Cheapest return flights from Cancun to Chicago in October from $155

AirHint found the following cheapest return flights from Cancun (CUN) to Chicago (ORD) in October 2025 (see full year).

Return flights

23 Oct - 28 Oct Frontier Airlines direct
11 Oct - 18 Oct Frontier Airlines direct
16 Oct - 19 Oct Frontier Airlines direct
23 Oct - 26 Oct Frontier Airlines direct
30 Oct - 04 Nov United direct
04 Oct - 10 Oct Spirit Airlines
04 Oct - 22 Oct Spirit Airlines
04 Oct - 11 Oct Spirit Airlines
04 Oct - 06 Oct Spirit Airlines
04 Oct - 21 Oct Spirit Airlines
11 Oct - 22 Oct Spirit Airlines
30 Oct - 03 Nov United direct
11 Oct - 01 Nov Spirit Airlines
25 Oct - 07 Nov Spirit Airlines
25 Oct - 08 Nov Spirit Airlines
25 Oct - 09 Nov Spirit Airlines
30 Oct - 07 Nov Spirit Airlines
30 Oct - 08 Nov Spirit Airlines
30 Oct - 09 Nov Spirit Airlines
22 Oct - 07 Nov Spirit Airlines

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

Skyscanner

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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.