Cheapest return flights from Montreal to Chicago in October from $322

AirHint found the following cheapest return flights from Montreal (YUL) to Chicago (MDW) in October 2026 (see full year).

Return flights

09 Oct - 14 Oct Delta
07 Oct - 14 Oct WestJet
02 Oct - 09 Oct WestJet
04 Oct - 11 Oct WestJet
06 Oct - 13 Oct WestJet
08 Oct - 15 Oct WestJet
09 Oct - 16 Oct WestJet
10 Oct - 17 Oct WestJet
12 Oct - 19 Oct WestJet
14 Oct - 21 Oct WestJet
25 Oct - 01 Nov WestJet
26 Oct - 02 Nov WestJet
28 Oct - 04 Nov WestJet
29 Oct - 05 Nov WestJet
30 Oct - 06 Nov WestJet
31 Oct - 07 Nov WestJet

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

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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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