Kenwood Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 when you book a flight and hotel together*

  • Find the right fit

    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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was €916, price is now €774 per person
€774
per person
30 Apr - 3 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Food was great at the Aviator. The room was clean, quiet and comfortable and everyone went out of their way at the front desk to accommodate us.

Reviewed on 26 Feb 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,136, price is now €890 per person
€890
per person
30 Apr - 3 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on 22 Feb 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,032, price is now €848 per person
€848
per person
30 Apr - 3 May
found 19 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
Having my valet service was very helpful for me and my family kinda pricey but worth it

Reviewed on 24 Feb 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 which includes 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

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 €268 per night from 13 Mar to 14 Mar
€268
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,937 reviews)
Shortly after our check in when noticed our room did not have heat called the operator only to be told the hotels boiler was out, had to call a 2nd time because the toilet wouldn't flush finally when the maintenance guy came to fix the toilet he said he could get us a space heater we was so excited ...

Reviewed on 26 Feb 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 €139 per night from 2 Mar to 3 Mar
€139
2 Mar - 3 Mar
includes taxes & fees
9.4/10 Exceptional! (3,415 reviews)
To recessed lights in the ceiling near the windows the windows would not shut off. We tried every little light switch in the room eight ways to Sunday and could not get those recessed lights off. The only way to shut them off was to take the card out to stop the electricity in the room. But then ...

Reviewed on 26 Feb 2026

Hotel Riu Plaza Chicago
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
Fully refundableReserve now, pay when you stay
The price is €102 per night from 4 Mar to 5 Mar
€102
4 Mar - 5 Mar
includes taxes & fees
8.6/10 Excellent! (5,685 reviews)
Service was great, and the staff was very kind.

Reviewed on 26 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,663 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 €774. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.