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 2 days ago
476 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Oct 12, 2026.)
Today’s best flight deals from Cancún to Chicago
Explore current cheapest deals departing from Cancún to Chicago
2027-01-25 – 2027-01-28
CUN - Chicago
80% AI deal score
$336
$236
Round trip
2027-01-25 – 2027-01-30
CUN - Chicago
79% AI deal score
$336
$241
Round trip
2027-01-27 – 2027-01-30
CUN - Chicago
79% AI deal score
$338
$241
Round trip
2026-12-14 – 2027-01-12
CUN - Chicago
77% AI deal score
$327
$254
Round trip
2027-01-16 – 2027-01-28
CUN - Chicago
49% AI deal score
$292
$292
Round trip
2027-02-20 – 2027-02-28
CUN - Chicago
67% AI deal score
$317
$292
Round trip
2027-02-13 – 2027-02-28
CUN - Chicago
49% AI deal score
$295
$292
Round trip
2027-02-24 – 2027-02-28
CUN - Chicago
68% AI deal score
$321
$292
Round trip
2027-01-20 – 2027-01-28
CUN - Chicago
67% AI deal score
$315
$293
Round trip
2027-01-13 – 2027-01-28
CUN - Chicago
48% AI deal score
$283
$293
Round trip
