Chicago holidays
Travel month
3 on sale
USA Music Cities Fly Drive to New Orleans with Route 66 from Chicago
Chicago
21 Nov 2026 – 3 Dec 2026
£2,419
Sleepy San Fran, Sleepless in Seattle and Rockies Sleeper to Chicago - 12 Nights
San Francisco
6 Mar 2027 – 19 Mar 2027
£2,619
The Complete Route 66 Ultimate American Road Trip Experience (Tours Included)
Chicago
23 Nov 2026 – 10 Dec 2026
£2,869