Historic Route 66 Pet-friendly Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
€1,460
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on 12 Oct 2026

Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all trips
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
€849
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
€1,460
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on 12 Oct 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,079
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Súper cerca a todas las atracciones de Chicago

Reviewed on 12 Oct 2026

Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all trips
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.