Kenwood Vacations from $387

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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.
HYATT house Chicago/Schaumburg

HYATT house Chicago/Schaumburg

3.5 out of 5
Save 100% on your flight
per person
Sep 28 - Oct 4
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
7.8/10 Good! (1,002 reviews)
The staff was very nice and friendly!

Reviewed on Jul 16, 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 19 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
Staff was super helpful.

Reviewed on Jul 17, 2025

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Property was updated and in a great central location in downtown.

Reviewed on Jul 16, 2025

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,315 reviews)
Excellent room in great location. Really nice and high tech facility. Definitely will use again.

Reviewed on Jul 18, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Oct 2 - Oct 5
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (426 reviews)
A great property in a average community

Reviewed on Jun 8, 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
$169 nightly
The price is $199 total per night from Aug 10 to Aug 11
$199 total
Aug 10 - Aug 11
Total includes taxes and fees
7.8/10 Good! (8,865 reviews)
"It is a historic place"

Reviewed on Jul 18, 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
$301 nightly
The price is $348 total per night from Aug 19 to Aug 20
$348 total
Aug 19 - Aug 20
Total includes taxes and fees
9/10 Wonderful! (2,064 reviews)
"Convenient"

Reviewed on Jul 17, 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
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Aug 17 to Aug 18
$169 total
Aug 17 - Aug 18
Total includes taxes and fees
8.8/10 Excellent! (2,474 reviews)
"Rocky was awesome and gave us great recommendations. Check in lady was nice and had no issues. Only issue we had was the bar. My husband waiting a good 30 min with no acknowledgment and it wasn’t busy. This happened 2 nights in a row. Someone from the food area noticed he hadn’t been helped and helped ..."

Reviewed on Jul 18, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,458 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

Muddy Waters’ House

Find out about the history of Chicago when you spend time at Muddy Waters’ House. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Muddy Waters’ House

Things to do

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% 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
94% 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.