
Kenwood Holidays from £1,401
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Kenwood Holiday
Whether you're coming for its history or walking, the neighbourhood of Kenwood has plenty to keep you entertained. Discover all of this and more with ease by booking a Kenwood holiday package. When it's time to see the sights, you'll find a lot of awesome attractions nearby including University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. Visit one, two or more during your trip to Kenwood. Whatever your travel plans or the size of your budget, booking your perfect Kenwood holiday is simple with Expedia.

Hotel Felix River North/Magnificent Mile
Reviewed on 30 Aug 2026

Hotel Riu Plaza Chicago
Reviewed on 30 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on 30 Aug 2026

Four Seasons Hotel Chicago
Reviewed on 30 Aug 2026

Silversmith Hotel Chicago Downtown
Reviewed on 30 Aug 2026
Where to stay in Kenwood

Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Kenwood

Congress Plaza Hotel
"Staff were all very nice. The hotel is a beautiful historic building, however, it has not been maintained. Our room was clean, but small and the air conditioner didn’t work well. For the price, this wasn’t worth it."
Reviewed on 30 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast

Kasa Magnificent Mile Chicago
"Love the layout. Great location. Super easy check in and check out"
Reviewed on 30 Aug 2026
Frequently asked questions
Why should I book my Kenwood holiday with Expedia?
What are the top hotels for my holiday in Kenwood?
How do I get a cheap holiday to Kenwood?
What should I do on my Kenwood holiday?
What is the best area to stay in when on holiday in Kenwood?
Do I need a visa for my Kenwood holiday?
What should I wear on my Kenwood holiday?
What does an Expedia Kenwood holiday include?
Does Expedia offer Book Now, Pay Later Kenwood holidays?
- Pay monthly holidays: Klarna offers the ability to pay in multiple instalments that work for all budget sizes, so you can have that well-deserved holiday sooner.
- No-deposit holidays: If not paying upfront for your trip makes hitting that "book now" button easier, choose a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Kenwood Expedia holiday?
Stay near popular Kenwood attractions
Barack Obama Residence
49th Street Beach
Hyde Park Art Center
Little Black Pearl Academy
Muddy Waters’ House
Jessie 'Ma' Houston Park
Kam Isaiah Israel Congregation
Rainbow-PUSH Headquarters
Things to do

Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Navy Pier Centennial Wheel Ticket
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.










