Chicago & Philadelphia

Both destinations in one trip from Cancun

Chicago

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.

Philadelphia

Philadelphia

Philadelphia, Pennsylvania, the birthplace of America, is steeped in history and cultural richness. Visit the Liberty Bell, explore the Philadelphia Museum of Art, or stroll through the historic streets of Old City. Philadelphia's diverse culinary scene, including its famous cheesesteaks, and annual events like the Philadelphia Flower Show, make it a city of brotherly love and cultural depth.

Latest deals

4 + 8 days £520 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 8/05 · £115 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
4 + 9 days £520 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 8/05 · £115 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
8 + 4 days £520 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Wed 12/05 · £115 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
7 + 5 days £520 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Tue 11/05 · £115 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
8 + 5 days £520 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Wed 12/05 · £115 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
11 + 2 days £520 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 15/05 · £115 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
4 + 10 days £520 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 8/05 · £115 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
7 + 7 days £520 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Tue 11/05 · £115 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
8 + 6 days £520 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Wed 12/05 · £115 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
11 + 3 days £520 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 15/05 · £115 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
4 + 3 days £520 Tue 4 May – Tue 11 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 8/05 · £115 Go
Philadelphia → Cancun · Tue 11/05 · £205 Go
4 + 2 days £520 Tue 4 May – Mon 10 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 8/05 · £115 Go
Philadelphia → Cancun · Mon 10/05 · £205 Go
7 + 6 days £520 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Tue 11/05 · £115 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
8 + 7 days £524 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Wed 12/05 · £115 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go
11 + 4 days £524 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 15/05 · £115 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go
7 + 8 days £524 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Tue 11/05 · £115 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go
4 + 4 days £524 Tue 4 May – Wed 12 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 8/05 · £115 Go
Philadelphia → Cancun · Wed 12/05 · £209 Go
4 + 11 days £524 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sat 8/05 · £115 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go
2 + 12 days £548 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 6/05 · £143 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
10 + 3 days £548 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 14/05 · £143 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
9 + 4 days £548 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 13/05 · £143 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
2 + 10 days £548 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 6/05 · £143 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
3 + 9 days £548 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 7/05 · £143 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
2 + 5 days £548 Tue 4 May – Tue 11 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 6/05 · £143 Go
Philadelphia → Cancun · Tue 11/05 · £205 Go
3 + 3 days £548 Tue 4 May – Mon 10 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 7/05 · £143 Go
Philadelphia → Cancun · Mon 10/05 · £205 Go
9 + 3 days £548 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 13/05 · £143 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
10 + 2 days £548 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 14/05 · £143 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
2 + 11 days £548 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 6/05 · £143 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
3 + 10 days £548 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 7/05 · £143 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
5 + 8 days £548 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sun 9/05 · £143 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
5 + 7 days £548 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sun 9/05 · £143 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
6 + 6 days £548 Tue 4 May – Sun 16 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Mon 10/05 · £143 Go
Philadelphia → Cancun · Sun 16/05 · £205 Go
3 + 11 days £548 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 7/05 · £143 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
6 + 8 days £548 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Mon 10/05 · £143 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
3 + 4 days £548 Tue 4 May – Tue 11 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 7/05 · £143 Go
Philadelphia → Cancun · Tue 11/05 · £205 Go
2 + 4 days £548 Tue 4 May – Mon 10 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 6/05 · £143 Go
Philadelphia → Cancun · Mon 10/05 · £205 Go
5 + 2 days £548 Tue 4 May – Tue 11 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sun 9/05 · £143 Go
Philadelphia → Cancun · Tue 11/05 · £205 Go
5 + 9 days £548 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sun 9/05 · £143 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
12 + 2 days £548 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sun 16/05 · £143 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
10 + 4 days £548 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 14/05 · £143 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
3 + 2 days £548 Tue 4 May – Sun 9 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 7/05 · £143 Go
Philadelphia → Cancun · Sun 9/05 · £205 Go
6 + 7 days £548 Tue 4 May – Mon 17 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Mon 10/05 · £143 Go
Philadelphia → Cancun · Mon 17/05 · £205 Go
9 + 5 days £548 Tue 4 May – Tue 18 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 13/05 · £143 Go
Philadelphia → Cancun · Tue 18/05 · £205 Go
2 + 3 days £548 Tue 4 May – Sun 9 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 6/05 · £143 Go
Philadelphia → Cancun · Sun 9/05 · £205 Go
10 + 5 days £551 Tue 17 Nov – Wed 2 Dec
Cancun → Chicago · Tue 17/11 · £223 Go
Chicago → Philadelphia · Fri 27/11 · £63 Go
Philadelphia → Cancun · Wed 2/12 · £265 Go
8 + 7 days £551 Tue 17 Nov – Wed 2 Dec
Cancun → Chicago · Tue 17/11 · £223 Go
Chicago → Philadelphia · Wed 25/11 · £63 Go
Philadelphia → Cancun · Wed 2/12 · £265 Go
2 + 13 days £552 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Thu 6/05 · £143 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go
10 + 5 days £552 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 14/05 · £143 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go
3 + 12 days £552 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Fri 7/05 · £143 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go
5 + 10 days £552 Tue 4 May – Wed 19 May
Cancun → Chicago · Tue 4/05 · £200 Go
Chicago → Philadelphia · Sun 9/05 · £143 Go
Philadelphia → Cancun · Wed 19/05 · £209 Go

... 29 more possible dates exist ...