Historic Route 66 All inclusive Holidays

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Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
€1,542
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,680
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on 1 Oct 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
€1,633
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
€1,704
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,913 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
€1,554
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (3,084 reviews)
The room was OK, but the bathroom needed some cleaning. Additionally, only one of the three elevators worked on the morning of our checkout. With the service staff using the one elevator and everyone checking out, it took almost 30 minutes to get from our room to the lobby.

Reviewed on 1 Oct 2026

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Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
€2,506
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
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Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
€1,542
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,680
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on 1 Oct 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
€1,633
per person
24 Nov - 28 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.