RM585 Cheap Flights from Montreal (YUL) to Chicago (MDW)

View RM585 flight on Fri, 8 May 2026Opens in a new window

Flight 1

Popular airlines from Montreal–Trudeau Intl. Airport (YUL) to Chicago Midway Airport (MDW)

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Cheap Flights from Montreal to Chicago (YUL-MDW)

Prices were available within the past 7 days and start at RM585 for one-way flights and RM999 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM999 Return, found 6 days ago
RM999
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM999 found 6 days ago
Delta
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,065 Return, found 6 days ago
RM1,065
Return
found 6 days ago
Select Delta flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,065 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,094 Return, found 6 days ago
RM1,094
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,094 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,119 Return, found 6 days ago
RM1,119
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,119 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,156 Return, found 6 days ago
RM1,156
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,156 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,176 Return, found 6 days ago
RM1,176
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,176 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,214 Return, found 6 days ago
RM1,214
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,214 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,251 Return, found 6 days ago
RM1,251
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,251 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,271 Return, found 6 days ago
RM1,271
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,271 found 6 days ago
Porter Airlines
Fri, 8 May - Fri, 15 May
YUL
Montreal
MDW
Chicago
RM1,276 Return, found 6 days ago
RM1,276
Return
found 6 days ago
Select Porter Airlines flight, departing Fri, 8 May from Montreal to Chicago, returning Fri, 15 May, priced at RM1,276 found 6 days ago

Find the cheapest month to fly from Montreal (YUL) to Chicago (MDW)

January is typically the cheapest month to fly

From RM 621 - RM 1,952 per traveller.

Frequently asked questions

How much is a flight from Pierre Elliott Trudeau Intl. Airport (YUL) to MDW?
Round-trip tickets between Pierre Elliott Trudeau Intl. Airport (YUL) and Chicago Airport start from RM999. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Montréal–Trudeau to Midway Intl. Airport (MDW)?
Most flights can be cancelled online, but each air carrier has its own set of terms and conditions. If you do have to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Montréal–Trudeau to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Airport?
The flight distance from Montreal Airport (YUL) to Chicago Airport (MDW) is 1,200 kilometres. You'll be stepping off the plane and collecting your suitcase from the carousel in the blink of an eye.
Which airlines fly direct from Montreal Airport to Midway Intl. Airport (MDW)?
Flying directly between Montréal–Trudeau and Chicago Airport isn't possible at present. However, you'll still be able to book a flight to Chicago with at least one stop.
Are Montréal–Trudeau to Chicago Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW) at the last minute could save you some cash. However, it could end up costing a great deal more! If you'd prefer not to take the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back regularly as deals are updated all the time on Expedia.

Travel information

Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
Midway Intl.
Return price
RM999
Distance
1188 km

Book with confidence

Perfect flights from Montreal to Chicago

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Montreal to Chicago

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