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 $235 round trip and CA $165 one way. Prices and availability subject to change. Additional terms may apply.

Sun, Oct. 12 - Tue, Oct. 14
YYZ
Toronto
ORD
Chicago
CA $235 Roundtrip, found 2 days ago
CA $235
Roundtrip
found 2 days ago
Select United flight, departing Sun, Oct. 12 from Toronto to Chicago, returning Tue, Oct. 14, priced at CA $235 found 2 days ago
Sun, Oct. 12 - Tue, Oct. 14
YYZ
Toronto
ORD
Chicago
CA $248 Roundtrip, found 2 days ago
CA $248
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sun, Oct. 12 from Toronto to Chicago, returning Tue, Oct. 14, priced at CA $248 found 2 days ago
Fri, Nov. 14 - Wed, Nov. 19
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, found 4 days ago
CA $261
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov. 14 from Toronto to Chicago, returning Wed, Nov. 19, priced at CA $261 found 4 days ago
Fri, Nov. 14 - Wed, Nov. 19
YYZ
Toronto
ORD
Chicago
CA $265 Roundtrip, found 4 days ago
CA $265
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Nov. 14 from Toronto to Chicago, returning Wed, Nov. 19, priced at CA $265 found 4 days ago
Sat, Dec. 20 - Wed, Dec. 31
YYZ
Toronto
ORD
Chicago
CA $276 Roundtrip, found 2 days ago
CA $276
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Dec. 20 from Toronto to Chicago, returning Wed, Dec. 31, priced at CA $276 found 2 days ago
Sat, Aug. 23 - Sun, Sep. 28
YYZ
Toronto
ORD
Chicago
CA $281 Roundtrip, found 5 days ago
CA $281
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug. 23 from Toronto to Chicago, returning Sun, Sep. 28, priced at CA $281 found 5 days ago
Sun, Oct. 12 - Tue, Oct. 14
YYZ
Toronto
ORD
Chicago
CA $284 Roundtrip, found 2 days ago
CA $284
Roundtrip
found 2 days ago
Select United flight, departing Sun, Oct. 12 from Toronto to Chicago, returning Tue, Oct. 14, priced at CA $284 found 2 days ago
Mon, Nov. 10 - Mon, Dec. 22
YYZ
Toronto
ORD
Chicago
CA $289 Roundtrip, found 4 days ago
CA $289
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Nov. 10 from Toronto to Chicago, returning Mon, Dec. 22, priced at CA $289 found 4 days ago
Fri, Aug. 22 - Sat, Sep. 6
YYZ
Toronto
ORD
Chicago
CA $289 Roundtrip, found 3 days ago
CA $289
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug. 22 from Toronto to Chicago, returning Sat, Sep. 6, priced at CA $289 found 3 days ago
Sun, Oct. 12 - Tue, Oct. 14
YYZ
Toronto
ORD
Chicago
CA $290 Roundtrip, found 2 days ago
CA $290
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Oct. 12 from Toronto to Chicago, returning Tue, Oct. 14, priced at CA $290 found 2 days 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
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip 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.

Popular Flight Routes from Toronto (YYZ)

Travelers at YYZ love to visit these top cities. Roam to the top destinations from Toronto (YYZ) 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.