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

Return flights

14 Jan - 19 Jan	Volaris
25 Jan - 12 Feb	Volaris
11 Jan - 20 Feb	Volaris	direct
02 Jan - 20 Feb	Aeromexico
16 Jan - 23 Jan	Volaris	direct
14 Jan - 20 Jan	Volaris
16 Jan - 19 Jan	Volaris
15 Jan - 22 Jan	Frontier Airlines
16 Jan - 25 Jan	Volaris	direct
29 Jan - 02 Feb	Frontier Airlines
24 Jan - 15 Feb	Frontier Airlines
06 Jan - 18 Jan	Frontier Airlines
03 Jan - 13 Jan	Frontier Airlines
05 Jan - 13 Feb	Aeromexico
22 Jan - 26 Jan	Aeromexico
15 Jan - 19 Jan	Frontier Airlines
30 Jan - 16 Feb	Volaris	direct
02 Jan - 13 Feb	Aeromexico
02 Jan - 13 Feb	Volaris	direct
05 Jan - 13 Feb	Volaris	direct

Also check the deals for one-way flights from Chicago to Guadalajara 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 Guadalajara in January from $332

Return flights