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Chicago & Cancun

from Philadelphia

Best deal: £213

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.

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.

Latest deals:

Chicago
&
Cancun
4 days
£213
8 days
Philadelphia - Chicago: Sat 14/03: £66
Go
Chicago - Cancun: Wed 18/03: £68
Go
Cancun - Philadelphia: Thu 26/03: £79
Go
⌄
Chicago
&
Cancun
4 days
£213
9 days
Philadelphia - Chicago: Sat 14/03: £66
Go
Chicago - Cancun: Wed 18/03: £68
Go
Cancun - Philadelphia: Fri 27/03: £79
Go
⌄
Chicago
&
Cancun
4 days
£222
3 days
Philadelphia - Chicago: Sat 14/03: £66
Go
Chicago - Cancun: Wed 18/03: £68
Go
Cancun - Philadelphia: Sat 21/03: £88
Go
⌄
Chicago
&
Cancun
4 days
£222
10 days
Philadelphia - Chicago: Sat 14/03: £66
Go
Chicago - Cancun: Wed 18/03: £68
Go
Cancun - Philadelphia: Sat 28/03: £88
Go
⌄
Chicago
&
Cancun
11 days
£227
4 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Sat 11/04: £68
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
11 days
£227
3 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Sat 11/04: £68
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
7 days
£260
7 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Tue 7/04: £101
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
5 days
£260
10 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Sun 5/04: £101
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
6 days
£260
9 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Mon 6/04: £101
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
7 days
£260
8 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Tue 7/04: £101
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
5 days
£260
9 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Sun 5/04: £101
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
6 days
£260
8 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Mon 6/04: £101
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
13 days
£260
2 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Mon 13/04: £101
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
8 days
£262
6 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Wed 8/04: £103
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
9 days
£262
5 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Thu 9/04: £103
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
10 days
£262
4 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Fri 10/04: £103
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
12 days
£262
3 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Sun 12/04: £103
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
12 days
£262
2 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Sun 12/04: £103
Go
Cancun - Philadelphia: Tue 14/04: £79
Go
⌄
Chicago
&
Cancun
8 days
£262
7 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Wed 8/04: £103
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
9 days
£262
6 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Thu 9/04: £103
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄
Chicago
&
Cancun
10 days
£262
5 days
Philadelphia - Chicago: Tue 31/03: £80
Go
Chicago - Cancun: Fri 10/04: £103
Go
Cancun - Philadelphia: Wed 15/04: £79
Go
⌄