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Cancun & Chicago

from Boston

Best deal: £241

Cancun

Cancun, Mexico's premier tourist destination, enchants with its turquoise waters, pristine beaches, and vibrant nightlife. Experience the thrill of water sports, visit the nearby Mayan ruins at Tulum, or explore the Underwater Museum of Art. With its luxury resorts, vibrant coral reefs, and rich cultural events, Cancun is a tropical paradise.

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:

Cancun
&
Chicago
4 days
£241
11 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Thu 8/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
5 days
£241
10 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Fri 9/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
6 days
£241
9 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Sat 10/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
5 days
£241
9 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Sat 10/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
4 days
£241
10 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Fri 9/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
3 days
£241
11 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Thu 8/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
3 days
£254
12 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Wed 7/01: £100
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
6 days
£254
8 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Sun 11/01: £100
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
2 days
£254
12 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Wed 7/01: £100
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
7 days
£254
8 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Sun 11/01: £100
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
12 days
£258
3 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
11 days
£258
4 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
10 days
£258
5 days
Boston - Cancun: Sun 4/01: £102
Go
Cancun - Chicago: Wed 14/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
9 days
£258
5 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Wed 14/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
10 days
£258
4 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
11 days
£258
3 days
Boston - Cancun: Mon 5/01: £102
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
3 days
£259
10 days
Boston - Cancun: Tue 6/01: £120
Go
Cancun - Chicago: Fri 9/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
4 days
£259
9 days
Boston - Cancun: Tue 6/01: £120
Go
Cancun - Chicago: Sat 10/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
2 days
£259
11 days
Boston - Cancun: Tue 6/01: £120
Go
Cancun - Chicago: Thu 8/01: £87
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
2 days
£261
8 days
Boston - Cancun: Fri 9/01: £109
Go
Cancun - Chicago: Sun 11/01: £100
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
2 days
£265
4 days
Boston - Cancun: Tue 13/01: £109
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
4 days
£265
3 days
Boston - Cancun: Mon 12/01: £109
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
3 days
£265
4 days
Boston - Cancun: Mon 12/01: £109
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
2 days
£265
5 days
Boston - Cancun: Mon 12/01: £109
Go
Cancun - Chicago: Wed 14/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
5 days
£265
3 days
Boston - Cancun: Sun 11/01: £109
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
4 days
£265
4 days
Boston - Cancun: Sun 11/01: £109
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
3 days
£265
5 days
Boston - Cancun: Sun 11/01: £109
Go
Cancun - Chicago: Wed 14/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
6 days
£265
3 days
Boston - Cancun: Sat 10/01: £109
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
4 days
£265
5 days
Boston - Cancun: Sat 10/01: £109
Go
Cancun - Chicago: Wed 14/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
7 days
£265
3 days
Boston - Cancun: Fri 9/01: £109
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
6 days
£265
4 days
Boston - Cancun: Fri 9/01: £109
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
5 days
£265
5 days
Boston - Cancun: Fri 9/01: £109
Go
Cancun - Chicago: Wed 14/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
5 days
£265
4 days
Boston - Cancun: Sat 10/01: £109
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
3 days
£265
3 days
Boston - Cancun: Tue 13/01: £109
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
5 days
£272
8 days
Boston - Cancun: Tue 6/01: £120
Go
Cancun - Chicago: Sun 11/01: £100
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
10 days
£276
3 days
Boston - Cancun: Tue 6/01: £120
Go
Cancun - Chicago: Fri 16/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
9 days
£276
4 days
Boston - Cancun: Tue 6/01: £120
Go
Cancun - Chicago: Thu 15/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄
Cancun
&
Chicago
8 days
£276
5 days
Boston - Cancun: Tue 6/01: £120
Go
Cancun - Chicago: Wed 14/01: £104
Go
Chicago - Boston: Mon 19/01: £52
Go
⌄