CA $197 Cheap Flights from Montreal (YUL) to Chicago (MDW)

View CA $197 flight on Thu, May 22, 2025Opens 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 $197 for one-way flights and CA $321 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu., May 22 - Thu., May 29
YUL
Montreal
MDW
Chicago
CA $321 Roundtrip, found 1 hour ago
CA $321
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu., May 22 from Montreal to Chicago, returning Thu., May 29, priced at CA $321 found 1 hour ago
Delta
Thu., May 22 - Thu., May 29
YUL
Montreal
MDW
Chicago
CA $328 Roundtrip, found 1 hour ago
CA $328
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu., May 22 from Montreal to Chicago, returning Thu., May 29, priced at CA $328 found 1 hour ago
Delta
Wed., Oct. 1 - Sat., Oct. 11
YUL
Montreal
MDW
Chicago
CA $335 Roundtrip, found 21 hours ago
CA $335
Roundtrip
found 21 hours ago
Select Delta flight, departing Wed., Oct. 1 from Montreal to Chicago, returning Sat., Oct. 11, priced at CA $335 found 21 hours ago
Porter Airlines
Thu., May 22 - Thu., May 29
YUL
Montreal
MDW
Chicago
CA $347 Roundtrip, found 1 hour ago
CA $347
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu., May 22 from Montreal to Chicago, returning Thu., May 29, priced at CA $347 found 1 hour ago
Porter Airlines
Sun., May 11 - Sun., May 18
YUL
Montreal
MDW
Chicago
CA $347 Roundtrip, found 23 hours ago
CA $347
Roundtrip
found 23 hours ago
Select Porter Airlines flight, departing Sun., May 11 from Montreal to Chicago, returning Sun., May 18, priced at CA $347 found 23 hours ago
Porter Airlines
Wed., Jun. 18 - Wed., Jul. 9
YUL
Montreal
MDW
Chicago
CA $348 Roundtrip, found 21 hours ago
CA $348
Roundtrip
found 21 hours ago
Select Porter Airlines flight, departing Wed., Jun. 18 from Montreal to Chicago, returning Wed., Jul. 9, priced at CA $348 found 21 hours ago
Delta
Thu., Sep. 18 - Tue., Sep. 23
YUL
Montreal
MDW
Chicago
CA $351 Roundtrip, found 6 hours ago
CA $351
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu., Sep. 18 from Montreal to Chicago, returning Tue., Sep. 23, priced at CA $351 found 6 hours ago
Delta
Thu., May 22 - Thu., May 29
YUL
Montreal
MDW
Chicago
CA $354 Roundtrip, found 1 hour ago
CA $354
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu., May 22 from Montreal to Chicago, returning Thu., May 29, priced at CA $354 found 1 hour ago
Delta
Mon., Jul. 7 - Sat., Jul. 12
YUL
Montreal
MDW
Chicago
CA $355 Roundtrip, found 1 day ago
CA $355
Roundtrip
found 1 day ago
Select Delta flight, departing Mon., Jul. 7 from Montreal to Chicago, returning Sat., Jul. 12, priced at CA $355 found 1 day ago
WestJet
Sun., May 25 - Wed., Jun. 4
YUL
Montreal
MDW
Chicago
CA $463 Roundtrip, found 20 hours ago
CA $463
Roundtrip
found 20 hours ago
Select WestJet flight, departing Sun., May 25 from Montreal to Chicago, returning Wed., Jun. 4, priced at CA $463 found 20 hours ago
Flight from Montreal to Chicago (YUL - MDW) route information
Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
CA $320
Distance
1188 km

Montreal to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Montreal to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from YUL to MDW and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Montreal to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from YUL to MDW. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

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 CA $321. 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 canceled 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 kilometers. 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.

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