S$219 Cheap Flights from Montreal to Chicago

View S$219 flight on Mon, 24 Nov, 2025Opens in a new window

Popular airlines from Montreal–Trudeau Intl. Airport (YUL) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Montreal to Chicago (YUL-ORD)

Prices were available within the past 7 days and start at S$219 for one-way flights and S$376 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$376 Return, found 1 day ago
S$376
Return
found 1 day ago
Select United flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$376 found 1 day ago
United
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$383 Return, found 1 day ago
S$383
Return
found 1 day ago
Select United flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$383 found 1 day ago
United
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$384 Return, found 1 day ago
S$384
Return
found 1 day ago
Select United flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$384 found 1 day ago
Air Canada
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$386 Return, found 1 day ago
S$386
Return
found 1 day ago
Select Air Canada flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$386 found 1 day ago
Air Canada
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$395 Return, found 1 day ago
S$395
Return
found 1 day ago
Select Air Canada flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$395 found 1 day ago
Air Canada
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$395 Return, found 1 day ago
S$395
Return
found 1 day ago
Select Air Canada flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$395 found 1 day ago
Delta
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$400 Return, found 1 day ago
S$400
Return
found 1 day ago
Select Delta flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$400 found 1 day ago
United
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$402 Return, found 1 day ago
S$402
Return
found 1 day ago
Select United flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$402 found 1 day ago
Air Canada
Mon, 24 Nov - Mon, 1 Dec
YUL
Montreal
ORD
Chicago
S$403 Return, found 1 day ago
S$403
Return
found 1 day ago
Select Air Canada flight, departing Mon, 24 Nov from Montreal to Chicago, returning Mon, 1 Dec, priced at S$403 found 1 day ago
American Airlines
Sun, 1 Mar - Fri, 6 Mar
YUL
Montreal
ORD
Chicago
S$522 Return, found 1 day ago
S$522
Return
found 1 day ago
Select American Airlines flight, departing Sun, 1 Mar from Montreal to Chicago, returning Fri, 6 Mar, priced at S$522 found 1 day ago

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

September is typically the cheapest month to fly

From S$211 - S$389 per traveller.
Montreal to Chicago route information
Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United
Return price
S$376
Distance
1192 km
Average flight time
1 hour 36 mins

Flights from Montreal to Chicago

There are several airlines that operate frequent flights from Montreal (YUL) to Chicago (ORD) including

The earliest flight leaves Pierre Elliott Trudeau Intl. Airport at 06:20 and arrives at O'Hare Intl. Airport at 07:55. The last flight of the day departs Montreal at 20:00 and arrives at Chicago at 21:25.

The flight distance from Montreal to Chicago is about 1207 km, the shortest flight is 02 hours 21 minutes with WestJet.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Montreal Chicago flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Montreal to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

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 Montreal to Chicago with Expedia. Use us as your stop 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 O'Hare Airport?
If you're planning on travelling between Montréal–Trudeau and ORD, round-trip flights start from S$376. 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.

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