Kenwood Holidays from £1,019
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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.
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
£1,019
per person
2 Dec - 7 Dec
found 17 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
My biggest issue here is the room I was given, 801. Just not a nice room at all. It's tiny, it had a stale odour, no table/chair, its gloomy, its location, it's a bathtub, not a standalone shower, the mechanics of the door.... If I can say one thing, it is that the bed was comfortable and the fixtures in the bathroom look new. It's just not a place you want to spend any time.
The second issue was the length of time to get room service. After many hours of travel, I was too tired to eat out anywhere. I ordered room service and the food was stone cold. The only edible part was the skinny fires that came with the burger. BTW, would be helpful to list the side on the order form as it just said burger... so I ordered separate fries which couldn't be eaten because they were not warm.
Reviewed on 13 Oct 2026
Swissotel - Chicago
Downtown Chicago
£1,206
per person
27 Dec - 2 Jan
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Beautiful location by Chicago river. We used parking with spot hero app and valet was very helpful,in showing us how to get to our parking location. Room was spacious and clean. Beds were comfortable. Staff was helpful
Reviewed on 14 Oct 2026
Where to stay in Kenwood
Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£95
11 Nov - 12 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£136
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
£115
1 Nov - 2 Nov
includes taxes & fees
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
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 art galleries in this vibrant area.
KAM Synagogue
KAM Synagogue is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
Muddy Waters’ House
Find out about the history of Chicago when you spend time at Muddy Waters’ House. Experience the acclaimed art galleries and fascinating museums in this vibrant area.
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.
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.
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.
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.
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 art galleries in this vibrant area.
Things to do
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
* 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.