Cheapest return flights from Chicago to Cancun in January from $268

AirHint found the following cheapest return flights from Chicago (MDW) to Cancun (CUN) in January 2026 (see full year).

Return flights

27 Jan - 06 Feb Southwest Airlines direct
11 Jan - 15 Jan Frontier Airlines
18 Jan - 26 Jan Frontier Airlines
11 Jan - 18 Jan Aeromexico
13 Jan - 18 Jan Aeromexico
24 Jan - 31 Jan Aeromexico
12 Jan - 18 Jan Aeromexico
05 Jan - 10 Jan Aeromexico
27 Jan - 31 Jan Aeromexico
13 Jan - 21 Jan Aeromexico
04 Jan - 10 Jan Aeromexico
28 Jan - 03 Feb Aeromexico
23 Jan - 06 Feb Aeromexico
28 Jan - 27 Feb Aeromexico
30 Jan - 02 Feb Aeromexico
29 Jan - 02 Feb Aeromexico
31 Jan - 02 Feb Aeromexico
31 Jan - 07 Feb Aeromexico
28 Jan - 01 Feb Frontier Airlines
30 Jan - 01 Feb Aeromexico

Also check the deals for one-way flights from Chicago to Cancun in January.

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