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, Apr 10 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$194 Roundtrip, found 13 hours ago
$194
Roundtrip
found 13 hours ago
Wed, Apr 10 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$196 Roundtrip, found 13 hours ago
$196
Roundtrip
found 13 hours ago
Tue, Apr 2 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$202 Roundtrip, found 2 hours ago
$202
Roundtrip
found 2 hours ago
Wed, May 8 - Fri, May 10
ORD
O'Hare Intl.
CUN
Cancun Intl.
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Fri, Apr 5 - Tue, Apr 9
ORD
O'Hare Intl.
CUN
Cancun Intl.
$213 Roundtrip, found 11 hours ago
$213
Roundtrip
found 11 hours ago
Fri, Apr 5 - Tue, Apr 9
ORD
O'Hare Intl.
CUN
Cancun Intl.
$214 Roundtrip, found 11 hours ago
$214
Roundtrip
found 11 hours ago
Sat, Apr 20 - Wed, Apr 24
ORD
O'Hare Intl.
CUN
Cancun Intl.
$216 Roundtrip, found 5 days ago
$216
Roundtrip
found 5 days ago
Fri, Apr 26 - Thu, May 2
ORD
O'Hare Intl.
CUN
Cancun Intl.
$216 Roundtrip, found 13 hours ago
$216
Roundtrip
found 13 hours ago
Fri, May 10 - Thu, May 16
ORD
O'Hare Intl.
CUN
Cancun Intl.
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Sat, May 11 - Thu, May 16
ORD
O'Hare Intl.
CUN
Cancun Intl.
$221 Roundtrip, found 2 days ago
$221
Roundtrip
found 2 days ago
Tue, Apr 2 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$221 Roundtrip, found 2 hours ago
$221
Roundtrip
found 2 hours ago
Tue, Apr 2 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$234 Roundtrip, found 2 hours ago
$234
Roundtrip
found 2 hours ago
Tue, Apr 2 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$261 Roundtrip, found 2 hours ago
$261
Roundtrip
found 2 hours ago
Sat, May 11 - Thu, May 16
MDW
Midway Intl.
CUN
Cancun Intl.
$335 Roundtrip, found 3 days ago
$335
Roundtrip
found 3 days ago
Sun, May 12 - Sat, May 18
ORD
O'Hare Intl.
CZM
Cozumel Intl.
$370 Roundtrip, found 23 hours ago
$370
Roundtrip
found 23 hours ago
Tue, Apr 2 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$384 Roundtrip, found 2 hours ago
$384
Roundtrip
found 2 hours ago
Tue, Apr 2 - Thu, Apr 11
ORD
O'Hare Intl.
CUN
Cancun Intl.
$389 Roundtrip, found 2 hours ago
$389
Roundtrip
found 2 hours ago
Fri, May 10 - Mon, May 13
ORD
O'Hare Intl.
CUN
Cancun Intl.
$414 Roundtrip, found 2 days ago
$414
Roundtrip
found 2 days ago
Sun, Apr 21 - Thu, Apr 25
ORD
O'Hare Intl.
CUN
Cancun Intl.
$538 Roundtrip, found 4 days ago
$538
Roundtrip
found 4 days ago
Thu, Aug 1 - Mon, Aug 5
ORD
O'Hare Intl.
CUN
Cancun Intl.
$867 Roundtrip, found 6 days ago
$867
Roundtrip
found 6 days ago