Kenwood Holidays from £1,006

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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 Aug - 4 Sept
found 11 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,763 reviews)
Friendly bartender made the whole trip amazing, the beds and bathroom were really nice!

Reviewed on 22 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 Aug - 4 Sept
found 11 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on 1 Jun 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 Aug - 4 Sept
found 11 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Property location was perfect! Rooftop top views was amazing!

Reviewed on 23 Jun 2025

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (1,833 reviews)
The Hotel is physically beautiful. The rooms are spacious and comfortable in general. The food is good. We did not appreciated at all the waiting time to get the room. Check in was at 3:00pm, but the room was not available and hsd to wait for so long after a long traveling day... That's a no,.. no. The breakfast took very long time with only a couple of tables occupied however it was good.

Reviewed on 23 Jun 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 featuring 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

Top hotels in Kenwood

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
The price is £132 per night from 1 Jul to 2 Jul
£132
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very Good! (4,265 reviews)
"Great location, we enjoyed our stay"

Reviewed on 23 Jun 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £160 per night from 1 Jul to 2 Jul
£160
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,918 reviews)
"Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual."

Reviewed on 24 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
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
The price is £117 per night from 6 Jul to 7 Jul
£117
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,334 reviews)
"The best value in Chicago.The staff is gracious and accommodating, the restaurant is an amazingly suprising, and a find at fair prices. Hidden away with easy access to the shoreline. At the doorstep of the Gold Coast without the hubbub."

Reviewed on 23 Jun 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,342 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.

Things to do

River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.