Cheap Flights From Pearson Intl. (YYZ) To O'Hare Intl. (ORD)

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Cheapest Flights from Toronto (YYZ) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $345 round trip and CA $219 one way. Prices and availability subject to change. Additional terms may apply.

Mon, Jun 1 - Tue, Jun 2
YYZ
Toronto
ORD
Chicago
CA $345 Roundtrip, found 5 days ago
CA $345
Roundtrip
found 5 days ago
Select Air Canada flight, departing Mon, Jun 1 from Toronto to Chicago, returning Tue, Jun 2, priced at CA $345 found 5 days ago
Sun, May 24 - Sat, May 30
YYZ
Toronto
ORD
Chicago
CA $345 Roundtrip, found 4 days ago
CA $345
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, May 24 from Toronto to Chicago, returning Sat, May 30, priced at CA $345 found 4 days ago
Fri, Apr 24 - Sat, Apr 25
YYZ
Toronto
ORD
Chicago
CA $351 Roundtrip, found 3 days ago
CA $351
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Apr 24 from Toronto to Chicago, returning Sat, Apr 25, priced at CA $351 found 3 days ago
Sun, May 31 - Sun, Jun 7
YYZ
Toronto
ORD
Chicago
CA $351 Roundtrip, found 5 days ago
CA $351
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, May 31 from Toronto to Chicago, returning Sun, Jun 7, priced at CA $351 found 5 days ago
Wed, Jun 3 - Tue, Jun 9
YYZ
Toronto
ORD
Chicago
CA $365 Roundtrip, found 1 day ago
CA $365
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jun 3 from Toronto to Chicago, returning Tue, Jun 9, priced at CA $365 found 1 day ago
Wed, Jun 3 - Tue, Jun 9
YYZ
Toronto
ORD
Chicago
CA $373 Roundtrip, found 1 day ago
CA $373
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jun 3 from Toronto to Chicago, returning Tue, Jun 9, priced at CA $373 found 1 day ago
Tue, Jun 9 - Tue, Jun 16
YYZ
Toronto
ORD
Chicago
CA $381 Roundtrip, found 4 days ago
CA $381
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jun 9 from Toronto to Chicago, returning Tue, Jun 16, priced at CA $381 found 4 days ago
Tue, Jun 2 - Fri, Jun 5
YYZ
Toronto
ORD
Chicago
CA $382 Roundtrip, found 5 days ago
CA $382
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 2 from Toronto to Chicago, returning Fri, Jun 5, priced at CA $382 found 5 days ago
Tue, Jun 9 - Tue, Jun 16
YYZ
Toronto
ORD
Chicago
CA $388 Roundtrip, found 4 days ago
CA $388
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jun 9 from Toronto to Chicago, returning Tue, Jun 16, priced at CA $388 found 4 days ago
Sat, May 2 - Sun, May 3
YYZ
Toronto
ORD
Chicago
CA $393 Roundtrip, found 3 hours ago
CA $393
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, May 2 from Toronto to Chicago, returning Sun, May 3, priced at CA $393 found 3 hours ago

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

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Price was CA $1,064, price is now CA $827 per person
CA $827
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was CA $1,319, price is now CA $879 per person
CA $879
per person
Apr 16 - Apr 19
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was CA $1,890, price is now CA $1,310 per person
CA $1,310
per person
May 6 - May 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Price was CA $1,886, price is now CA $1,323 per person
CA $1,323
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $1,330, price is now CA $958 per person
CA $958
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
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Frequently asked questions

Are there direct flights from Pearson Intl. Airport (YYZ) to ORD?
If you're hoping to venture from Toronto Pearson Airport to O'Hare Airport as quickly as possible, you'll be glad to know multiple airlines operate direct flights. Pick your favorite seat with Air Canada or United Airlines.
What airlines fly from YYZ to O'Hare Intl. Airport (ORD)?
If you're flying to Chicago from Toronto, there are several airlines that offer direct flights. One of the leading carriers is Air Canada (AC), which has 152 flights every month. Another popular choice is United Airlines (UA), which offers 91 flights each month. The more airlines you consider, the more likely you are to find an amazing deal.
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.

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*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.