Kenwood Vacations from $175

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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 Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $312, price is now $175 per person
$175
per person
Jan 22 - Jan 25
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (1,001 reviews)
Best location to stay

Reviewed on Oct 25, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Price was $637, price is now $310 per person
$310
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (154 reviews)
Beautiful place, friendly staff. We loved the restaurant.

Reviewed on Nov 1, 2025

Sand Hill On The Lake

Sand Hill On The Lake

2 out of 5
Save 100% on your flight
Price was $763, price is now $419 per person
$419
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (77 reviews)
The view on the lake is beautiful and the fireplace made it so cozy during our fall visitl

Reviewed on Nov 10, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $876, price is now $492 per person
$492
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $670, price is now $389 per person
$389
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,771 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.

Reviewed on Nov 14, 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

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
$95 nightly
The price is $112 total per night from Nov 25 to Nov 26
$112 total
Nov 25 - Nov 26
Total with taxes and fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included

Reviewed on Nov 10, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $149 total per night from Nov 24 to Nov 25
$149 total
Nov 24 - Nov 25
Total with taxes and fees
8.4/10 Very Good! (2,060 reviews)
Great location, great staff!

Reviewed on Nov 16, 2025

Palmer House a Hilton 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
$98 nightly
The price is $115 total per night from Dec 7 to Dec 8
$115 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,290 reviews)
I loved that everything was in walking distance. It was very clean. The hospitality service was excellent! Very kind and friendly!

Reviewed on Nov 14, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,581 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 acclaimed art scene.

Obama's House

Muddy Waters’ House

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

Muddy Waters’ 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
98% 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.