Cheap Flights from Cancún to Chicago
Browse current best options from Cancún. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Cancún
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 5 days ago
481 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Oct 19, 2026.)
Today’s best flight deals from Cancún to Chicago
Explore current cheapest deals departing from Cancún to Chicago
2026-10-22 – 2026-10-28
CUN - Chicago
70% AI deal score
$425
$391
Round trip
2026-10-22 – 2026-10-27
CUN - Chicago
72% AI deal score
$461
$394
Round trip
2026-10-21 – 2026-10-26
CUN - Chicago
73% AI deal score
$470
$397
Round trip
2026-10-21 – 2026-10-28
CUN - Chicago
70% AI deal score
$433
$397
Round trip
2026-10-22 – 2026-10-31
CUN - Chicago
41% AI deal score
$296
$409
Round trip
2026-10-24 – 2026-10-31
CUN - Chicago
41% AI deal score
$320
$409
Round trip
2026-10-22 – 2026-10-29
CUN - Chicago
69% AI deal score
$425
$409
Round trip
2026-10-20 – 2026-10-25
CUN - Chicago
41% AI deal score
$358
$411
Round trip
2026-10-20 – 2026-10-27
CUN - Chicago
41% AI deal score
$324
$411
Round trip
2026-10-23 – 2026-10-28
CUN - Chicago
41% AI deal score
$353
$412
Round trip
