Flights from Chicago to Punta Cana

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Nov 3 - Wed, Nov 5

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$338 Roundtrip, found 3 days ago

$338

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Nov 3 from O'Hare Intl. to Punta Cana Intl., returning Wed, Nov 5, priced at $338 found 3 days ago

Wed, Oct 29 - Wed, Nov 5

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$343 Roundtrip, found 3 days ago

$343

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Oct 29 from O'Hare Intl. to Punta Cana Intl., returning Wed, Nov 5, priced at $343 found 3 days ago

Sat, Nov 1 - Wed, Nov 5

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$356 Roundtrip, found 3 days ago

$356

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Nov 1 from O'Hare Intl. to Punta Cana Intl., returning Wed, Nov 5, priced at $356 found 3 days ago

Thu, Oct 30 - Wed, Nov 5

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$357 Roundtrip, found 3 days ago

$357

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Punta Cana Intl., returning Wed, Nov 5, priced at $357 found 3 days ago

Mon, Nov 3 - Thu, Nov 6

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$371 Roundtrip, found 3 days ago

$371

Roundtrip

found 3 days ago

Select Delta flight, departing Mon, Nov 3 from O'Hare Intl. to Punta Cana Intl., returning Thu, Nov 6, priced at $371 found 3 days ago

Sat, Nov 1 - Fri, Nov 7

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$375 Roundtrip, found 3 days ago

$375

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Nov 1 from O'Hare Intl. to Punta Cana Intl., returning Fri, Nov 7, priced at $375 found 3 days ago

Thu, Oct 30 - Fri, Nov 7

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$376 Roundtrip, found 3 days ago

$376

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Punta Cana Intl., returning Fri, Nov 7, priced at $376 found 3 days ago

Wed, Oct 29 - Sat, Nov 8

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$379 Roundtrip, found 3 days ago

$379

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Oct 29 from O'Hare Intl. to Punta Cana Intl., returning Sat, Nov 8, priced at $379 found 3 days ago

Sat, Nov 1 - Thu, Nov 6

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$393 Roundtrip, found 3 days ago

$393

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Nov 1 from O'Hare Intl. to Punta Cana Intl., returning Thu, Nov 6, priced at $393 found 3 days ago

Thu, Oct 30 - Sat, Nov 8

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$404 Roundtrip, found 3 days ago

$404

Roundtrip

found 3 days ago

Select Delta flight, departing Thu, Oct 30 from O'Hare Intl. to Punta Cana Intl., returning Sat, Nov 8, priced at $404 found 3 days ago

Wed, Oct 29 - Mon, Nov 10

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$413 Roundtrip, found 3 days ago

$413

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Oct 29 from O'Hare Intl. to Punta Cana Intl., returning Mon, Nov 10, priced at $413 found 3 days ago

Sat, Nov 1 - Sat, Nov 8

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$415 Roundtrip, found 3 days ago

$415

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Nov 1 from O'Hare Intl. to Punta Cana Intl., returning Sat, Nov 8, priced at $415 found 3 days ago

Sun, Nov 2 - Thu, Nov 6

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$420 Roundtrip, found 3 days ago

$420

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sun, Nov 2 from O'Hare Intl. to Punta Cana Intl., returning Thu, Nov 6, priced at $420 found 3 days ago

Sun, Nov 2 - Tue, Nov 11

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$443 Roundtrip, found 3 days ago

$443

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Nov 2 from O'Hare Intl. to Punta Cana Intl., returning Tue, Nov 11, priced at $443 found 3 days ago

Wed, Dec 31 - Wed, Jan 7

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$585 Roundtrip, found 1 day ago

$585

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Dec 31 from O'Hare Intl. to Punta Cana Intl., returning Wed, Jan 7, priced at $585 found 1 day ago

Tue, Dec 30 - Wed, Jan 7

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$590 Roundtrip, found 1 day ago

$590

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Dec 30 from O'Hare Intl. to Punta Cana Intl., returning Wed, Jan 7, priced at $590 found 1 day ago

Mon, Dec 29 - Wed, Jan 7

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$597 Roundtrip, found 1 day ago

$597

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Mon, Dec 29 from O'Hare Intl. to Punta Cana Intl., returning Wed, Jan 7, priced at $597 found 1 day ago

Tue, Dec 30 - Tue, Jan 6

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$605 Roundtrip, found 1 day ago

$605

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Dec 30 from O'Hare Intl. to Punta Cana Intl., returning Tue, Jan 6, priced at $605 found 1 day ago

Thu, Jan 1 - Thu, Jan 1

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$762 Roundtrip, found 1 day ago

$762

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Jan 1 from O'Hare Intl. to Punta Cana Intl., returning Thu, Jan 1, priced at $762 found 1 day ago

Tue, Dec 30 - Sun, Jan 4

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$1,179 Roundtrip, found 1 day ago

$1,179

Roundtrip

found 1 day ago

Select United flight, departing Tue, Dec 30 from O'Hare Intl. to Punta Cana Intl., returning Sun, Jan 4, priced at $1,179 found 1 day ago