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Cheap flights from Montreal (YUL) to Chicago (MDW)

YUL Montreal
MDW Chicago
200
Flights
$446
Lowest
$834
Average
Oct 12, 2026 - Mar 27, 2027
Date Range
15% above typical Check live prices Alert me on this route

Round-trip Montreal to Chicago currently starts at $446 CAD with taxes included, averaging $834 across 200 tracked fares departing Oct 12, 2026 to Mar 27, 2027.

YUL to MDW price history

Cheapest right now $446
Typical low $388
51-day range $338 to $445

15% above the typical low ($388), so this is a poor time to buy.

Aug 30, 2026 Typical low $388 Sep 29, 2026

↑ Trending up: 9.6% above the last 30-day average.

· FareSeeker tracking data: 200 fares monitored on this route by our own collector, refreshed several times daily.

The 5 cheapest fares right now

Dates Trip Airline Stops Price
Oct 17, 2026 → Oct 21, 2026 4 nights PD Porter Airlines 2 $446 CAD
Oct 16, 2026 → Oct 21, 2026 5 nights PD Porter Airlines 2 $476 CAD
Oct 19, 2026 → Oct 23, 2026 4 nights PD Porter Airlines 2 $496 CAD
Oct 19, 2026 → Oct 24, 2026 5 nights PD Porter Airlines 2 $496 CAD
Oct 20, 2026 → Oct 24, 2026 4 nights PD Porter Airlines 2 $496 CAD

All fares are round trip. Exact flight times show on the booking page.

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