Cheap Flights from Montreal (YUL) to Chicago (ORD)

View AU$185 flight on Wed, 28 Jan 2026Opens in a new window

Popular airlines from Trudeau International Airport (YUL) to Chicago O'Hare International Airport (ORD)

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Cheap Flights from Montreal (YUL) to Chicago (ORD)

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

Air Canada
Tue, 10 Feb - Sat, 14 Feb
YUL
Montreal
ORD
Chicago
AU$288 Return, found 4 days ago
AU$288
Return
found 4 days ago
Select Air Canada flight, departing Tue, 10 Feb from Montreal to Chicago, returning Sat, 14 Feb, priced at AU$288 found 4 days ago
United
Wed, 3 June - Sat, 6 June
YUL
Montreal
ORD
Chicago
AU$288 Return, found 1 hour ago
AU$288
Return
found 1 hour ago
Select United flight, departing Wed, 3 June from Montreal to Chicago, returning Sat, 6 June, priced at AU$288 found 1 hour ago
United
Wed, 3 June - Sat, 6 June
YUL
Montreal
ORD
Chicago
AU$297 Return, found 1 hour ago
AU$297
Return
found 1 hour ago
Select United flight, departing Wed, 3 June from Montreal to Chicago, returning Sat, 6 June, priced at AU$297 found 1 hour ago
Air Canada
Tue, 10 Feb - Sat, 14 Feb
YUL
Montreal
ORD
Chicago
AU$327 Return, found 4 days ago
AU$327
Return
found 4 days ago
Select Air Canada flight, departing Tue, 10 Feb from Montreal to Chicago, returning Sat, 14 Feb, priced at AU$327 found 4 days ago
Delta
Tue, 10 Feb - Sat, 14 Feb
YUL
Montreal
ORD
Chicago
AU$329 Return, found 4 days ago
AU$329
Return
found 4 days ago
Select Delta flight, departing Tue, 10 Feb from Montreal to Chicago, returning Sat, 14 Feb, priced at AU$329 found 4 days ago
Delta
Tue, 10 Feb - Sat, 14 Feb
YUL
Montreal
ORD
Chicago
AU$330 Return, found 4 days ago
AU$330
Return
found 4 days ago
Select Delta flight, departing Tue, 10 Feb from Montreal to Chicago, returning Sat, 14 Feb, priced at AU$330 found 4 days ago
United
Fri, 5 June - Sun, 7 June
YUL
Montreal
ORD
Chicago
AU$345 Return, just found
AU$345
Return
just found
Select United flight, departing Fri, 5 June from Montreal to Chicago, returning Sun, 7 June, priced at AU$345 just found
United
Fri, 5 June - Sun, 7 June
YUL
Montreal
ORD
Chicago
AU$354 Return, just found
AU$354
Return
just found
Select United flight, departing Fri, 5 June from Montreal to Chicago, returning Sun, 7 June, priced at AU$354 just found
American Airlines
Tue, 10 Feb - Sat, 14 Feb
YUL
Montreal
ORD
Chicago
AU$384 Return, found 4 days ago
AU$384
Return
found 4 days ago
Select American Airlines flight, departing Tue, 10 Feb from Montreal to Chicago, returning Sat, 14 Feb, priced at AU$384 found 4 days ago
WestJet
Wed, 31 Dec - Sat, 25 July
YUL
Montreal
ORD
Chicago
AU$573 Return, found 3 days ago
AU$573
Return
found 3 days ago
Select WestJet flight, departing Wed, 31 Dec from Montreal to Chicago, returning Sat, 25 July, priced at AU$573 found 3 days ago

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

September is typically the cheapest month to fly

From AU$247 - AU$455 per traveller.

Frequently asked questions

How much is a flight from Pierre Elliott Trudeau Intl. Airport (YUL) to O'Hare Airport?
If you're planning on travelling between Montréal–Trudeau and ORD, round-trip flights start from AU$288. This figure is based on airfares listed within the last 7 days on Expedia for flights departing within the next year, so don't delay. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Pierre Elliott Trudeau Intl. Airport (YUL) to ORD?
We understand that your situation can change unexpectedly, so we've made it as easy as possible for you to cancel your flight online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from Pierre Elliott Trudeau Intl. Airport (YUL) to ORD 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 YUL to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Montréal–Trudeau to ORD?
The flight distance from Pierre Elliott Trudeau Intl. Airport (YUL) (YUL) to O'Hare Airport (ORD) is 1 200 kilometres. You'll be disembarking the plane and collecting your baggage from the carousel in no time at all.
Which airlines fly direct from Montréal–Trudeau to O'Hare Airport?
There are several airlines that travel directly from Montréal–Trudeau to O'Hare Intl. Airport (ORD). Air Canada (AC) is an excellent choice, offering 91 flights a month. Offering 30 flights a month on this route, United Airlines (UA) is another good option.
Are Montréal–Trudeau to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Booking last minute from YUL to ORD can be hit-or-miss. You may be able to score a bargain, but you could also completely miss out! If you'd rather start your travel planning early on, Expedia compares flight deals up to a year in advance. Just keep in mind that not all airlines release their prices so far in advance. Our suggestion? Check back often as prices are updated regularly.

Travel information

Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
O'Hare Intl.
Return price
AU$287
Distance
1192 km
Average flight time
1 hour 36 mins

Book with confidence

Your quick guide to flights from Montreal to Chicago

Pick up great flights from Montreal to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Montreal to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Montreal to Chicago that take around hours.

Find cheap flights from Montreal to Chicago

From the great flight deals with prices currently ranging from AU$288 to AU$573, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Montreal to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in February.

Reasons to book your flight from Montreal to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Montreal to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Your quick guide to flights from Montreal to Chicago

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