Kenwood Vacations from $193

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $341, price is now $193 per person
$193
per person
Dec 13 - Dec 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,137 reviews)
Rooms were clean and staff was very nice

Reviewed on Oct 18, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,004, price is now $473 per person
$473
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $442, price is now $251 per person
$251
per person
Dec 13 - Dec 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Staff was amazing very help

Reviewed on Oct 17, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,059, price is now $622 per person
$622
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on Oct 15, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $835, price is now $495 per person
$495
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,452 reviews)
"The hotel overall was great! The only negative thing I wish was better is the bed. It was extremely hard and not comfortable to sleep on."

Reviewed on Oct 17, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Nov 10 to Nov 11
$100 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,485 reviews)
"Great location. Close to everything. Clean room. My husband and I got complimentary breakfasts. Thank you, Staff, who were friendly and helpful."

Reviewed on Oct 16, 2025

Freehand Chicago
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
$111 nightly
The price is $130 total per night from Nov 16 to Nov 17
$130 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,123 reviews)
"Overall good"

Reviewed on Oct 17, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,429 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

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

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 acclaimed art scene in this vibrant area.

Elijah Muhammad House

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% 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.