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Toronto & Chicago

from Punta Cana

Best deal: £259

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.

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.

Latest deals:

Toronto
&
Chicago
4 days
£259
7 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 26/01: £84
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
5 days
£259
6 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Tue 27/01: £84
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
7 days
£259
4 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Thu 29/01: £84
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
4 days
£259
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 26/01: £84
Go
Chicago - Punta Cana: Wed 28/01: £90
Go
⌄
Toronto
&
Chicago
8 days
£259
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Fri 30/01: £84
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
3 days
£264
8 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
6 days
£264
5 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Wed 28/01: £89
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
3 days
£264
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Wed 28/01: £90
Go
⌄
Toronto
&
Chicago
2 days
£264
4 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Wed 28/01: £90
Go
⌄
Toronto
&
Chicago
2 days
£264
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Mon 26/01: £90
Go
⌄
Toronto
&
Chicago
9 days
£264
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 31/01: £89
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
2 days
£264
9 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Mon 2/02: £90
Go
⌄
Toronto
&
Chicago
5 days
£269
4 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Tue 27/01: £84
Go
Chicago - Punta Cana: Sat 31/01: £100
Go
⌄
Toronto
&
Chicago
4 days
£269
5 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 26/01: £84
Go
Chicago - Punta Cana: Sat 31/01: £100
Go
⌄
Toronto
&
Chicago
7 days
£269
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Thu 29/01: £84
Go
Chicago - Punta Cana: Sat 31/01: £100
Go
⌄
Toronto
&
Chicago
6 days
£274
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Wed 28/01: £89
Go
Chicago - Punta Cana: Sat 31/01: £100
Go
⌄
Toronto
&
Chicago
3 days
£274
6 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Sat 31/01: £100
Go
⌄
Toronto
&
Chicago
2 days
£274
7 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Sat 31/01: £100
Go
⌄
Toronto
&
Chicago
5 days
£297
7 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Tue 27/01: £84
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
4 days
£297
8 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 26/01: £84
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
7 days
£297
5 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Thu 29/01: £84
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
8 days
£297
4 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Fri 30/01: £84
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
10 days
£297
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 1/02: £84
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
3 days
£302
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Tue 27/01: £128
Go
⌄
Toronto
&
Chicago
2 days
£302
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Tue 27/01: £128
Go
⌄
Toronto
&
Chicago
2 days
£302
10 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
6 days
£302
6 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Wed 28/01: £89
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
3 days
£302
9 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
9 days
£302
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 31/01: £89
Go
Chicago - Punta Cana: Tue 3/02: £128
Go
⌄
Toronto
&
Chicago
4 days
£307
9 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 26/01: £84
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
5 days
£307
8 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Tue 27/01: £84
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
10 days
£307
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 1/02: £84
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
11 days
£307
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 2/02: £84
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
7 days
£307
6 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Thu 29/01: £84
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
8 days
£307
5 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Fri 30/01: £84
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
2 days
£312
11 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
3 days
£312
10 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
9 days
£312
4 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 31/01: £89
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
6 days
£312
7 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Wed 28/01: £89
Go
Chicago - Punta Cana: Wed 4/02: £138
Go
⌄
Toronto
&
Chicago
4 days
£320
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 26/01: £84
Go
Chicago - Punta Cana: Thu 29/01: £151
Go
⌄
Toronto
&
Chicago
4 days
£320
4 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Mon 26/01: £84
Go
Chicago - Punta Cana: Fri 30/01: £151
Go
⌄
Toronto
&
Chicago
5 days
£320
3 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Tue 27/01: £84
Go
Chicago - Punta Cana: Fri 30/01: £151
Go
⌄
Toronto
&
Chicago
5 days
£320
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Tue 27/01: £84
Go
Chicago - Punta Cana: Thu 29/01: £151
Go
⌄
Toronto
&
Chicago
3 days
£325
5 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Fri 30/01: £151
Go
⌄
Toronto
&
Chicago
2 days
£325
5 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Thu 29/01: £151
Go
⌄
Toronto
&
Chicago
3 days
£325
4 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sun 25/01: £89
Go
Chicago - Punta Cana: Thu 29/01: £151
Go
⌄
Toronto
&
Chicago
6 days
£325
2 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Wed 28/01: £89
Go
Chicago - Punta Cana: Fri 30/01: £151
Go
⌄
Toronto
&
Chicago
2 days
£325
6 days
Punta Cana - Toronto: Thu 22/01: £85
Go
Toronto - Chicago: Sat 24/01: £89
Go
Chicago - Punta Cana: Fri 30/01: £151
Go
⌄
Toronto
&
Chicago
4 days
£334
6 days
Punta Cana - Toronto: Fri 2/01: £160
Go
Toronto - Chicago: Tue 6/01: £84
Go
Chicago - Punta Cana: Mon 12/01: £90
Go
⌄
Toronto
&
Chicago
6 days
£334
4 days
Punta Cana - Toronto: Fri 2/01: £160
Go
Toronto - Chicago: Thu 8/01: £84
Go
Chicago - Punta Cana: Mon 12/01: £90
Go
⌄

... 65 more possible dates exist ...