Kenwood Vacations from $319

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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 O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,094 reviews)
Shower door was off track. Had to struggle with it to gain entry to the shower. Overall, great experienc. Staff was excellent

Reviewed on Jul 13, 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,066 reviews)
Bathroom tile was loose and shower grout sisnr look to clean.

Reviewed on Jul 13, 2025

Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
8.4/10 Very Good! (999 reviews)
Very disappointed with the lack of dining options and the fact that there’s no complimentary coffee or water available in the lobby. We will not stay here again

Reviewed on Jun 10, 2025

HYATT house Chicago/Schaumburg

HYATT house Chicago/Schaumburg

3.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 20
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.8/10 Good! (1,003 reviews)
Wasn’t as nice as I thought it would be. Very plain. Needs a lot of updating. It is clean though.

Reviewed on Jun 6, 2025

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,000 reviews)
Clean, great location .

Reviewed on Jul 12, 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
$179 nightly
The price is $210 total per night from Jul 27 to Jul 28
$210 total
Jul 27 - Jul 28
Total includes taxes and fees
7.8/10 Good! (8,941 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 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
$231 nightly
The price is $266 total per night from Aug 10 to Aug 11
$266 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (2,029 reviews)
"Clean, great location ."

Reviewed on Jul 12, 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
$151 nightly
The price is $178 total per night from Aug 10 to Aug 11
$178 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (2,425 reviews)
"Great location and rooms are spacious and clean."

Reviewed on Jul 11, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,372 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

$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.