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
457 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Sep 7, 2026.)
Today’s best flight deals from Cancún to Chicago
Explore current cheapest deals departing from Cancún to Chicago
2026-09-25 – 2026-09-29
CUN - Chicago
48% AI deal score
$370
$407
Round trip
2026-10-27 – 2026-11-03
CUN - Chicago
44% AI deal score
$332
$407
Round trip
2026-10-01 – 2026-10-04
CUN - Chicago
45% AI deal score
$349
$413
Round trip
2026-10-02 – 2026-10-05
CUN - Chicago
45% AI deal score
$348
$413
Round trip
2026-09-25 – 2026-09-30
CUN - Chicago
47% AI deal score
$355
$419
Round trip
2026-10-08 – 2026-10-12
CUN - Chicago
47% AI deal score
$402
$428
Round trip
2026-10-09 – 2026-10-13
CUN - Chicago
44% AI deal score
$346
$428
Round trip
2026-10-14 – 2026-10-28
CUN - Chicago
43% AI deal score
$300
$428
Round trip
2026-10-16 – 2026-10-19
CUN - Chicago
42% AI deal score
$261
$428
Round trip
2026-10-29 – 2026-11-02
CUN - Chicago
43% AI deal score
$344
$428
Round trip
