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

Return flights

11 Jan - 15 Jan	Frontier Airlines
11 Jan - 16 Jan	Frontier Airlines
28 Jan - 03 Feb	Aeromexico
19 Jan - 22 Jan	Southwest Airlines
18 Jan - 24 Jan	Frontier Airlines
05 Jan - 12 Jan	Aeromexico
11 Jan - 18 Jan	Frontier Airlines
23 Jan - 28 Jan	Delta
02 Jan - 09 Jan	Frontier Airlines
17 Jan - 23 Jan	Delta
09 Jan - 16 Jan	Delta
02 Jan - 06 Feb	Delta
28 Jan - 01 Feb	Delta
31 Jan - 07 Feb	Frontier Airlines
31 Jan - 04 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 253€

Return flights