Flights from Chicago to Riviera Maya

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, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$213 Roundtrip, found 23 hours ago

$213

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $213 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$218 Roundtrip, found 23 hours ago

$218

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $218 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$227 Roundtrip, found 23 hours ago

$227

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $227 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$232 Roundtrip, found 23 hours ago

$232

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $232 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$232 Roundtrip, found 23 hours ago

$232

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $232 found 23 hours ago

Tue, Sep 16 - Sat, Sep 20

ORD

O'Hare Intl.

CUN

Cancun Intl.

$235 Roundtrip, found 3 days ago

$235

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Sep 16 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 20, priced at $235 found 3 days ago

Tue, Sep 16 - Sun, Sep 21

ORD

O'Hare Intl.

CUN

Cancun Intl.

$239 Roundtrip, found 3 days ago

$239

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Sep 16 from O'Hare Intl. to Cancun Intl., returning Sun, Sep 21, priced at $239 found 3 days ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$245 Roundtrip, found 23 hours ago

$245

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $245 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$246 Roundtrip, found 23 hours ago

$246

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $246 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$247 Roundtrip, found 23 hours ago

$247

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $247 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$250 Roundtrip, found 23 hours ago

$250

Roundtrip

found 23 hours ago

Select United flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $250 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$271 Roundtrip, found 23 hours ago

$271

Roundtrip

found 23 hours ago

Select United flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $271 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$326 Roundtrip, found 23 hours ago

$326

Roundtrip

found 23 hours ago

Select Delta flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $326 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$326 Roundtrip, found 23 hours ago

$326

Roundtrip

found 23 hours ago

Select Aeromexico flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $326 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$366 Roundtrip, found 23 hours ago

$366

Roundtrip

found 23 hours ago

Select American Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $366 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$443 Roundtrip, found 23 hours ago

$443

Roundtrip

found 23 hours ago

Select Volaris flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $443 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$483 Roundtrip, found 23 hours ago

$483

Roundtrip

found 23 hours ago

Select Viva flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $483 found 23 hours ago

Sat, Aug 23 - Sat, Sep 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$564 Roundtrip, found 23 hours ago

$564

Roundtrip

found 23 hours ago

Select Air Canada flight, departing Sat, Aug 23 from O'Hare Intl. to Cancun Intl., returning Sat, Sep 6, priced at $564 found 23 hours ago

Mon, Dec 22 - Tue, Jan 6

ORD

O'Hare Intl.

CUN

Cancun Intl.

$742 Roundtrip, found 5 days ago

$742

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Mon, Dec 22 from O'Hare Intl. to Cancun Intl., returning Tue, Jan 6, priced at $742 found 5 days ago

Sat, Dec 20 - Thu, Jan 1

MDW

Midway Intl.

CUN

Cancun Intl.

$832 Roundtrip, found 5 days ago

$832

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, Dec 20 from Midway Intl. to Cancun Intl., returning Thu, Jan 1, priced at $832 found 5 days ago