Historic Route 66 Beach Holidays

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Top flight + Beach hotel deals in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
NZ$1,333
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
NZ$1,540
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Love the the hotel, great location.

Reviewed on 17 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
NZ$1,365
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) 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

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
NZ$1,408
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Clean room, nice location

Reviewed on 15 Sept 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
NZ$1,472
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (2,381 reviews)
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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.