CA $229 Cheap Flights from Montreal (YUL) to Chicago (ORD)

View CA $229 flight on Sun, Jun. 15, 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at CA $229 for one-way flights and CA $384 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat., May 3 - Sat., May 17
YUL
Montreal
ORD
Chicago
CA $384 Roundtrip, found 3 days ago
CA $384
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat., May 3 from Montreal to Chicago, returning Sat., May 17, priced at CA $384 found 3 days ago
Air Canada
Thu., May 29 - Tue., Jun. 3
YUL
Montreal
ORD
Chicago
CA $384 Roundtrip, found 4 hours ago
CA $384
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Thu., May 29 from Montreal to Chicago, returning Tue., Jun. 3, priced at CA $384 found 4 hours ago
United
Tue., May 6 - Tue., May 27
YUL
Montreal
ORD
Chicago
CA $384 Roundtrip, found 6 hours ago
CA $384
Roundtrip
found 6 hours ago
Select United flight, departing Tue., May 6 from Montreal to Chicago, returning Tue., May 27, priced at CA $384 found 6 hours ago
American Airlines
Sat., May 31 - Sun., Jun. 1
YUL
Montreal
ORD
Chicago
CA $392 Roundtrip, found 4 hours ago
CA $392
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat., May 31 from Montreal to Chicago, returning Sun., Jun. 1, priced at CA $392 found 4 hours ago
United
Thu., May 1 - Mon., May 12
YUL
Montreal
ORD
Chicago
CA $393 Roundtrip, found 3 days ago
CA $393
Roundtrip
found 3 days ago
Select United flight, departing Thu., May 1 from Montreal to Chicago, returning Mon., May 12, priced at CA $393 found 3 days ago
Air Canada
Fri., May 9 - Sun., May 11
YUL
Montreal
ORD
Chicago
CA $401 Roundtrip, just found
CA $401
Roundtrip
just found
Select Air Canada flight, departing Fri., May 9 from Montreal to Chicago, returning Sun., May 11, priced at CA $401 just found
Air Canada
Sun., Jun. 1 - Tue., Jun. 17
YUL
Montreal
ORD
Chicago
CA $402 Roundtrip, found 1 hour ago
CA $402
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sun., Jun. 1 from Montreal to Chicago, returning Tue., Jun. 17, priced at CA $402 found 1 hour ago
Air Canada
Mon., Jun. 2 - Wed., Jun. 18
YUL
Montreal
ORD
Chicago
CA $404 Roundtrip, found 23 hours ago
CA $404
Roundtrip
found 23 hours ago
Select Air Canada flight, departing Mon., Jun. 2 from Montreal to Chicago, returning Wed., Jun. 18, priced at CA $404 found 23 hours ago
American Airlines
Wed., May 7 - Thu., May 15
YUL
Montreal
ORD
Chicago
CA $407 Roundtrip, found 6 hours ago
CA $407
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed., May 7 from Montreal to Chicago, returning Thu., May 15, priced at CA $407 found 6 hours ago
Delta
Wed., May 7 - Fri., May 16
YUL
Montreal
ORD
Chicago
CA $415 Roundtrip, found 6 hours ago
CA $415
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed., May 7 from Montreal to Chicago, returning Fri., May 16, priced at CA $415 found 6 hours ago
Flight from Montreal to Chicago (YUL - ORD) route information
Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Delta, United, WestJet
Roundtrip price
CA $384
Distance
1192 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 ORD 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 ORD. 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 O'Hare Airport?
If you’re planning on traveling between Montréal–Trudeau and ORD, round-trip flights start from CA $384. 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 kilometers. 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.

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

Montreal to Midway Intl.
CA $383.52
Montreal nearby Airports

Montreal Metropolitan Airport

*Available to Expedia members.