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 14 days ago
406 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Aug 2, 2026.)
Today’s best flight deals from Cancún to Chicago
Explore current cheapest deals departing from Cancún to Chicago
2027-01-20 – 2027-01-22
CUN - Chicago
75% AI deal score
$366
$294
Round trip
2027-01-17 – 2027-01-22
CUN - Chicago
71% AI deal score
$358
$296
Round trip
2027-01-24 – 2027-01-28
CUN - Chicago
75% AI deal score
$365
$296
Round trip
2027-01-18 – 2027-01-22
CUN - Chicago
75% AI deal score
$361
$296
Round trip
2027-02-04 – 2027-02-15
CUN - Chicago
70% AI deal score
$349
$296
Round trip
2027-02-04 – 2027-02-20
CUN - Chicago
70% AI deal score
$345
$296
Round trip
2027-02-04 – 2027-02-22
CUN - Chicago
70% AI deal score
$345
$296
Round trip
2027-02-04 – 2027-02-12
CUN - Chicago
75% AI deal score
$358
$296
Round trip
2027-02-03 – 2027-02-15
CUN - Chicago
69% AI deal score
$338
$296
Round trip
2027-02-03 – 2027-02-20
CUN - Chicago
69% AI deal score
$336
$296
Round trip
