CA $188 Cheap Flights from Montreal (YUL) to Chicago (MDW)

View CA $188 flight on Thu, Jun 4, 2026Opens in a new window

Popular airlines from Trudeau International Airport (YUL) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at CA $188 for one-way flights and CA $302 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Jun 4 - Sun, Jun 7
YUL
Montreal
MDW
Chicago
CA $302 Roundtrip, found 1 hour ago
CA $302
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu, Jun 4 from Montreal to Chicago, returning Sun, Jun 7, priced at CA $302 found 1 hour ago
Porter Airlines
Thu, Jun 4 - Sun, Jun 7
YUL
Montreal
MDW
Chicago
CA $352 Roundtrip, found 1 hour ago
CA $352
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu, Jun 4 from Montreal to Chicago, returning Sun, Jun 7, priced at CA $352 found 1 hour ago
Porter Airlines
Wed, May 20 - Wed, Jun 3
YUL
Montreal
MDW
Chicago
CA $377 Roundtrip, found 2 days ago
CA $377
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Wed, May 20 from Montreal to Chicago, returning Wed, Jun 3, priced at CA $377 found 2 days ago
Porter Airlines
Wed, May 20 - Fri, Jun 5
YUL
Montreal
MDW
Chicago
CA $378 Roundtrip, found 6 days ago
CA $378
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Wed, May 20 from Montreal to Chicago, returning Fri, Jun 5, priced at CA $378 found 6 days ago
Delta
Tue, May 19 - Tue, Jun 2
YUL
Montreal
MDW
Chicago
CA $382 Roundtrip, found 2 days ago
CA $382
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, May 19 from Montreal to Chicago, returning Tue, Jun 2, priced at CA $382 found 2 days ago
Porter Airlines
Thu, Jun 4 - Sun, Jun 7
YUL
Montreal
MDW
Chicago
CA $386 Roundtrip, found 1 hour ago
CA $386
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu, Jun 4 from Montreal to Chicago, returning Sun, Jun 7, priced at CA $386 found 1 hour ago
Porter Airlines
Thu, Jun 4 - Sun, Jun 7
YUL
Montreal
MDW
Chicago
CA $387 Roundtrip, found 1 hour ago
CA $387
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu, Jun 4 from Montreal to Chicago, returning Sun, Jun 7, priced at CA $387 found 1 hour ago
Porter Airlines
Mon, Jun 8 - Mon, Jun 22
YUL
Montreal
MDW
Chicago
CA $390 Roundtrip, found 2 days ago
CA $390
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Mon, Jun 8 from Montreal to Chicago, returning Mon, Jun 22, priced at CA $390 found 2 days ago
Porter Airlines
Fri, May 29 - Mon, Jun 1
YUL
Montreal
MDW
Chicago
CA $392 Roundtrip, found 2 hours ago
CA $392
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Fri, May 29 from Montreal to Chicago, returning Mon, Jun 1, priced at CA $392 found 2 hours ago
Porter Airlines
Thu, Jun 4 - Fri, Jun 5
YUL
Montreal
MDW
Chicago
CA $399 Roundtrip, found 2 days ago
CA $399
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Thu, Jun 4 from Montreal to Chicago, returning Fri, Jun 5, priced at CA $399 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $420
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $420

Frequently asked questions

How much is a flight from Montréal–Trudeau to Chicago Airport?
Start packing your bags, because round-trip journeys between YUL and MDW start from CA $302. That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can rise quickly, so book today to secure the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from YUL to Midway Intl. Airport (MDW)?
The majority of flights can be cancelled online, but each airline has its own set of terms and conditions. If you do decide to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from YUL to Midway Airport that have flexible change policies?
Flights from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Airport offering flexible change policies are available from several carriers. Simply use our "No change fees" filter during your search. You'll only need to pay the difference in ticket price, with no added fees to worry about.
How many hours is the flight from Pierre Elliott Trudeau Intl. Airport (YUL) to MDW?
It takes around 4 hours and 17 minutes to fly from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago Airport. But with some movies and a good book, the hours will pass by quicker.
How far is the flight from Pierre Elliott Trudeau Intl. Airport (YUL) to MDW?
A flight distance of just 1,200 kilometres separates Dorval and Chicago. Once you're in the air, you won't have time to do much more than read the magazine in your seat pocket.
Which airlines fly direct from YUL to Chicago Airport?
Right now, no airlines offer flights directly from Montreal Airport to Chicago Airport. You'll need to book a flight with one or more stops. To score the best price and connections, lock in your fare well in advance.
Are Montréal–Trudeau to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Flight tickets from Montreal Airport to Midway Airport are available up to a year before departure on Expedia. And although you may nab great last-minute deal, it's not something you should count on. Also, booking your flights in advance means you'll have more options — and you can avoid landing the dreaded middle seat! We're constantly updating our fares to bring you the best bargains, so check back often for all the latest specials.

Travel information

Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
CA $302
Distance
1188 km

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