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Chicago & Orlando

from Punta Cana

Best deal: £284

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.

Orlando

Orlando, a city in central Florida, is known for its iconic theme parks, vibrant nightlife, and world-class dining. Visit the famous Walt Disney World, explore the magical Universal Orlando Resort, or enjoy the vibrant arts scene in Downtown Orlando. Orlando's lush golf courses, shopping outlets, and the annual Epcot International Flower & Garden Festival make it a city full of fun and excitement.

Latest deals:

Chicago
&
Orlando
6 days
£284
7 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Thu 16/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
10 days
£284
3 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Mon 20/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
7 days
£284
6 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Fri 17/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
11 days
£284
3 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Mon 20/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
8 days
£284
6 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Fri 17/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
4 days
£284
3 days
Punta Cana - Chicago: Thu 16/10: £144
Go
Chicago - Orlando: Mon 20/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
12 days
£284
3 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Mon 20/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
7 days
£284
7 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Thu 16/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
8 days
£284
7 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Thu 16/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
9 days
£284
6 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Fri 17/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
10 days
£285
5 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Sat 18/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
2 days
£285
12 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Sat 11/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
3 days
£285
12 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Sat 11/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
5 days
£285
9 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Tue 14/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
8 days
£285
5 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Sat 18/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
6 days
£285
9 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Tue 14/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
9 days
£285
5 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Sat 18/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
2 days
£285
5 days
Punta Cana - Chicago: Thu 16/10: £144
Go
Chicago - Orlando: Sat 18/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
4 days
£285
9 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Tue 14/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
3 days
£290
4 days
Punta Cana - Chicago: Thu 16/10: £144
Go
Chicago - Orlando: Sun 19/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
11 days
£290
2 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Tue 21/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
9 days
£290
4 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Sun 19/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
4 days
£290
11 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Sun 12/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
5 days
£290
8 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Wed 15/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
5 days
£290
10 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Mon 13/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
2 days
£290
11 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Sun 12/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
12 days
£290
2 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Tue 21/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
10 days
£290
4 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Sun 19/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
7 days
£290
8 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Wed 15/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
6 days
£290
8 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Wed 15/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
4 days
£290
10 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Mon 13/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
3 days
£290
11 days
Punta Cana - Chicago: Thu 9/10: £144
Go
Chicago - Orlando: Sun 12/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
13 days
£290
2 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Tue 21/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
11 days
£290
4 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Sun 19/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
3 days
£290
10 days
Punta Cana - Chicago: Fri 10/10: £144
Go
Chicago - Orlando: Mon 13/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
5 days
£290
2 days
Punta Cana - Chicago: Thu 16/10: £144
Go
Chicago - Orlando: Tue 21/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
2 days
£327
13 days
Punta Cana - Chicago: Wed 8/10: £144
Go
Chicago - Orlando: Fri 10/10: £74
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
2 days
£357
3 days
Punta Cana - Chicago: Sat 18/10: £217
Go
Chicago - Orlando: Mon 20/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
3 days
£363
2 days
Punta Cana - Chicago: Sat 18/10: £217
Go
Chicago - Orlando: Tue 21/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
2 days
£374
6 days
Punta Cana - Chicago: Wed 15/10: £234
Go
Chicago - Orlando: Fri 17/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
5 days
£374
3 days
Punta Cana - Chicago: Wed 15/10: £234
Go
Chicago - Orlando: Mon 20/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
3 days
£375
5 days
Punta Cana - Chicago: Wed 15/10: £234
Go
Chicago - Orlando: Sat 18/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
4 days
£380
4 days
Punta Cana - Chicago: Wed 15/10: £234
Go
Chicago - Orlando: Sun 19/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
6 days
£380
2 days
Punta Cana - Chicago: Wed 15/10: £234
Go
Chicago - Orlando: Tue 21/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
8 days
£425
3 days
Punta Cana - Chicago: Sun 12/10: £285
Go
Chicago - Orlando: Mon 20/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
5 days
£425
6 days
Punta Cana - Chicago: Sun 12/10: £285
Go
Chicago - Orlando: Fri 17/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
4 days
£425
7 days
Punta Cana - Chicago: Sun 12/10: £285
Go
Chicago - Orlando: Thu 16/10: £31
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
6 days
£426
5 days
Punta Cana - Chicago: Sun 12/10: £285
Go
Chicago - Orlando: Sat 18/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
2 days
£426
9 days
Punta Cana - Chicago: Sun 12/10: £285
Go
Chicago - Orlando: Tue 14/10: £32
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄
Chicago
&
Orlando
7 days
£431
4 days
Punta Cana - Chicago: Sun 12/10: £285
Go
Chicago - Orlando: Sun 19/10: £37
Go
Orlando - Punta Cana: Thu 23/10: £109
Go
⌄

... 19 more possible dates exist ...