Punta Cana & Orlando

Both destinations in one trip from Chicago

£393 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.

Orlando

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

8 + 3 days £393 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 24/11 · £130 Go

Orlando → Chicago · Fri 27/11 · £120 Go

4 + 7 days £399 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Fri 20/11 · £136 Go

Orlando → Chicago · Fri 27/11 · £120 Go

11 + 3 days £400 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 24/11 · £130 Go

Orlando → Chicago · Fri 27/11 · £120 Go

6 + 5 days £404 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sun 22/11 · £141 Go

Orlando → Chicago · Fri 27/11 · £120 Go

7 + 7 days £406 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Fri 20/11 · £136 Go

Orlando → Chicago · Fri 27/11 · £120 Go

9 + 5 days £411 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sun 22/11 · £141 Go

Orlando → Chicago · Fri 27/11 · £120 Go

4 + 10 days £430 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 17/11 · £160 Go

Orlando → Chicago · Fri 27/11 · £120 Go

10 + 3 days £430 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 24/11 · £130 Go

Orlando → Chicago · Fri 27/11 · £120 Go

6 + 7 days £436 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Fri 20/11 · £136 Go

Orlando → Chicago · Fri 27/11 · £120 Go

8 + 5 days £441 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sun 22/11 · £141 Go

Orlando → Chicago · Fri 27/11 · £120 Go

9 + 3 days £445 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 24/11 · £130 Go

Orlando → Chicago · Fri 27/11 · £120 Go

2 + 12 days £446 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sun 15/11 · £176 Go

Orlando → Chicago · Fri 27/11 · £120 Go

5 + 7 days £451 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Fri 20/11 · £136 Go

Orlando → Chicago · Fri 27/11 · £120 Go

7 + 5 days £456 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sun 22/11 · £141 Go

Orlando → Chicago · Fri 27/11 · £120 Go

5 + 6 days £459 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sat 21/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

3 + 8 days £459 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Thu 19/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

7 + 4 days £459 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Mon 23/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

3 + 10 days £460 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 17/11 · £160 Go

Orlando → Chicago · Fri 27/11 · £120 Go

9 + 2 days £465 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Wed 25/11 · £202 Go

Orlando → Chicago · Fri 27/11 · £120 Go

10 + 4 days £466 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Mon 23/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

8 + 6 days £466 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sat 21/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

6 + 8 days £466 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Thu 19/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

2 + 9 days £471 Mon 16 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Wed 18/11 · £208 Go

Orlando → Chicago · Fri 27/11 · £120 Go

7 + 3 days £472 Tue 17 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 24/11 · £130 Go

Orlando → Chicago · Fri 27/11 · £120 Go

12 + 2 days £472 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Wed 25/11 · £202 Go

Orlando → Chicago · Fri 27/11 · £120 Go

2 + 10 days £475 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Tue 17/11 · £160 Go

Orlando → Chicago · Fri 27/11 · £120 Go

5 + 9 days £478 Fri 13 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Wed 18/11 · £208 Go

Orlando → Chicago · Fri 27/11 · £120 Go

3 + 7 days £478 Tue 17 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Fri 20/11 · £136 Go

Orlando → Chicago · Fri 27/11 · £120 Go

5 + 5 days £483 Tue 17 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sun 22/11 · £141 Go

Orlando → Chicago · Fri 27/11 · £120 Go

9 + 4 days £496 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Mon 23/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

7 + 6 days £496 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sat 21/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

5 + 8 days £496 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Thu 19/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

11 + 2 days £502 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Wed 25/11 · £202 Go

Orlando → Chicago · Fri 27/11 · £120 Go

4 + 9 days £508 Sat 14 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Wed 18/11 · £208 Go

Orlando → Chicago · Fri 27/11 · £120 Go

8 + 4 days £511 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Mon 23/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

4 + 8 days £511 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Thu 19/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

6 + 6 days £511 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Sat 21/11 · £196 Go

Orlando → Chicago · Fri 27/11 · £120 Go

10 + 2 days £517 Sun 15 Nov – Fri 27 Nov

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

Punta Cana → Orlando · Wed 25/11 · £202 Go

Orlando → Chicago · Fri 27/11 · £120 Go