West Side Adventure Holidays
Book a Hotel + Flight or Car together to unlock savings
- 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,973, price is now €1,222 per person
€1,222
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Beautiful hotel centrally located
Reviewed on 16 Sept 2025
Park Hyatt Chicago
Downtown Chicago
Price was €2,266, price is now €1,437 per person
€1,437
per person
2 Nov - 7 Nov
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on 8 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,219, price is now €828 per person
€828
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on 9 Sept 2025
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,973, price is now €1,222 per person
€1,222
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Beautiful hotel centrally located
Reviewed on 16 Sept 2025
Park Hyatt Chicago
Downtown Chicago
Price was €2,266, price is now €1,437 per person
€1,437
per person
2 Nov - 7 Nov
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on 8 Sept 2025
The Langham, Chicago
Downtown Chicago
Price was €1,938, price is now €1,356 per person
€1,356
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
