 8
$280 total
Aug 7 - Aug 8
Total includes taxes and fees
9/10 Wonderful! (1,998 reviews)
"The property is next to most restaurants, shopping mall and walking distance to Navy Pier"

Reviewed on Jul 7, 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
$186 nightly
The price is $218 total per night from Jul 10 to Jul 11
$218 total
Jul 10 - Jul 11
Total includes taxes and fees
8.8/10 Excellent! (2,406 reviews)
"Excellent location. Only one block away from the lake as well as from the Michigan avenue (shopping area). Our room was nice and clean. I should not say room, it was like an one bedroom apartment without a kitchen. The management was very nice."

Reviewed on Jul 8, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,360 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 fascinating museums.

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

River tour boat in Chicago

Architecture River Tour

$49
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.