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Chicago & Toronto

from Punta Cana

Best deal: £330

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
10 days
£330
3 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 18/05: £129
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
9 days
£330
4 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 17/05: £129
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
8 days
£330
5 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Fri 16/05: £129
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
7 days
£330
6 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
10 days
£337
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 18/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
9 days
£337
3 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 17/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
8 days
£337
4 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Fri 16/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
7 days
£337
5 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
9 days
£339
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 17/05: £129
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
8 days
£339
3 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Fri 16/05: £129
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
7 days
£339
4 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
11 days
£342
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Mon 19/05: £141
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
3 days
£354
10 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 11/05: £153
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
4 days
£354
9 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Mon 12/05: £153
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
5 days
£354
8 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Tue 13/05: £153
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
6 days
£354
7 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Wed 14/05: £153
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
4 days
£354
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Mon 12/05: £153
Go
Toronto - Punta Cana: Wed 14/05: £98
Go
⌄
Chicago
&
Toronto
3 days
£354
3 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 11/05: £153
Go
Toronto - Punta Cana: Wed 14/05: £98
Go
⌄
Chicago
&
Toronto
10 days
£355
5 days
Punta Cana - Chicago: Mon 5/05: £121
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
11 days
£355
4 days
Punta Cana - Chicago: Mon 5/05: £121
Go
Chicago - Toronto: Fri 16/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
12 days
£355
3 days
Punta Cana - Chicago: Mon 5/05: £121
Go
Chicago - Toronto: Sat 17/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
13 days
£355
2 days
Punta Cana - Chicago: Mon 5/05: £121
Go
Chicago - Toronto: Sun 18/05: £129
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
11 days
£357
3 days
Punta Cana - Chicago: Mon 5/05: £121
Go
Chicago - Toronto: Fri 16/05: £129
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
10 days
£357
4 days
Punta Cana - Chicago: Mon 5/05: £121
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
12 days
£357
2 days
Punta Cana - Chicago: Mon 5/05: £121
Go
Chicago - Toronto: Sat 17/05: £129
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
5 days
£361
7 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Tue 13/05: £153
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
4 days
£361
8 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Mon 12/05: £153
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
6 days
£361
6 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Wed 14/05: £153
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
3 days
£361
9 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 11/05: £153
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
5 days
£363
6 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Tue 13/05: £153
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
4 days
£363
7 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Mon 12/05: £153
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
3 days
£363
8 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 11/05: £153
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
6 days
£363
5 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Wed 14/05: £153
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
7 days
£373
8 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
8 days
£373
7 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Fri 16/05: £129
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
9 days
£373
6 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 17/05: £129
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
10 days
£373
5 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 18/05: £129
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
13 days
£373
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Wed 21/05: £129
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
12 days
£373
3 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Tue 20/05: £129
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
8 days
£375
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Fri 16/05: £129
Go
Toronto - Punta Cana: Sun 18/05: £143
Go
⌄
Chicago
&
Toronto
7 days
£375
3 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Sun 18/05: £143
Go
⌄
Chicago
&
Toronto
2 days
£378
4 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 10/05: £177
Go
Toronto - Punta Cana: Wed 14/05: £98
Go
⌄
Chicago
&
Toronto
2 days
£378
11 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 10/05: £177
Go
Toronto - Punta Cana: Wed 21/05: £98
Go
⌄
Chicago
&
Toronto
2 days
£385
10 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 10/05: £177
Go
Toronto - Punta Cana: Tue 20/05: £105
Go
⌄
Chicago
&
Toronto
11 days
£385
4 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Mon 19/05: £141
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
2 days
£387
9 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sat 10/05: £177
Go
Toronto - Punta Cana: Mon 19/05: £107
Go
⌄
Chicago
&
Toronto
7 days
£393
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Thu 15/05: £129
Go
Toronto - Punta Cana: Sat 17/05: £161
Go
⌄
Chicago
&
Toronto
3 days
£396
2 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 11/05: £153
Go
Toronto - Punta Cana: Tue 13/05: £140
Go
⌄
Chicago
&
Toronto
3 days
£397
12 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Sun 11/05: £153
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄
Chicago
&
Toronto
4 days
£397
11 days
Punta Cana - Chicago: Thu 8/05: £103
Go
Chicago - Toronto: Mon 12/05: £153
Go
Toronto - Punta Cana: Fri 23/05: £141
Go
⌄

... 11 more possible dates exist ...