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

Return flights

13 Jan - 20 Jan	United	direct
14 Jan - 21 Jan	United	direct
16 Jan - 23 Jan	United	direct
20 Jan - 27 Jan	United	direct
21 Jan - 28 Jan	United	direct
24 Jan - 31 Jan	United	direct
06 Jan - 13 Jan	United
12 Jan - 19 Jan	United
15 Jan - 22 Jan	United
17 Jan - 24 Jan	United
26 Jan - 02 Feb	United	direct
28 Jan - 04 Feb	United	direct
29 Jan - 05 Feb	United	direct
27 Jan - 03 Feb	United
30 Jan - 06 Feb	United
31 Jan - 07 Feb	United
27 Jan - 03 Feb	Air Canada	direct
30 Jan - 06 Feb	Air Canada	direct
31 Jan - 07 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 278€

Return flights