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

Return flights

06 Jan - 13 Jan	Avianca
07 Jan - 14 Jan	Avianca
12 Jan - 19 Jan	WestJet
13 Jan - 20 Jan	Avianca
14 Jan - 21 Jan	Avianca
21 Jan - 28 Jan	Avianca
22 Jan - 29 Jan	Avianca
26 Jan - 02 Feb	WestJet
27 Jan - 03 Feb	Avianca
28 Jan - 04 Feb	Avianca
29 Jan - 05 Feb	Avianca
06 Jan - 11 Jan	Air Canada	direct
15 Jan - 22 Jan	Avianca
16 Jan - 23 Jan	Avianca
25 Jan - 01 Feb	United	direct
27 Jan - 03 Feb	Air Canada	direct
29 Jan - 05 Feb	Air Canada	direct
30 Jan - 06 Feb	Air Canada	direct
31 Jan - 07 Feb	Air Canada	direct
26 Jan - 02 Feb	Air Canada	direct

Also check the deals for one-way flights from Montreal to Chicago 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 Montreal to Chicago in January from $313

Return flights