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Chicago & Toronto

from Punta Cana

Best deal: £255

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
9 days
£255
2 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 17/05: £52
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
8 days
£255
3 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Fri 16/05: £52
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
7 days
£255
4 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Thu 15/05: £52
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
9 days
£272
4 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 17/05: £52
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
8 days
£272
5 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Fri 16/05: £52
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
7 days
£272
6 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Thu 15/05: £52
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
10 days
£272
3 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sun 18/05: £52
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
5 days
£276
6 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Tue 13/05: £73
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
4 days
£276
7 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Mon 12/05: £73
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
6 days
£276
5 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Wed 14/05: £73
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
2 days
£276
9 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 10/05: £73
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
3 days
£276
8 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sun 11/05: £73
Go
Toronto - Punta Cana: Mon 19/05: £106
Go
⌄
Chicago
&
Toronto
6 days
£277
3 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Thu 8/05: £73
Go
Toronto - Punta Cana: Sun 11/05: £107
Go
⌄
Chicago
&
Toronto
7 days
£277
2 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Fri 9/05: £73
Go
Toronto - Punta Cana: Sun 11/05: £107
Go
⌄
Chicago
&
Toronto
10 days
£279
2 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sun 18/05: £52
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
9 days
£279
3 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 17/05: £52
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
8 days
£279
4 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Fri 16/05: £52
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
7 days
£279
5 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Thu 15/05: £52
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
6 days
£285
2 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Thu 8/05: £73
Go
Toronto - Punta Cana: Sat 10/05: £115
Go
⌄
Chicago
&
Toronto
7 days
£286
2 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Thu 15/05: £52
Go
Toronto - Punta Cana: Sat 17/05: £137
Go
⌄
Chicago
&
Toronto
13 days
£286
2 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Thu 15/05: £52
Go
Toronto - Punta Cana: Sat 17/05: £137
Go
⌄
Chicago
&
Toronto
9 days
£291
6 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 17/05: £52
Go
Toronto - Punta Cana: Fri 23/05: £142
Go
⌄
Chicago
&
Toronto
7 days
£291
8 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Thu 15/05: £52
Go
Toronto - Punta Cana: Fri 23/05: £142
Go
⌄
Chicago
&
Toronto
8 days
£291
7 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Fri 16/05: £52
Go
Toronto - Punta Cana: Fri 23/05: £142
Go
⌄
Chicago
&
Toronto
12 days
£291
3 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Tue 20/05: £52
Go
Toronto - Punta Cana: Fri 23/05: £142
Go
⌄
Chicago
&
Toronto
10 days
£291
5 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sun 18/05: £52
Go
Toronto - Punta Cana: Fri 23/05: £142
Go
⌄
Chicago
&
Toronto
13 days
£291
2 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Wed 21/05: £52
Go
Toronto - Punta Cana: Fri 23/05: £142
Go
⌄
Chicago
&
Toronto
8 days
£292
2 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Fri 16/05: £52
Go
Toronto - Punta Cana: Sun 18/05: £143
Go
⌄
Chicago
&
Toronto
7 days
£292
3 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Thu 15/05: £52
Go
Toronto - Punta Cana: Sun 18/05: £143
Go
⌄
Chicago
&
Toronto
3 days
£293
10 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sun 11/05: £73
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
6 days
£293
7 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Wed 14/05: £73
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
5 days
£293
8 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Tue 13/05: £73
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
4 days
£293
9 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Mon 12/05: £73
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
2 days
£293
11 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 10/05: £73
Go
Toronto - Punta Cana: Wed 21/05: £123
Go
⌄
Chicago
&
Toronto
6 days
£300
5 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Thu 8/05: £73
Go
Toronto - Punta Cana: Tue 13/05: £130
Go
⌄
Chicago
&
Toronto
2 days
£300
10 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 10/05: £73
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
3 days
£300
9 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sun 11/05: £73
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
4 days
£300
8 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Mon 12/05: £73
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
5 days
£300
7 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Tue 13/05: £73
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
6 days
£300
6 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Wed 14/05: £73
Go
Toronto - Punta Cana: Tue 20/05: £130
Go
⌄
Chicago
&
Toronto
7 days
£300
4 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Fri 9/05: £73
Go
Toronto - Punta Cana: Tue 13/05: £130
Go
⌄
Chicago
&
Toronto
8 days
£300
3 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Sat 10/05: £73
Go
Toronto - Punta Cana: Tue 13/05: £130
Go
⌄
Chicago
&
Toronto
3 days
£300
2 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sun 11/05: £73
Go
Toronto - Punta Cana: Tue 13/05: £130
Go
⌄
Chicago
&
Toronto
2 days
£300
3 days
Punta Cana - Chicago: Thu 8/05: £97
Go
Chicago - Toronto: Sat 10/05: £73
Go
Toronto - Punta Cana: Tue 13/05: £130
Go
⌄
Chicago
&
Toronto
9 days
£300
2 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Sun 11/05: £73
Go
Toronto - Punta Cana: Tue 13/05: £130
Go
⌄
Chicago
&
Toronto
3 days
£305
6 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Mon 5/05: £101
Go
Toronto - Punta Cana: Sun 11/05: £107
Go
⌄
Chicago
&
Toronto
2 days
£305
7 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Sun 4/05: £101
Go
Toronto - Punta Cana: Sun 11/05: £107
Go
⌄
Chicago
&
Toronto
4 days
£305
5 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Tue 6/05: £101
Go
Toronto - Punta Cana: Sun 11/05: £107
Go
⌄
Chicago
&
Toronto
5 days
£305
4 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Wed 7/05: £101
Go
Toronto - Punta Cana: Sun 11/05: £107
Go
⌄
Chicago
&
Toronto
9 days
£307
6 days
Punta Cana - Chicago: Fri 2/05: £97
Go
Chicago - Toronto: Sun 11/05: £73
Go
Toronto - Punta Cana: Sat 17/05: £137
Go
⌄

... 68 more possible dates exist ...