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Chicago & Toronto

from St Louis

Best deal: £293

Chicago

Chicago, Illinois, nestled along Lake Michigan, is famed for its bold architecture, deep-dish pizza, and jazz music. Take an architectural river cruise, visit the expansive Art Institute of Chicago, or enjoy the view from the Willis Tower Skydeck. Chicago's bustling Magnificent Mile, numerous parks, and annual events like the Chicago Air and Water Show make it a city of architectural marvels and cultural depth.

Toronto

Toronto, the capital of Ontario, is a dynamic metropolis with a core of soaring skyscrapers, all dwarfed by the iconic CN Tower. Visit the historic Casa Loma, explore the bustling St. Lawrence Market, or stroll through the vast High Park. Toronto's diverse food scene, vibrant arts community, and the annual Toronto International Film Festival make it a city of multicultural charm and creativity.

Latest deals:

Chicago
&
Toronto
13 days
£293
2 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Thu 27/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
3 days
£293
2 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Mon 17/03: £82
Toronto - St Louis: Wed 19/03: £171
Go
⌄
Chicago
&
Toronto
3 days
£293
3 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Mon 17/03: £82
Toronto - St Louis: Thu 20/03: £171
Go
⌄
Chicago
&
Toronto
4 days
£293
2 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Tue 18/03: £82
Toronto - St Louis: Thu 20/03: £171
Go
⌄
Chicago
&
Toronto
3 days
£293
8 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Mon 17/03: £82
Toronto - St Louis: Tue 25/03: £171
Go
⌄
Chicago
&
Toronto
4 days
£293
7 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Tue 18/03: £82
Toronto - St Louis: Tue 25/03: £171
Go
⌄
Chicago
&
Toronto
5 days
£293
6 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Wed 19/03: £82
Toronto - St Louis: Tue 25/03: £171
Go
⌄
Chicago
&
Toronto
8 days
£293
3 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Sat 22/03: £82
Toronto - St Louis: Tue 25/03: £171
Go
⌄
Chicago
&
Toronto
9 days
£293
2 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Sun 23/03: £82
Toronto - St Louis: Tue 25/03: £171
Go
⌄
Chicago
&
Toronto
3 days
£293
9 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Mon 17/03: £82
Toronto - St Louis: Wed 26/03: £171
Go
⌄
Chicago
&
Toronto
4 days
£293
8 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Tue 18/03: £82
Toronto - St Louis: Wed 26/03: £171
Go
⌄
Chicago
&
Toronto
12 days
£293
3 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Wed 26/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
8 days
£293
4 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Sat 22/03: £82
Toronto - St Louis: Wed 26/03: £171
Go
⌄
Chicago
&
Toronto
9 days
£293
3 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Sun 23/03: £82
Toronto - St Louis: Wed 26/03: £171
Go
⌄
Chicago
&
Toronto
10 days
£293
2 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Mon 24/03: £82
Toronto - St Louis: Wed 26/03: £171
Go
⌄
Chicago
&
Toronto
3 days
£293
12 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Mon 17/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
4 days
£293
11 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Tue 18/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
5 days
£293
10 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Wed 19/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
8 days
£293
7 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Sat 22/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
9 days
£293
6 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Sun 23/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
10 days
£293
5 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Mon 24/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
11 days
£293
4 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Tue 25/03: £82
Toronto - St Louis: Sat 29/03: £171
Go
⌄
Chicago
&
Toronto
5 days
£293
7 days
St Louis - Chicago: Fri 14/03: £40
Chicago - Toronto: Wed 19/03: £82
Toronto - St Louis: Wed 26/03: £171
Go
⌄
Chicago
&
Toronto
10 days
£309
4 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sun 9/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
9 days
£309
5 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sat 8/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
8 days
£309
6 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Fri 7/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
7 days
£309
7 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Thu 6/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
2 days
£309
12 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sat 1/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
5 days
£309
9 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Tue 4/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
4 days
£309
10 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Mon 3/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
3 days
£309
11 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sun 2/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
11 days
£309
3 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Mon 10/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
6 days
£309
8 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Wed 5/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
12 days
£309
2 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Tue 11/03: £82
Toronto - St Louis: Thu 13/03: £171
Go
⌄
Chicago
&
Toronto
6 days
£309
9 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Wed 5/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
3 days
£309
12 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sun 2/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
4 days
£309
11 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Mon 3/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
5 days
£309
10 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Tue 4/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
7 days
£309
8 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Thu 6/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
8 days
£309
7 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Fri 7/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
9 days
£309
6 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sat 8/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
10 days
£309
5 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sun 9/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
11 days
£309
4 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Mon 10/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
11 days
£309
2 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Mon 10/03: £82
Toronto - St Louis: Wed 12/03: £171
Go
⌄
Chicago
&
Toronto
13 days
£309
2 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Wed 12/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
2 days
£309
13 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sat 1/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
12 days
£309
3 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Tue 11/03: £82
Toronto - St Louis: Fri 14/03: £171
Go
⌄
Chicago
&
Toronto
2 days
£309
2 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Sat 1/03: £82
Toronto - St Louis: Mon 3/03: £171
Go
⌄
Chicago
&
Toronto
8 days
£309
5 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Fri 7/03: £82
Toronto - St Louis: Wed 12/03: £171
Go
⌄
Chicago
&
Toronto
6 days
£309
3 days
St Louis - Chicago: Thu 27/02: £56
Chicago - Toronto: Wed 5/03: £82
Toronto - St Louis: Sat 8/03: £171
Go
⌄

... 44 more possible dates exist ...