Cheapest return flights from Montreal to Chicago in September from $295

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

Return flights

17 Sep - 21 Sep Delta
04 Sep - 07 Sep Delta
03 Sep - 07 Sep Delta
18 Sep - 25 Sep WestJet
27 Sep - 04 Oct WestJet
06 Sep - 13 Sep WestJet
01 Sep - 08 Sep WestJet
02 Sep - 09 Sep WestJet
04 Sep - 11 Sep WestJet
05 Sep - 12 Sep WestJet
07 Sep - 14 Sep WestJet
24 Sep - 01 Oct WestJet
25 Sep - 02 Oct WestJet
26 Sep - 03 Oct WestJet
28 Sep - 05 Oct WestJet
30 Sep - 07 Oct WestJet

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

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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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