Kenwood Holidays

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  • Better together

    Save up to €900 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Couples treatment room(s), sauna, body treatments, aromatherapy
    Jul 9 - Jul 13

    Wind Creek Southland Casino and Hotel + Flight

    East Hazel Crest
    4 nights
    4.0 star property
    9.4/10 - Exceptional (420 reviews)
    "Overall, this hotel is very nice! The bed was comfortable with clean sheets. The shower was amazing, they have Starbucks downstairs and a steakhouse on the 17th floor! The only downside was the pool seemed very foggy and the hot tub was NOT clean! There was some buildup of dirt in the hot tub. Also, the lights in our room were acting weird at some points which was kind of spooky."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,146
    €946
    per traveller
    found 1 day ago
    Wind Creek Southland Casino and Hotel
  • Smart TV
    Jul 16 - Jul 20

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,600
    €1,196
    per traveller
    found 19 hours ago
    Level Chicago Fulton Market
  • Dinner served
    Jul 16 - Jul 20

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,005 reviews)
    "Nice staff clean room would stay again."
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,573
    €1,265
    per traveller
    found 19 hours ago
    Kimpton Gray Hotel by IHG
  • Indoor wedding
    Jul 9 - Jul 13

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,374 reviews)
    "Great hotel and close to everything we wanted to do in the area,got 2 great places to eat in the lobby and a Dunkin’ Donuts close by..if your new and looking for that DD basically go all the way down in the lobby,we were trying to find it for the longest lol but other than that would definitely recommend this hotel"
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,397
    €1,160
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Room service – dining
    Jul 9 - Jul 13

    The Wade + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    8.4/10 - Very good (1,852 reviews)
    "It was good. Had a bad experience with the bar. Drinks overpriced and then my credit card was charged for another party’s entire order."
    Reviewed May 30, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,526
    €1,293
    per traveller
    found 1 day ago
    The Wade

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 €140 per night from 30 Jun to 1 Jul
€140
30 Jun - 1 Jul
includes taxes & fees
8/10 Very Good! (10,221 reviews)
"Fantastic room and location."

Reviewed on 9 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is €125 per night from 28 Jun to 29 Jun
€125
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,545 reviews)
"Our room was spacious and very clean"

Reviewed on 8 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €170 per night from 29 Jun to 30 Jun
€170
29 Jun - 30 Jun
includes taxes & fees
8.2/10 Very Good! (1,569 reviews)
"Honestly during my trip I stayed at 6 Chicago hotels and this one was my favorite along with the Midlan hotel. Both exquisite, don’t forget to check out the roof top! I almost left without seeing the view it gorgeous!"

Reviewed on 8 Jun 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,524 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

How much does a Kenwood holiday package cost?
Get set to book, because a trip to Kenwood starts from only . When you bundle your hotels, flights and car rentals into a package, you'll score the biggest bargains.
How do I get a cheap travel package to Kenwood?
Browse and book everything all in one place with our Kenwood holiday packages. We have incredible bargains on hotels, flights, tours and more that'll keep your travel budget happy and adventurous side satisfied. And, with more than 550 air carriers and 1,000,000 properties globally to pick from, you'll have the flexibility to mix and match.
Where should I stay in Kenwood?
Urban adventurers come from far and wide to see University of Chicago and Chicago Museum of Science and Industry in Kenwood. Book yourself a room within walking distance of these popular attractions and visit them at your leisure.
What are the top hotels in Kenwood?
Get your escape off to a fantastic start by staying at Best Western Plus Hyde Park Chicago Hotel. It's one of most popular properties in Kenwood. Another leading option is Chicago Lake Shore Hotel.
How far in advance should I book my Kenwood holiday?
It's difficult to pick the perfect time for airfares, but we usually say the earlier, the better. Most international journeys on Expedia become available up to a year in advance. If you're booking late, don't stress. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Kenwood travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to build your ideal Kenwood package. Once you've made your booking, you can add on all the fun stuff like tours and activities. Remember — the more you bundle, the more discounts you'll get!
What should I know before booking a Kenwood travel package?
You'll save plenty with an Expedia travel package. Bundle your flights, rental cars and hotels and enjoy exciting discounts. Hotels aren't your only option, though. Book with us and choose from beachfront villas, creek-side mountain cabins and even glamping tents!
Can I choose my airline with a Kenwood Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply choose the carrier you want and craft your ideal Kenwood getaway.
If I'm not able to travel, can I cancel my Kenwood holiday package?
Don't worry if you're rethinking your Kenwood holiday package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We totally get that your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Popular places to visit

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 fascinating museums and acclaimed theatre scene in this vibrant area.

KAM Synagogue

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
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.