Chicago (ORD) to Cancún (CUN) flight deal in business from $405
$453 USD
-11%$405 USD
Verified 17 days agoSeptember 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Great Availability
61% of dates checked are available within 10% of the lowest price
Wednesday, September 23rd, 2026
Outbound Flights
7h 7m·1 stop
$460 USD
ORDSep 23 06:00
→MIASep 23 10:17
AA 2452Boeing 737MAX 8 Passenger
2h layover
MIASep 23 12:17
→CUNSep 23 13:07
AA 2422Airbus A321
17h 34m·1 stop
$496 USDORDSep 23 21:01
→CLTSep 24 00:04
AA 2976Airbus A321
12h 36m layover
CLTSep 24 12:40
→CUNSep 24 14:35
AA 1778Airbus A321
6h 7m·1 stop
$562 USDORDSep 23 05:00
→DFWSep 23 07:39
AA 760Airbus A321
41m layover
DFWSep 23 08:20
→CUNSep 23 11:07
AA 1190Boeing 737
6h 8m·1 stop
$562 USDORDSep 23 06:59
→MIASep 23 11:17
AA 1875Airbus A321
1h layover
MIASep 23 12:17
→CUNSep 23 13:07
AA 2422Airbus A321
18h 7m·1 stop
$577 USDORDSep 23 19:00
→MIASep 23 23:15
AA 1159Airbus A321
13h 2m layover·Overnight
MIASep 24 12:17
→CUNSep 24 13:07
AA 2422Airbus A321
3h 49m·Nonstop
$740 USDORDSep 23 10:11
→CUNSep 23 14:00
AA 492Boeing 737
5h 50m·1 stop
$3,100 USDORDSep 23 05:20
→CLTSep 23 08:27
AA 2842Airbus A321
43m layover
CLTSep 23 09:10
→CUNSep 23 11:10
AA 895Airbus A321