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 $270 round trip and CA $177 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Oct. 24 - Sat, Nov. 1
YUL
Montreal
ORD
Chicago
CA $270 Roundtrip, found 19 hours ago
CA $270
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Fri, Oct. 24 from Montreal to Chicago, returning Sat, Nov. 1, priced at CA $270 found 19 hours ago
Mon, Sep. 8 - Thu, Sep. 11
YUL
Montreal
ORD
Chicago
CA $272 Roundtrip, found 5 days ago
CA $272
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Sep. 8 from Montreal to Chicago, returning Thu, Sep. 11, priced at CA $272 found 5 days ago
Wed, Aug. 27 - Tue, Sep. 2
YUL
Montreal
ORD
Chicago
CA $272 Roundtrip, found 4 days ago
CA $272
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Aug. 27 from Montreal to Chicago, returning Tue, Sep. 2, priced at CA $272 found 4 days ago
Sat, Sep. 13 - Sun, Sep. 14
YUL
Montreal
ORD
Chicago
CA $280 Roundtrip, found 1 hour ago
CA $280
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sat, Sep. 13 from Montreal to Chicago, returning Sun, Sep. 14, priced at CA $280 found 1 hour ago
Thu, Sep. 4 - Sat, Sep. 13
YUL
Montreal
ORD
Chicago
CA $296 Roundtrip, found 1 day ago
CA $296
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep. 4 from Montreal to Chicago, returning Sat, Sep. 13, priced at CA $296 found 1 day ago
Sun, Oct. 26 - Wed, Oct. 29
YUL
Montreal
ORD
Chicago
CA $306 Roundtrip, found 19 hours ago
CA $306
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Sun, Oct. 26 from Montreal to Chicago, returning Wed, Oct. 29, priced at CA $306 found 19 hours ago
Sat, Aug. 23 - Sun, Aug. 24
YUL
Montreal
ORD
Chicago
CA $317 Roundtrip, found 6 days ago
CA $317
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Aug. 23 from Montreal to Chicago, returning Sun, Aug. 24, priced at CA $317 found 6 days ago
Sat, Aug. 23 - Sun, Aug. 24
YUL
Montreal
ORD
Chicago
CA $324 Roundtrip, found 6 days ago
CA $324
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Aug. 23 from Montreal to Chicago, returning Sun, Aug. 24, priced at CA $324 found 6 days ago
Sun, Oct. 26 - Wed, Oct. 29
YUL
Montreal
ORD
Chicago
CA $345 Roundtrip, found 19 hours ago
CA $345
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Sun, Oct. 26 from Montreal to Chicago, returning Wed, Oct. 29, priced at CA $345 found 19 hours ago
Sat, Sep. 13 - Sat, Sep. 13
YUL
Montreal
ORD
Chicago
CA $345 Roundtrip, found 1 hour ago
CA $345
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sat, Sep. 13 from Montreal to Chicago, returning Sat, Sep. 13, priced at CA $345 found 1 hour ago

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

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip 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.