Kenwood Holidays from £1,254

Book a Hotel + Flight or Car together to unlock savings

Photo by Marc Jacobs
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to £195 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Packages 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.

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
per person
10 Aug - 17 Aug
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,130 reviews)
Great place to stay. Walkable from south shore train, restaurants and theaters

Reviewed on 19 May 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
We have a plenty staying at this hotel has the best locations and restaurant is so good

Reviewed on 13 May 2024

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,902 reviews)
Beautiful room. Staff was responsive to messaging. Bed was hard. Not much with coffee or creamer. Need a safe in room.

Reviewed on 24 May 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Very nice, clean, large rooms. Well-appointed. Hotel lobby very welcoming. Looked like a lovely outdoor dining patio, though I didn’t eat there.

Reviewed on 22 May 2024

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,138 reviews)
My room was clean and staff friendly.

Reviewed on 21 May 2024

Where to stay in Kenwood

Find the best Kenwood areas and neighborhoods for the activities you enjoy most. Learn more about Kenwood
Downtown Chicago featuring a city

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.

Find hotels in Downtown Chicago

Top hotels in Kenwood

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £127 per night from 27 May to 28 May
£127
per night
27 May - 28 May
7.6/10 Good! (2,598 reviews)
"I don’t really write reviews for places I stay at but this one impressed me beyond my expectations. I planned this trip for my fiancé’s 30th birthday and the location and price of this hotel is the best you will find. Not too far away from everything, conveniently located transportation and so many ..."

Reviewed on 20 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £137 per night from 28 May to 29 May
£137
per night
28 May - 29 May
7.6/10 Good! (6,777 reviews)
"Looks like old antique hotel. It was quiet and felt very safe."

Reviewed on 21 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 27 May to 28 May
£131
per night
27 May - 28 May
8.6/10 Excellent! (2,887 reviews)
"Nice hotel and location"

Reviewed on 20 May 2024

River Hotel
See all 4,027 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Popular places to visit

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

£182
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

£59
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

More trip options

* 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.