Kenwood Holidays

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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.
  • Pool
    Aug 3 - Aug 8

    Hilton Garden Inn Chicago Downtown South Loop + Flight

    Downtown Chicago
    5 nights
    3.0 star property
    8.8/10 - Excellent (2,014 reviews)
    "."
    Reviewed May 28, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,740
    £2,294
    per traveller
    found 8 hours ago
    Hilton Garden Inn Chicago Downtown South Loop
  • Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels
    Aug 3 - Aug 8

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,398 reviews)
    "Shea was wondering! A couple of hiccups but she handled with ease. I would definitely stay again because of the service I received."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,801
    £2,308
    per traveller
    found 8 hours ago
    Sports Illustrated Resorts Chicago
  • 2 bars/lounges, rooftop bar
    Aug 3 - Aug 8

    theWit Chicago, a Hilton Hotel + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Great location. Staff was professional and helpful. Restaurant State and Lake had great breakfast and ambience. Roof at theWit was amazing with a good happy hour, great ambience and vibe with city views."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £4,011
    £2,455
    per traveller
    found 8 hours ago
    theWit Chicago, a Hilton Hotel
  • Meeting facility
    Aug 3 - Aug 8

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (1,371 reviews)
    "Great stay, very clean and comfortable."
    Reviewed May 27, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,920
    £2,403
    per traveller
    found 8 hours ago
    Thompson Chicago, by Hyatt
  • Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
    Aug 3 - Aug 8

    Holiday Inn & Suites Chicago - Downtown by IHG + Flight

    Downtown Chicago
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,006 reviews)
    "Convenient parking and staff were helpful in suggesting restaurants and shopping close by"
    Reviewed May 28, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £3,905
    £2,404
    per traveller
    found 8 hours ago
    Holiday Inn & Suites Chicago - Downtown by IHG

Where to stay in Kenwood

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

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

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 £178 per night from 2 Jun to 3 Jun
£178
2 Jun - 3 Jun
includes taxes & fees
8/10 Very Good! (10,119 reviews)
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."

Reviewed on 27 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £224 per night from 28 Jun to 29 Jun
£224
28 Jun - 29 Jun
includes taxes & fees
9.4/10 Exceptional! (4,275 reviews)
"Terrific location blessed with a wonderful staff. Especially grand breakfast too"

Reviewed on 28 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £135 per night from 28 Jun to 29 Jun
£135
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,485 reviews)
"we ended up having to pay $90 on top of what we paid on this app for no reason, our hotel was fully paid yet they charged us this without explaining what it was for, I didn’t want to ask because I was already stressed about not being able to check in early and being late to our activities for the ..."

Reviewed on 28 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,550 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.