Chicago (ORD) to Cancún (CUN) flight deal in business from $405
$453 USD
-11%$405 USD
Verified 17 days agoSeptember 2026
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Great Availability
61% of dates checked are available within 10% of the lowest price
Sunday, September 27th, 2026
Outbound Flights
6h 43m·1 stop
$416 USD
ORDSep 27 08:42
→MIASep 27 12:59
AA 1250Airbus A321
1h 39m layover
MIASep 27 14:38
→CUNSep 27 15:25
AA 158Boeing 737
8h 57m·1 stop
$416 USDORDSep 27 05:00
→DFWSep 27 07:39
AA 760Airbus A321
3h 32m layover
DFWSep 27 11:11
→CUNSep 27 13:57
AA 1547Boeing 737
12h 45m·1 stop
$416 USDORDSep 27 21:15
→DFWSep 27 23:37
AA 2281Airbus A321
7h 36m layover·Overnight
DFWSep 28 07:13
→CUNSep 28 10:00
AA 1752Boeing 737
3h 49m·Nonstop
$553 USDORDSep 27 10:11
→CUNSep 27 14:00
AA 492Boeing 737
5h 51m·1 stop
$557 USDORDSep 27 05:18
→CLTSep 27 08:25
AA 2842Airbus A321
45m layover
CLTSep 27 09:10
→CUNSep 27 11:09
AA 895Airbus A321