
Hillside Holidays
Photo by Joe Farmer
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Top Flight + Hotel Deals in Hillside
Price found within the past 48 hours. Click for updated prices.

The Emily Hotel
Downtown Chicago
Price was €1,228, price is now €755 per person
€755
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,927, price is now €1,159 per person
€1,159
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 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.
Reviewed on 22 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 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on 21 Aug 2025
Top hotels in Hillside

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €151 per night from 1 Sept to 2 Sept
€151
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

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €104 per night from 24 Aug to 25 Aug
€104
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (8,982 reviews)
"Experience what it must have felt like to attend the 1893 Worlds Fair"
Reviewed on 22 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 €152 per night from 3 Sept to 4 Sept
€152
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,743 reviews)
"Great breakfast, good location."
Reviewed on 22 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.
Popular places to visit

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Hillside

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
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.