AirHint found the following cheapest return flights from Chicago (MDW) to Guadalajara (GDL) in October 2025 (see full year).

Return flights

08 Oct - 15 Oct	Volaris	direct
17 Oct - 20 Oct	Frontier Airlines
24 Oct - 31 Oct	Volaris	direct
23 Oct - 27 Oct	Frontier Airlines
10 Oct - 12 Oct	Frontier Airlines
10 Oct - 13 Oct	Frontier Airlines
13 Oct - 18 Oct	Frontier Airlines
23 Oct - 27 Oct	Frontier Airlines	direct
17 Oct - 26 Oct	Volaris
08 Oct - 11 Oct	Frontier Airlines

Also check the deals for one-way flights from Chicago to Guadalajara in October.

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 October from 309€

Return flights