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
Wednesday, September 16th, 2026
Outbound Flights
18h 7m·1 stop
$478 USD
ORDSep 16 19:00
→MIASep 16 23:15
AA 1159Airbus A321
13h 2m layover·Overnight
MIASep 17 12:17
→CUNSep 17 13:07
AA 2422Airbus A321
14h 9m·1 stop
$607 USDORDSep 16 21:01
→CLTSep 17 00:04
AA 2976Airbus A321
9h 6m layover
CLTSep 17 09:10
→CUNSep 17 11:10
AA 895Airbus A321
3h 49m·Nonstop
$912 USDORDSep 16 10:11
→CUNSep 16 14:00
AA 492Boeing 737
6h 34m·1 stop
$1,502 USDORDSep 16 05:00
→MIASep 16 09:14
AA 2984Boeing 737
1h 26m layover
MIASep 16 10:40
→CUNSep 16 11:34
AA 1157Airbus A321neo
6h 8m·1 stop
$1,502 USDORDSep 16 06:59
→MIASep 16 11:17
AA 1875Airbus A321
1h layover
MIASep 16 12:17
→CUNSep 16 13:07
AA 2422Airbus A321
6h 7m·1 stop
$1,651 USDORDSep 16 05:00
→DFWSep 16 07:39
AA 760Airbus A321
41m layover
DFWSep 16 08:20
→CUNSep 16 11:07
AA 1190Boeing 737
5h 50m·1 stop
$2,073 USDORDSep 16 05:20
→CLTSep 16 08:27
AA 2842Airbus A321
43m layover
CLTSep 16 09:10
→CUNSep 16 11:10
AA 895Airbus A321