Kenwood Holidays from £1,401

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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.

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Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
£1,401
per person
7 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (2,960 reviews)
The staff was easily the best part of my stay at Hotel Felix. Everyone I interacted with was incredibly kind, accommodating, and helpful. The staff who assisted me with check-in and anything else I needed during my stay were wonderful, housekeeping was great, and overall the customer service was consistently warm and pleasant. I also appreciated that the hotel had breakfast available for purchase on-site, along with complimentary coffee and water throughout the day. The lobby is very nice and gives the hotel a polished first impression. Unfortunately, that did not really translate to the room. My room was extremely small and felt more like a shoebox with a bathroom attached. There was no closet, no refrigerator, and very little space overall. The robe folded in the bathroom had a visible stain on the collar, and there were stains on the ceiling as well. The biggest issue for me was the noise. I could hear people opening, closing, locking, and slamming doors throughout the hallway very clearly. On multiple nights it actually woke me out of my sleep because the sound was so close and abrupt that it made me think someone was trying to enter my room. I’m not sure whether that comes down to thin walls, limited soundproofing, or the way the doors are designed, but it was definitely disruptive. Overall, the hotel did what I needed it to do: it gave me somewhere to put my things and sleep at night. If you’re traveling and just need a very basic place to stay, it gets the job d

Reviewed on 30 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,661
per person
7 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Lobby smelt amazing right off the bat. All the staff everywhere were very helpful. Breakfast was very good with lots of options. Room was clean and very nice! I definitely recommend!

Reviewed on 30 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
£1,540
per person
7 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
Everything was perfect, they let me check in early. The staff was amazing.

Reviewed on 30 Aug 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,877
per person
7 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable

Reviewed on 30 Aug 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
Save 100% on your flight
£1,797
per person
7 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
Spacious room. We were on the ninth floor and could barely hear the L train. It sounded like an AC unit turning on for a few moments.

Reviewed on 30 Aug 2026

Where to stay in Kenwood

Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

A river with yellow boats, a bridge, and tall buildings.

The Loop

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

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

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

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A wooden pavilion with a view of a city skyline and a body of water.

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

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£92
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,233 reviews)
"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

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£126
7 Sept - 8 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL
9.4/10 Exceptional! (882 reviews)
"Love the layout. Great location. Super easy check in and check out"

Reviewed on 30 Aug 2026

Get rates
Kasa Magnificent Mile Chicago
See all 4,384 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.

Frequently asked questions

Why should I book my Kenwood holiday with Expedia?
With great-value flights, accommodation and car hire options all in one convenient place, Expedia makes arranging your Kenwood adventure a piece of cake. Moreover, we can help you bundle your bookings into a package holiday so you can get even more savings. Pick from fabulous escapes, add flights and/or a hire car (and maybe also some fun tours and activities!) and get unbeatable prices. Need to cancel? Expedia offers a flexible cancellation policy for many reservations. To learn more, head over to our Customer Service Portal link.
What are the top hotels for my holiday in Kenwood?
If you're hoping to stay close to Kenwood, make a reservation at Best Western Plus Hyde Park Chicago Hotel or Chicago Lake Shore Hotel. Both offer comfortable beds and are top options with lots of travellers.
How do I get a cheap holiday to Kenwood?
One of the simplest ways to save pounds (and time) is to combine your bookings with Expedia. Flights, hotels, activities and hire cars — we've got them all. Select a combination that best fits you and see your savings pile up. We know holidays are never one-size-fits-all. That's why we offer over 400 partner airlines and 321,000 hotel options across the world, which lets you customise your Kenwood holiday your way. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Kenwood holiday?
There are lots of things to keep you busy while on a holiday in Kenwood. University of Chicago, Chicago Museum of Science and Industry, Guaranteed Rate Field and State Street are a few of this city's leading attractions.
What is the best area to stay in when on holiday in Kenwood?
If you'll be visiting 4944 S Woodlawn Ave, maximise your time sightseeing and find a place to stay nearby. It's one of the top attractions in Kenwood.
Do I need a visa for my Kenwood holiday?
Visa requirements for Kenwood vary depending on your nationality and reason for your visit. Check official government websites to determine if you need a visa for your holiday. Here you'll also find the most up-to-date information, including details about application procedures or supporting documentation you might need. Research your visa requirements well in advance to ensure a travel experience that's hassle free. Also check to see that your passport is valid for a further six months from your return date.
What should I wear on my Kenwood holiday?
First, consider the sorts of activities you have planned during your holiday in Kenwood and travel with pieces that can be mixed and matched. For fashion inspiration or information on any dress codes, browse style blogs or social media accounts.
What does an Expedia Kenwood holiday include?
Expedia has everything you need to plan your Kenwood trip, but what your package looks like is totally up to you. Pick from any combination of flights, hotels and hire cars. In search of some activities or tours to keep you busy? Once you've made your booking, you can add them too. Whatever your budget or style, there's a package to suit your needs. Expedia has many property types, with the most favoured in Kenwood being apartments and private holiday homes. Whatever escape you prefer, Expedia gives you the flexibility and freedom to tailor your holiday to suit your needs.
Does Expedia offer Book Now, Pay Later Kenwood holidays?
We sure do. Expedia has partnered with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Make sure you bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:
  • 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?
Most definitely. Expedia has more than 400 partner airlines to pick from around the globe. With so much choice, finding the right carrier to get you to Kenwood shouldn't be hard.

Stay near popular Kenwood attractions

Barack Obama Residence

You can find out about the history of Chicago with a stop at Barack Obama Residence. Stroll along the beautiful beaches in this family-friendly area or visit its top-notch restaurants.
See properties

49th Street Beach

Why not spend a lazy afternoon at 49th Street Beach during your trip to Chicago? Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
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Hyde Park Art Center

Enjoy an outing to Hyde Park Art Center during your stay in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
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Little Black Pearl Academy

Walk around the campus at Little Black Pearl Academy during your stay in Chicago. Wander through the lakeside and beautiful beaches in this family-friendly area.
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Muddy Waters’ House

Find out about the history of Chicago when you spend time at Muddy Waters’ House. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
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Jessie 'Ma' Houston Park

You can take time to visit Jessie 'Ma' Houston Park during your travels to Chicago. Wander through the lakeside and beautiful beaches in this family-friendly area.
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Kam Isaiah Israel Congregation

You can find out about the history of Chicago when you stop by Kam Isaiah Israel Congregation. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
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Rainbow-PUSH Headquarters

Learn about the local history of Chicago when you take a trip to Rainbow-PUSH Headquarters. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% 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. Flight-inclusive packages are ATOL protected.