Chicago (ORD) to Cancún (CUN) flight deal in business from $405
$453 USD
-11%$405 USD
Verified 17 days agoOctober 2026
Mon
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Great Availability
61% of dates checked are available within 10% of the lowest price
Thursday, October 1st, 2026
Outbound Flights
13h 20m·1 stop
$444 USD
ORDOct 1 21:13
→AUSOct 1 23:59
AA 935Boeing 737
8h 1m layover·Overnight
AUSOct 2 08:00
→CUNOct 2 10:33
AA 2179Boeing 737
9h 56m·1 stop
$750 USDORDOct 1 05:00
→DFWOct 1 07:39
AA 760Airbus A321
4h 28m layover
DFWOct 1 12:07
→CUNOct 1 14:56
AA 2207Airbus A321
6h 9m·1 stop
$839 USDORDOct 1 05:00
→DFWOct 1 07:39
AA 760Airbus A321
41m layover
DFWOct 1 08:20
→CUNOct 1 11:09
AA 1190Airbus A321
5h 50m·1 stop
$839 USDORDOct 1 05:20
→CLTOct 1 08:27
AA 2842Airbus A321
43m layover
CLTOct 1 09:10
→CUNOct 1 11:10
AA 895Airbus A321
6h 8m·1 stop
$839 USDORDOct 1 06:59
→MIAOct 1 11:17
AA 1875Airbus A321
1h layover
MIAOct 1 12:17
→CUNOct 1 13:07
AA 2422Airbus A321
6h 41m·1 stop
$839 USDORDOct 1 08:15
→DFWOct 1 10:52
AA 1555Airbus A321
1h 15m layover
DFWOct 1 12:07
→CUNOct 1 14:56
AA 2207Airbus A321
13h 54m·1 stop
$839 USDORDOct 1 21:15
→DFWOct 1 23:37
AA 2281Airbus A321
8h 43m layover·Overnight
DFWOct 2 08:20
→CUNOct 2 11:09
AA 1190Airbus A321
3h 49m·Nonstop
$1,451 USDORDOct 1 10:11
→CUNOct 1 14:00
AA 492Boeing 737