Cheap flights from Chicago to Montréal
The cheapest round trip from Chicago to Montréal that travelers found recently is $356 with a carry-on: a $356 fare on Air Canada, which usually includes a carry-on. It leaves Fri, Nov 20 and comes back Sun, Nov 22.
Live prices for Fri, Nov 20 to Sun, Nov 22
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Fri, Nov 20 | Sun, Nov 22 | Air Canada | ORD → YUL | 1 stop | $356 | Included | $356 | Live price |
| Thu, Dec 24 | Mon, Dec 28 | United | ORD → YUL | 1 stop | $404 | Included | $404 | Live price |
| Fri, Oct 30 | Tue, Nov 3 | American Airlines | ORD → YUL | Nonstop | $439 | Included | $439 | Live price |
| Fri, Nov 20 | Sun, Nov 29 | Air Canada | ORD → YUL | 1 stop | $490 | Included | $490 | Live price |
| Sat, Nov 21 | Sun, Nov 29 | Air Canada | ORD → YUL | 1 stop | $490 | Included | $490 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Fri, Oct 30 to Tue, Nov 3, 4 nights | $439 | Live price |
| November 2026 | Fri, Nov 20 to Sun, Nov 22, 2 nights | $356 | Live price |
| December 2026 | Thu, Dec 24 to Mon, Dec 28, 4 nights | $404 | Live price |
Bag fees on this route
What the airlines flying Chicago to Montréal usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| Air Canada | Included | $40 |
| American Airlines | Included | $40 |
| United | Included | $40 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
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