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

Return flights

27 Jan - 11 Feb	Viva
24 Jan - 11 Feb	Viva
22 Jan - 11 Feb	Viva
31 Jan - 11 Feb	Viva
24 Jan - 30 Jan	Volaris
29 Jan - 11 Feb	Viva
15 Jan - 18 Jan	Viva
15 Jan - 19 Jan	Viva
17 Jan - 18 Jan	Viva
17 Jan - 19 Jan	Viva
27 Jan - 01 Feb	Viva
15 Jan - 01 Feb	Viva
24 Jan - 01 Feb	Viva
22 Jan - 01 Feb	Viva
17 Jan - 01 Feb	Viva
15 Jan - 25 Jan	Viva
24 Jan - 25 Jan	Viva
22 Jan - 25 Jan	Viva
17 Jan - 25 Jan	Viva
10 Jan - 18 Jan	Viva

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