Chicago holidays

Holiday deals on sale now, from city breaks and beach stays to tours. Choose a category to see the places and prices.

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3 on sale

USA Music Cities Fly Drive to New Orleans with Route 66 from Chicago

Chicago

12 Dec 2026 – 24 Dec 2026

£2,369

Sleepy San Fran, Sleepless in Seattle and Rockies Sleeper to Chicago - 12 Nights

San Francisco

6 Mar 2027 – 19 Mar 2027

£2,629

The Complete Route 66 Ultimate American Road Trip Experience (Tours Included)

Chicago

7 Dec 2027 – 24 Dec 2027

£2,699