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

Return flights

27 Jan - 30 Jan	Southwest Airlines	direct
26 Jan - 30 Jan	Aeromexico
23 Jan - 29 Jan	Aeromexico
23 Jan - 30 Jan	Aeromexico
29 Jan - 02 Feb	Frontier Airlines
30 Jan - 03 Feb	Southwest Airlines
26 Jan - 29 Jan	Delta
21 Jan - 23 Jan	Delta
17 Jan - 21 Jan	Delta
18 Jan - 21 Jan	Delta
17 Jan - 23 Jan	Delta
18 Jan - 24 Jan	Delta
31 Jan - 03 Feb	Delta
31 Jan - 28 Feb	Delta
31 Jan - 02 Feb	Delta
30 Jan - 01 Feb	Frontier Airlines
29 Jan - 01 Feb	Frontier Airlines
28 Jan - 01 Feb	Southwest Airlines

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

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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Cheapest return flights from Chicago to Cancun in January from 258€

Return flights