Punta Cana & Boston

Both destinations in one trip from Chicago

£396 Best deal

Punta Cana

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

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

3 + 8 days £396 Mon 16 Nov – Fri 27 Nov

Chicago → Punta Cana · Mon 16/11 · £143 Go

Punta Cana → Boston · Thu 19/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

5 + 6 days £396 Mon 16 Nov – Fri 27 Nov

Chicago → Punta Cana · Mon 16/11 · £143 Go

Punta Cana → Boston · Sat 21/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

6 + 5 days £396 Mon 16 Nov – Fri 27 Nov

Chicago → Punta Cana · Mon 16/11 · £143 Go

Punta Cana → Boston · Sun 22/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

7 + 4 days £396 Mon 16 Nov – Fri 27 Nov

Chicago → Punta Cana · Mon 16/11 · £143 Go

Punta Cana → Boston · Mon 23/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

8 + 3 days £396 Mon 16 Nov – Fri 27 Nov

Chicago → Punta Cana · Mon 16/11 · £143 Go

Punta Cana → Boston · Tue 24/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

9 + 2 days £396 Mon 16 Nov – Fri 27 Nov

Chicago → Punta Cana · Mon 16/11 · £143 Go

Punta Cana → Boston · Wed 25/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

6 + 8 days £403 Fri 13 Nov – Fri 27 Nov

Chicago → Punta Cana · Fri 13/11 · £150 Go

Punta Cana → Boston · Thu 19/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

11 + 3 days £403 Fri 13 Nov – Fri 27 Nov

Chicago → Punta Cana · Fri 13/11 · £150 Go

Punta Cana → Boston · Tue 24/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

10 + 4 days £403 Fri 13 Nov – Fri 27 Nov

Chicago → Punta Cana · Fri 13/11 · £150 Go

Punta Cana → Boston · Mon 23/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

9 + 5 days £403 Fri 13 Nov – Fri 27 Nov

Chicago → Punta Cana · Fri 13/11 · £150 Go

Punta Cana → Boston · Sun 22/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

8 + 6 days £403 Fri 13 Nov – Fri 27 Nov

Chicago → Punta Cana · Fri 13/11 · £150 Go

Punta Cana → Boston · Sat 21/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

12 + 2 days £403 Fri 13 Nov – Fri 27 Nov

Chicago → Punta Cana · Fri 13/11 · £150 Go

Punta Cana → Boston · Wed 25/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

4 + 7 days £409 Mon 16 Nov – Fri 27 Nov

Chicago → Punta Cana · Mon 16/11 · £143 Go

Punta Cana → Boston · Fri 20/11 · £169 Go

Boston → Chicago · Fri 27/11 · £97 Go

7 + 7 days £416 Fri 13 Nov – Fri 27 Nov

Chicago → Punta Cana · Fri 13/11 · £150 Go

Punta Cana → Boston · Fri 20/11 · £169 Go

Boston → Chicago · Fri 27/11 · £97 Go

5 + 8 days £433 Sat 14 Nov – Fri 27 Nov

Chicago → Punta Cana · Sat 14/11 · £180 Go

Punta Cana → Boston · Thu 19/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

7 + 6 days £433 Sat 14 Nov – Fri 27 Nov

Chicago → Punta Cana · Sat 14/11 · £180 Go

Punta Cana → Boston · Sat 21/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

9 + 4 days £433 Sat 14 Nov – Fri 27 Nov

Chicago → Punta Cana · Sat 14/11 · £180 Go

Punta Cana → Boston · Mon 23/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

10 + 3 days £433 Sat 14 Nov – Fri 27 Nov

Chicago → Punta Cana · Sat 14/11 · £180 Go

Punta Cana → Boston · Tue 24/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

11 + 2 days £433 Sat 14 Nov – Fri 27 Nov

Chicago → Punta Cana · Sat 14/11 · £180 Go

Punta Cana → Boston · Wed 25/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

8 + 5 days £433 Sat 14 Nov – Fri 27 Nov

Chicago → Punta Cana · Sat 14/11 · £180 Go

Punta Cana → Boston · Sun 22/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

6 + 7 days £446 Sat 14 Nov – Fri 27 Nov

Chicago → Punta Cana · Sat 14/11 · £180 Go

Punta Cana → Boston · Fri 20/11 · £169 Go

Boston → Chicago · Fri 27/11 · £97 Go

7 + 5 days £448 Sun 15 Nov – Fri 27 Nov

Chicago → Punta Cana · Sun 15/11 · £195 Go

Punta Cana → Boston · Sun 22/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

9 + 3 days £448 Sun 15 Nov – Fri 27 Nov

Chicago → Punta Cana · Sun 15/11 · £195 Go

Punta Cana → Boston · Tue 24/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

8 + 4 days £448 Sun 15 Nov – Fri 27 Nov

Chicago → Punta Cana · Sun 15/11 · £195 Go

Punta Cana → Boston · Mon 23/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

6 + 6 days £448 Sun 15 Nov – Fri 27 Nov

Chicago → Punta Cana · Sun 15/11 · £195 Go

Punta Cana → Boston · Sat 21/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

4 + 8 days £448 Sun 15 Nov – Fri 27 Nov

Chicago → Punta Cana · Sun 15/11 · £195 Go

Punta Cana → Boston · Thu 19/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

10 + 2 days £448 Sun 15 Nov – Fri 27 Nov

Chicago → Punta Cana · Sun 15/11 · £195 Go

Punta Cana → Boston · Wed 25/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

5 + 7 days £461 Sun 15 Nov – Fri 27 Nov

Chicago → Punta Cana · Sun 15/11 · £195 Go

Punta Cana → Boston · Fri 20/11 · £169 Go

Boston → Chicago · Fri 27/11 · £97 Go

7 + 3 days £475 Tue 17 Nov – Fri 27 Nov

Chicago → Punta Cana · Tue 17/11 · £222 Go

Punta Cana → Boston · Tue 24/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

2 + 8 days £475 Tue 17 Nov – Fri 27 Nov

Chicago → Punta Cana · Tue 17/11 · £222 Go

Punta Cana → Boston · Thu 19/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

4 + 6 days £475 Tue 17 Nov – Fri 27 Nov

Chicago → Punta Cana · Tue 17/11 · £222 Go

Punta Cana → Boston · Sat 21/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

5 + 5 days £475 Tue 17 Nov – Fri 27 Nov

Chicago → Punta Cana · Tue 17/11 · £222 Go

Punta Cana → Boston · Sun 22/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

6 + 4 days £475 Tue 17 Nov – Fri 27 Nov

Chicago → Punta Cana · Tue 17/11 · £222 Go

Punta Cana → Boston · Mon 23/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

8 + 2 days £475 Tue 17 Nov – Fri 27 Nov

Chicago → Punta Cana · Tue 17/11 · £222 Go

Punta Cana → Boston · Wed 25/11 · £156 Go

Boston → Chicago · Fri 27/11 · £97 Go

3 + 7 days £488 Tue 17 Nov – Fri 27 Nov

Chicago → Punta Cana · Tue 17/11 · £222 Go

Punta Cana → Boston · Fri 20/11 · £169 Go

Boston → Chicago · Fri 27/11 · £97 Go