West Side All inclusive Holidays
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- Better togetherSave up to €185 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,522, price is now €1,023 per person
€1,023
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on 1 Dec 2025
Pendry Chicago
Downtown Chicago
Price was €955, price is now €717 per person
€717
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Inviting lobby area with comfortable bar on the side. Excellent cocktails!
19th floor room with roomy bathroom & excellent water pressure. Soft, comfortable sheets on moderately firm mattresses. Very prompt room service with nice choices 24/7 (we ordered at midnight). Located about 2 blocks from Miracle Mile. On top of that, customer service was outstanding!
Reviewed on 1 Dec 2025
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was €925, price is now €723 per person
€723
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Clean room and kind staff. First hotel I’ve been to that actually had a key to open the door, very cool. Would stay again.
Reviewed on 30 Nov 2025
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,522, price is now €1,023 per person
€1,023
per person
1 Feb - 6 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on 1 Dec 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
