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 $330 round trip and CA $205 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $330 Roundtrip, found 20 hours ago
CA $330
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $330 found 20 hours ago
Thu, Sep 17 - Sun, Sep 20
YYZ
Toronto
ORD
Chicago
CA $360 Roundtrip, found 11 hours ago
CA $360
Roundtrip
found 11 hours ago
Select Delta flight, departing Thu, Sep 17 from Toronto to Chicago, returning Sun, Sep 20, priced at CA $360 found 11 hours ago
Tue, May 26 - Thu, Jun 4
YYZ
Toronto
ORD
Chicago
CA $373 Roundtrip, found 5 days ago
CA $373
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, May 26 from Toronto to Chicago, returning Thu, Jun 4, priced at CA $373 found 5 days ago
Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $383 Roundtrip, found 20 hours ago
CA $383
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $383 found 20 hours ago
Sat, Apr 11 - Tue, Apr 14
YYZ
Toronto
ORD
Chicago
CA $386 Roundtrip, found 2 hours ago
CA $386
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Apr 11 from Toronto to Chicago, returning Tue, Apr 14, priced at CA $386 found 2 hours ago
Sat, May 16 - Mon, Jun 1
YYZ
Toronto
ORD
Chicago
CA $386 Roundtrip, found 2 days ago
CA $386
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, May 16 from Toronto to Chicago, returning Mon, Jun 1, priced at CA $386 found 2 days ago
Wed, Sep 16 - Mon, Sep 21
YYZ
Toronto
ORD
Chicago
CA $388 Roundtrip, found 2 days ago
CA $388
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Sep 16 from Toronto to Chicago, returning Mon, Sep 21, priced at CA $388 found 2 days ago
Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $389 Roundtrip, found 20 hours ago
CA $389
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $389 found 20 hours ago
Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $391 Roundtrip, found 20 hours ago
CA $391
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $391 found 20 hours ago
Sat, Apr 11 - Tue, Apr 14
YYZ
Toronto
ORD
Chicago
CA $394 Roundtrip, found 2 hours ago
CA $394
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Apr 11 from Toronto to Chicago, returning Tue, Apr 14, priced at CA $394 found 2 hours ago

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

Price found within the past 48 hours. Click for updated prices.
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 $975, price is now CA $711 per person
CA $711
per person
Apr 28 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $2,252, price is now CA $1,535 per person
CA $1,535
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Price was CA $1,418, price is now CA $1,097 per person
CA $1,097
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was CA $1,017, price is now CA $797 per person
CA $797
per person
Apr 28 - May 1
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Price was CA $1,269, price is now CA $1,004 per person
CA $1,004
per person
Apr 28 - May 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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.