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Punta Cana & Boston

from Chicago

Best deal: £333

Punta Cana

Punta Cana, a town on the easternmost tip of the Dominican Republic, is known for its stunning beaches, clear waters, and vibrant nightlife. Visit the enchanting Hoyo Azul, a natural sinkhole filled with crystal-clear water, explore the bustling market at Plaza Bavaro, or relax on the idyllic Bavaro Beach. Punta Cana's luxury resorts, world-class golf courses, and the annual Carnival Punta Cana make it a Caribbean paradise.

Boston

Boston, one of the oldest cities in the U.S., is known for its rich history, prestigious universities, and diverse neighborhoods. Visit the historic Freedom Trail, explore the bustling Faneuil Hall Marketplace, or catch a game at Fenway Park. Boston's clam chowder, vibrant arts scene, and the annual Boston Marathon make it a city of tradition and innovation.

Latest deals:

Punta Cana
&
Boston
2 days
£333
2 days
Chicago - Punta Cana: Mon 29/12: £116
Go
Punta Cana - Boston: Wed 31/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
5 days
£368
7 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Fri 26/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
4 days
£368
8 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Thu 25/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
3 days
£368
9 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Wed 24/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
2 days
£368
10 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Tue 23/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
10 days
£368
2 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Wed 31/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
2 days
£368
9 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Wed 24/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
3 days
£368
8 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Thu 25/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
9 days
£368
2 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Wed 31/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
4 days
£368
7 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Fri 26/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
6 days
£378
6 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Sat 27/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
5 days
£378
6 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Sat 27/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
6 days
£378
5 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Sun 28/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
8 days
£378
4 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Mon 29/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
7 days
£378
4 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Mon 29/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
7 days
£378
5 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Sun 28/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
4 days
£388
2 days
Chicago - Punta Cana: Sat 27/12: £171
Go
Punta Cana - Boston: Wed 31/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
8 days
£391
3 days
Chicago - Punta Cana: Mon 22/12: £151
Go
Punta Cana - Boston: Tue 30/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
9 days
£391
3 days
Chicago - Punta Cana: Sun 21/12: £151
Go
Punta Cana - Boston: Tue 30/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
8 days
£392
7 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Fri 26/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
7 days
£392
8 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Thu 25/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
6 days
£392
9 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Wed 24/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
5 days
£392
10 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Tue 23/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
13 days
£392
2 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Wed 31/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
3 days
£393
2 days
Chicago - Punta Cana: Sun 28/12: £176
Go
Punta Cana - Boston: Wed 31/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
2 days
£398
4 days
Chicago - Punta Cana: Sat 27/12: £171
Go
Punta Cana - Boston: Mon 29/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
11 days
£402
4 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Mon 29/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
10 days
£402
5 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Sun 28/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
9 days
£402
6 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Sat 27/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
3 days
£411
3 days
Chicago - Punta Cana: Sat 27/12: £171
Go
Punta Cana - Boston: Tue 30/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
3 days
£415
12 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Sun 21/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
2 days
£415
13 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Sat 20/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
4 days
£415
11 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Mon 22/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
12 days
£415
3 days
Chicago - Punta Cana: Thu 18/12: £175
Go
Punta Cana - Boston: Tue 30/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
2 days
£416
3 days
Chicago - Punta Cana: Sun 28/12: £176
Go
Punta Cana - Boston: Tue 30/12: £173
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
7 days
£421
2 days
Chicago - Punta Cana: Wed 24/12: £204
Go
Punta Cana - Boston: Wed 31/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
2 days
£421
7 days
Chicago - Punta Cana: Wed 24/12: £204
Go
Punta Cana - Boston: Fri 26/12: £150
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
5 days
£431
4 days
Chicago - Punta Cana: Wed 24/12: £204
Go
Punta Cana - Boston: Mon 29/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
3 days
£431
6 days
Chicago - Punta Cana: Wed 24/12: £204
Go
Punta Cana - Boston: Sat 27/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄
Punta Cana
&
Boston
4 days
£431
5 days
Chicago - Punta Cana: Wed 24/12: £204
Go
Punta Cana - Boston: Sun 28/12: £160
Go
Boston - Chicago: Fri 2/01: £67
Go
⌄