
Kenwood Holidays
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Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was €1,276, price is now €844 per person
€844
per person
4 Oct - 10 Oct
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,621 reviews)
Check in was easy and it felt very safe. Room was clean and was good sized for a Chicago hotel.
Reviewed on 21 Aug 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,927, price is now €1,160 per person
€1,160
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug 2025

The Royal Sonesta Chicago River North
Downtown Chicago
Price was €1,428, price is now €866 per person
€866
per person
4 Oct - 10 Oct
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone there was friendly and gave us a lot of places to go eat for our one year anniversary
Reviewed on 21 Aug 2025


Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €1,712, price is now €1,116 per person
€1,116
per person
4 Oct - 10 Oct
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on 17 Aug 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
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.
Top hotels in Kenwood

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €190 per night from 14 Sept to 15 Sept
€190
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,006 reviews)
"Great history . Staff was excellent"
Reviewed on 19 Aug 2025

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €152 per night from 1 Sept to 2 Sept
€152
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"
Reviewed on 19 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €154 per night from 4 Sept to 5 Sept
€154
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (4,729 reviews)
"The hotel was wonderfully nestled downtown and an easy walk to sites and restaurants."
Reviewed on 18 Aug 2025
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
Popular places to visit
KAM Synagogue
Find out about the history of Chicago when you spend time at KAM Synagogue. Amble around this vibrant area's lakeside or experience its fascinating museums.
Things to do

Chicago By Night River & Lake Cruise
€39
per adult
96% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
€35
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.