Cheapest return flights from Montreal to Chicago in January from $272

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

Return flights

03 Jan - 10 Jan Air Canada direct
06 Jan - 13 Jan Air Canada direct
07 Jan - 14 Jan Air Canada direct
08 Jan - 15 Jan Air Canada direct
09 Jan - 16 Jan Air Canada direct
10 Jan - 17 Jan Air Canada direct
13 Jan - 20 Jan Air Canada direct
14 Jan - 21 Jan Air Canada direct
15 Jan - 22 Jan Air Canada direct
16 Jan - 23 Jan Air Canada direct
26 Jan - 02 Feb Air Canada direct
27 Jan - 03 Feb Air Canada direct
28 Jan - 04 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
25 Jan - 01 Feb Air Canada direct

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

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.