Cheap Flights From Pierre Elliott Trudeau Intl. (YUL) To O'Hare Intl. (ORD)

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

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $392 round trip and CA $233 one way. Prices and availability subject to change. Additional terms may apply.

Sun, Nov 23 - Sat, Nov 29
YUL
Montreal
ORD
Chicago
CA $392 Roundtrip, found 4 days ago
CA $392
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sun, Nov 23 from Montreal to Chicago, returning Sat, Nov 29, priced at CA $392 found 4 days ago
Tue, Oct 28 - Tue, Oct 28
YUL
Montreal
ORD
Chicago
CA $392 Roundtrip, found 2 days ago
CA $392
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 28 from Montreal to Chicago, returning Tue, Oct 28, priced at CA $392 found 2 days ago
Fri, Nov 21 - Sat, Nov 29
YUL
Montreal
ORD
Chicago
CA $394 Roundtrip, found 4 days ago
CA $394
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Nov 21 from Montreal to Chicago, returning Sat, Nov 29, priced at CA $394 found 4 days ago
Wed, Oct 1 - Sat, Oct 4
YUL
Montreal
ORD
Chicago
CA $400 Roundtrip, found 4 days ago
CA $400
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Oct 1 from Montreal to Chicago, returning Sat, Oct 4, priced at CA $400 found 4 days ago
Wed, Oct 15 - Wed, Oct 22
YUL
Montreal
ORD
Chicago
CA $400 Roundtrip, found 16 hours ago
CA $400
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Oct 15 from Montreal to Chicago, returning Wed, Oct 22, priced at CA $400 found 16 hours ago
Sat, Nov 22 - Tue, Dec 9
YUL
Montreal
ORD
Chicago
CA $401 Roundtrip, found 5 days ago
CA $401
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Nov 22 from Montreal to Chicago, returning Tue, Dec 9, priced at CA $401 found 5 days ago
Fri, Nov 21 - Sun, Nov 23
YUL
Montreal
ORD
Chicago
CA $402 Roundtrip, found 4 hours ago
CA $402
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Nov 21 from Montreal to Chicago, returning Sun, Nov 23, priced at CA $402 found 4 hours ago
Sat, Oct 11 - Wed, Oct 22
YUL
Montreal
ORD
Chicago
CA $411 Roundtrip, found 1 day ago
CA $411
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Oct 11 from Montreal to Chicago, returning Wed, Oct 22, priced at CA $411 found 1 day ago
Wed, Oct 1 - Thu, Oct 9
YUL
Montreal
ORD
Chicago
CA $412 Roundtrip, found 5 days ago
CA $412
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Oct 1 from Montreal to Chicago, returning Thu, Oct 9, priced at CA $412 found 5 days ago
Sat, Oct 11 - Wed, Oct 22
YUL
Montreal
ORD
Chicago
CA $414 Roundtrip, found 1 day ago
CA $414
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Oct 11 from Montreal to Chicago, returning Wed, Oct 22, priced at CA $414 found 1 day ago

O'Hare Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
Price was CA $1,102, price is now CA $742 per person
CA $742
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was CA $1,414, price is now CA $862 per person
CA $862
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was CA $2,011, price is now CA $1,259 per person
CA $1,259
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was CA $1,561, price is now CA $1,048 per person
CA $1,048
per person
Oct 22 - Oct 26
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was CA $1,176, price is now CA $792 per person
CA $792
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
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Frequently asked questions

Are there direct flights from YUL to O'Hare Intl. Airport (ORD)?
Multiple airlines advertise flights straight from YUL to O'Hare Airport. Among these are Air Canada and United Airlines — start with them if you'd like to touch down at Chicago with minimal fuss.
What airlines fly from YUL to O'Hare Intl. Airport (ORD)?
You can take your pick from a few airlines that advertise direct flights between Montreal and Chicago. Air Canada (AC) is one of the most popular. This air carrier operates around 91 flights each month. Don't forget to also browse the deals available through United Airlines (UA). This airline operates 30 flights every month on the Montreal to Chicago route. Be sure to compare the two airlines to find your ideal fare.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Montreal (YUL)

Travelers at YUL love to visit these top cities. Roam to the top destinations from Montreal (YUL) today with the cheap prices from Travelocity!

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago(ORD) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.