Flights from Chicago to Cancun

Our cheapest offers for flights from Chicago to Cancun

Here you can compare cheap flights from Chicago (CHI) to Cancun (CUN) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Cancun. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Best option
Chicago
Cancun
Outbound
02/13/26
1 Stopover (MEX)
Y40703, Y40102
14h 03min
Return
02/26/26
direct
NK0105
04h 08min
Volaris
$270
Chicago
Cancun
Outbound
01/14/26
1 Stopover (CLT)
AA1784, AA0886
06h 15min
Return
01/18/26
direct
AA0215
04h 05min
American Airlines
$940
Chicago
Cancun
Please note: transfer for connecting flight
Outbound
01/14/26
1 Stopover (MEX)
AM0689, AM0536
16h 26min
Return
01/18/26
1 Stopover (MEX)
AM0561, AM0682
26h 49min
Aeroméxico
$1,300
Chicago
Cancun
Outbound
02/13/26
1 Stopover (MEX)
Y40701, Y40104
14h 03min
Return
02/26/26
direct
NK0105
04h 08min
Volaris
$271
Chicago
Cancun
Outbound
04/03/26
1 Stopover (MEX)
Y40701, Y40104
13h 23min
Return
04/16/26
1 Stopover (MEX)
Y40105, Y40700
08h 07min
Volaris ?
$272
Chicago
Cancun
Outbound
04/03/26
1 Stopover (MEX)
Y40701, Y40104
13h 23min
Return
04/16/26
1 Stopover (MEX)
Y40103, Y40700
14h 37min
Volaris
$274
Chicago
Cancun
Outbound
04/03/26
1 Stopover (MEX)
Y40701, Y40104
13h 23min
Return
04/16/26
1 Stopover (MEX)
Y40103, Y40700
14h 37min
Volaris
$275
Chicago
Cancun
Outbound
01/14/26
1 Stopover (MEX)
Y40703, Y40100
08h 53min
Return
01/18/26
1 Stopover (PUJ)
DM7005, DM5420
10h 15min
Volaris
$338
Chicago
Cancun
Outbound
02/13/26
1 Stopover (MEX)
AM0687, AM0562
09h 26min
Return
02/26/26
direct
UA1423
03h 51min
Aeroméxico ?
$355
Chicago
Cancun
Outbound
02/13/26
1 Stopover (MEX)
AM0687, AM0562
09h 26min
Return
02/26/26
direct
NK0105
04h 08min
Aeroméxico ?
$364
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to Cancun

Favorite airline: Aeroméxico
Most travelers looking for flights on the route from Chicago to Cancun decide to book flights with Aeroméxico.
Aeroméxico
50 %
Spirit Airlines
25 %
Frontier Airlines
8 %
Direct flights are cheaper
Compared to flights with a stopover, direct flights are $81.00 cheaper on this route.
non stop flight
1 stop
04h 14min
09h 39min
$ 207
$ 288
Favourite connection: via Mexico City
On this route, flights with a stopover in Mexico City are the most popular.
Route
bookings
1 stopover Mexico City-Juarez International
09h 39min, from $ 288
65 %
Direct flights
04h 14min, from $ 207
19 %
1 stopover Hartsfield-Jackson Atlanta International Airport, GA
06h 56min, from $ 320
5 %

Important flight information

Flight information: Chicago - Cancun

Roundtrip from $ 270,00
Flight duration min. 03:39 / max. 03:58
Return flight duration min. 03:40/ max. 04:04
Distance 2322 km
Flights per week 67
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport Cancun (CUN)
Destination country Flights to Mexico
Alternative routes to Mexico
Alternative flights to Cancun
Flight destinations with a similar price
Flight destinations with a similar price