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Outbound flight: 12/31/21
06:55 CHI
22:04 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 01/11/22
21:58 CUN
09:32 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$242
Check
Outbound flight: 12/31/21
06:55 CHI
22:04 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 01/11/22
21:58 CUN
09:32 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$242
Check
Outbound flight: 12/31/21
22:03 CHI
10:47 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 01/11/22
21:58 CUN
09:32 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$266
Check
Outbound flight: 12/31/21
22:03 CHI
10:47 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 01/11/22
21:58 CUN
09:32 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$266
Check
Outbound flight: 08/14/21
23:55 CHI
08:15 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
Viva Aerobus
Return flight: 08/29/21
10:15 CUN
23:45 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Viva Aerobus
$274
Check
Outbound flight: 08/14/21
23:55 CHI
08:15 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
Viva Aerobus
Return flight: 08/29/21
10:15 CUN
23:45 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
Viva Aerobus
$274
Check
Outbound flight: 08/07/21
17:50 CHI
09:45 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 08/10/21
11:35 CUN
15:50 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$274
Check
Outbound flight: 08/07/21
09:30 CHI
19:45 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 08/10/21
11:35 CUN
15:50 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$276
Check
Outbound flight: 08/07/21
17:00 CHI
23:35 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 08/10/21
11:35 CUN
15:50 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
direct
American Airlines
$276
Check
Outbound flight: 08/07/21
17:50 CHI
09:45 CUN
Chicago-IL all Airports (ORD, MDW, RFD)
Cancun
1 Stopover
American Airlines
Return flight: 08/10/21
06:10 CUN
15:05 CHI
Cancun
Chicago-IL all Airports (ORD, MDW, RFD)
1 Stopover
American Airlines
$279
Check
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: United Airlines
The favorite airline for flights from Chicago to Cancun is United Airlines.
United Airlines
18 %
Spirit Airlines
9 %
American Airlines
6 %
Direct flights are the cheapest connection
On this route, direct flights are $29.00 cheaper than flights with a stopover.
non stop flight
1 stop
03h 42min
17h 05min
$213
$242
The favorite connection is non-stop
39 % of all bookings on the route Chicago to Cancun are for non-stop flights.
Route
bookings
Direct flights
03h 42min, from $213
39 %
1 stopover Mexico City-Juarez International
08h 14min, from $251
14 %
1 stopover Dallas-Fort Worth International Airport, T
15h 35min, from $244
12 %
Flight information Chicago - Cancun
Alternative flight routes
Cheap direct flights
Flight details Chicago - Cancun
  • Flight duration: min. 03:39 / max. 03:58
  • Distance: 2322 km
  • Flights per week: 67
  • Return flight duration: min. 03:40 / max. 04:04
Top Flight Routes
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.