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.

Wed, Jun 11 - Tue, Jun 17

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$345 Roundtrip, found 2 hours ago

$345

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Jun 11 from O'Hare Intl. to Punta Cana Intl., returning Tue, Jun 17, priced at $345 found 2 hours ago

Wed, Jun 11 - Sat, Jun 14

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$367 Roundtrip, found 2 hours ago

$367

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Jun 11 from O'Hare Intl. to Punta Cana Intl., returning Sat, Jun 14, priced at $367 found 2 hours ago

Wed, Jun 11 - Thu, Jun 19

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$374 Roundtrip, found 2 hours ago

$374

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Jun 11 from O'Hare Intl. to Punta Cana Intl., returning Thu, Jun 19, priced at $374 found 2 hours ago

Tue, Jun 10 - Tue, Jun 17

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$379 Roundtrip, found 2 hours ago

$379

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Punta Cana Intl., returning Tue, Jun 17, priced at $379 found 2 hours ago

Sat, Jun 14 - Tue, Jun 17

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$388 Roundtrip, found 2 hours ago

$388

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Punta Cana Intl., returning Tue, Jun 17, priced at $388 found 2 hours ago

Sun, Jun 15 - Tue, Jun 17

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$394 Roundtrip, found 2 hours ago

$394

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Sun, Jun 15 from O'Hare Intl. to Punta Cana Intl., returning Tue, Jun 17, priced at $394 found 2 hours ago

Sat, Jun 14 - Mon, Jun 16

MDW

Midway Intl.

PUJ

Punta Cana Intl.

$395 Roundtrip, found 2 hours ago

$395

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Sat, Jun 14 from Midway Intl. to Punta Cana Intl., returning Mon, Jun 16, priced at $395 found 2 hours ago

Wed, Jun 11 - Sun, Jun 15

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$399 Roundtrip, found 2 hours ago

$399

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Jun 11 from O'Hare Intl. to Punta Cana Intl., returning Sun, Jun 15, priced at $399 found 2 hours ago

Tue, Jun 10 - Sat, Jun 14

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$401 Roundtrip, found 2 hours ago

$401

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Punta Cana Intl., returning Sat, Jun 14, priced at $401 found 2 hours ago

Wed, Jun 11 - Wed, Jun 18

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$402 Roundtrip, found 2 hours ago

$402

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Jun 11 from O'Hare Intl. to Punta Cana Intl., returning Wed, Jun 18, priced at $402 found 2 hours ago

Tue, Jun 10 - Thu, Jun 12

MDW

Midway Intl.

PUJ

Punta Cana Intl.

$402 Roundtrip, found 2 hours ago

$402

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Tue, Jun 10 from Midway Intl. to Punta Cana Intl., returning Thu, Jun 12, priced at $402 found 2 hours ago

Sat, Jun 14 - Wed, Jun 18

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$410 Roundtrip, found 2 hours ago

$410

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Punta Cana Intl., returning Wed, Jun 18, priced at $410 found 2 hours ago

Sat, Jun 14 - Mon, Jun 16

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$412 Roundtrip, found 2 hours ago

$412

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Punta Cana Intl., returning Mon, Jun 16, priced at $412 found 2 hours ago

Tue, Jun 10 - Fri, Jun 13

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$415 Roundtrip, found 2 hours ago

$415

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Punta Cana Intl., returning Fri, Jun 13, priced at $415 found 2 hours ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$473 Roundtrip, found 2 hours ago

$473

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Thu, Jun 12 from O'Hare Intl. to Punta Cana Intl., returning Mon, Jun 16, priced at $473 found 2 hours ago

Fri, Jun 13 - Fri, Jun 13

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$474 Roundtrip, found 2 hours ago

$474

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Fri, Jun 13 from O'Hare Intl. to Punta Cana Intl., returning Fri, Jun 13, priced at $474 found 2 hours ago

Wed, Jun 11 - Sat, Jun 14

MDW

Midway Intl.

PUJ

Punta Cana Intl.

$610 Roundtrip, found 2 hours ago

$610

Roundtrip

found 2 hours ago

Select Delta flight, departing Wed, Jun 11 from Midway Intl. to Punta Cana Intl., returning Sat, Jun 14, priced at $610 found 2 hours ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$948 Roundtrip, found 2 hours ago

$948

Roundtrip

found 2 hours ago

Select United flight, departing Thu, Jun 12 from O'Hare Intl. to Punta Cana Intl., returning Mon, Jun 16, priced at $948 found 2 hours ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$1,456 Roundtrip, found 2 hours ago

$1,456

Roundtrip

found 2 hours ago

Select Copa flight, departing Thu, Jun 12 from O'Hare Intl. to Punta Cana Intl., returning Mon, Jun 16, priced at $1,456 found 2 hours ago

Thu, Jun 12 - Mon, Jun 16

ORD

O'Hare Intl.

PUJ

Punta Cana Intl.

$3,743 Roundtrip, found 2 hours ago

$3,743

Roundtrip

found 2 hours ago

Select Air Canada flight, departing Thu, Jun 12 from O'Hare Intl. to Punta Cana Intl., returning Mon, Jun 16, priced at $3,743 found 2 hours ago