Historic Route 66 Beach 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
€1,059
per person
24 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (3,012 reviews)
Can’t complain, everything was perfectly good!

Reviewed on 16 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,383
per person
24 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Love the the hotel, great location.

Reviewed on 17 Sept 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
€1,339
per person
24 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
€1,509
per person
24 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
The staff was super helpful and the room was clean and beautiful!

Reviewed on 16 Sept 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
€1,310
per person
24 Oct - 29 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
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.