Flights from Chicago to Cancun

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.

Sat, Jul 5 - Fri, Jul 11

ORD

O'Hare Intl.

CUN

Cancun Intl.

$240 Roundtrip, found 2 days ago

$240

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Cancun Intl., returning Fri, Jul 11, priced at $240 found 2 days ago

Tue, Jun 10 - Sat, Jun 14

ORD

O'Hare Intl.

CUN

Cancun Intl.

$245 Roundtrip, found 1 day ago

$245

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Cancun Intl., returning Sat, Jun 14, priced at $245 found 1 day ago

Mon, Jul 7 - Fri, Jul 11

ORD

O'Hare Intl.

CUN

Cancun Intl.

$247 Roundtrip, found 2 days ago

$247

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Cancun Intl., returning Fri, Jul 11, priced at $247 found 2 days ago

Sat, Jul 5 - Tue, Jul 15

ORD

O'Hare Intl.

CUN

Cancun Intl.

$257 Roundtrip, found 2 days ago

$257

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Cancun Intl., returning Tue, Jul 15, priced at $257 found 2 days ago

Tue, Jul 8 - Fri, Jul 11

ORD

O'Hare Intl.

CUN

Cancun Intl.

$258 Roundtrip, found 2 days ago

$258

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Cancun Intl., returning Fri, Jul 11, priced at $258 found 2 days ago

Mon, Jun 16 - Wed, Jun 25

ORD

O'Hare Intl.

CUN

Cancun Intl.

$261 Roundtrip, found 6 days ago

$261

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Cancun Intl., returning Wed, Jun 25, priced at $261 found 6 days ago

Mon, Jul 7 - Tue, Jul 15

ORD

O'Hare Intl.

CUN

Cancun Intl.

$264 Roundtrip, found 2 days ago

$264

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Cancun Intl., returning Tue, Jul 15, priced at $264 found 2 days ago

Tue, Jun 10 - Sat, Jun 14

ORD

O'Hare Intl.

CUN

Cancun Intl.

$266 Roundtrip, found 1 day ago

$266

Roundtrip

found 1 day ago

Select Aeromexico flight, departing Tue, Jun 10 from O'Hare Intl. to Cancun Intl., returning Sat, Jun 14, priced at $266 found 1 day ago

Mon, Jul 7 - Mon, Jul 14

ORD

O'Hare Intl.

CUN

Cancun Intl.

$269 Roundtrip, found 2 days ago

$269

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Cancun Intl., returning Mon, Jul 14, priced at $269 found 2 days ago

Sat, Jun 14 - Wed, Jun 18

ORD

O'Hare Intl.

CUN

Cancun Intl.

$271 Roundtrip, found 2 days ago

$271

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Cancun Intl., returning Wed, Jun 18, priced at $271 found 2 days ago

Wed, Jul 9 - Fri, Jul 11

ORD

O'Hare Intl.

CUN

Cancun Intl.

$272 Roundtrip, found 2 days ago

$272

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Cancun Intl., returning Fri, Jul 11, priced at $272 found 2 days ago

Sun, Oct 19 - Tue, Oct 28

MDW

Midway Intl.

CUN

Cancun Intl.

$332 Roundtrip, found 4 days ago

$332

Roundtrip

found 4 days ago

Select Aeromexico flight, departing Sun, Oct 19 from Midway Intl. to Cancun Intl., returning Tue, Oct 28, priced at $332 found 4 days ago

Mon, Jun 9 - Wed, Jun 11

ORD

O'Hare Intl.

CUN

Cancun Intl.

$333 Roundtrip, found 2 hours ago

$333

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Cancun Intl., returning Wed, Jun 11, priced at $333 found 2 hours ago

Fri, Oct 24 - Sat, Oct 25

MDW

Midway Intl.

CUN

Cancun Intl.

$355 Roundtrip, found 4 days ago

$355

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Oct 24 from Midway Intl. to Cancun Intl., returning Sat, Oct 25, priced at $355 found 4 days ago

Mon, Jun 9 - Fri, Jun 13

ORD

O'Hare Intl.

CUN

Cancun Intl.

$366 Roundtrip, found 1 day ago

$366

Roundtrip

found 1 day ago

Select United flight, departing Mon, Jun 9 from O'Hare Intl. to Cancun Intl., returning Fri, Jun 13, priced at $366 found 1 day ago

Sat, Oct 25 - Sat, Oct 25

MDW

Midway Intl.

CUN

Cancun Intl.

$369 Roundtrip, found 4 days ago

$369

Roundtrip

found 4 days ago

Select Aeromexico flight, departing Sat, Oct 25 from Midway Intl. to Cancun Intl., returning Sat, Oct 25, priced at $369 found 4 days ago

Fri, Jun 6 - Sat, Jun 7

ORD

O'Hare Intl.

CUN

Cancun Intl.

$419 Roundtrip, found 2 hours ago

$419

Roundtrip

found 2 hours ago

Select Delta flight, departing Fri, Jun 6 from O'Hare Intl. to Cancun Intl., returning Sat, Jun 7, priced at $419 found 2 hours ago

Wed, Jun 4 - Thu, Jun 5

ORD

O'Hare Intl.

CUN

Cancun Intl.

$480 Roundtrip, found 2 hours ago

$480

Roundtrip

found 2 hours ago

Select Air Canada flight, departing Wed, Jun 4 from O'Hare Intl. to Cancun Intl., returning Thu, Jun 5, priced at $480 found 2 hours ago

Fri, Jun 6 - Sun, Jun 8

ORD

O'Hare Intl.

CUN

Cancun Intl.

$711 Roundtrip, found 2 hours ago

$711

Roundtrip

found 2 hours ago

Select Volaris flight, departing Fri, Jun 6 from O'Hare Intl. to Cancun Intl., returning Sun, Jun 8, priced at $711 found 2 hours ago

Fri, Jun 6 - Sun, Jun 8

ORD

O'Hare Intl.

CUN

Cancun Intl.

$1,106 Roundtrip, found 2 hours ago

$1,106

Roundtrip

found 2 hours ago

Select JetBlue Airways flight, departing Fri, Jun 6 from O'Hare Intl. to Cancun Intl., returning Sun, Jun 8, priced at $1,106 found 2 hours ago