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 $257 round trip and CA $186 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 14 - Sat, Jan 17
YYZ
Toronto
ORD
Chicago
CA $257 Roundtrip, found 2 days ago
CA $257
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed, Jan 14 from Toronto to Chicago, returning Sat, Jan 17, priced at CA $257 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
YYZ
Toronto
ORD
Chicago
CA $257 Roundtrip, found 2 days ago
CA $257
Roundtrip
found 2 days ago
Select United flight, departing Sat, Jan 17 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $257 found 2 days ago
Sat, Jan 17 - Sun, Feb 15
YYZ
Toronto
ORD
Chicago
CA $263 Roundtrip, found 3 days ago
CA $263
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jan 17 from Toronto to Chicago, returning Sun, Feb 15, priced at CA $263 found 3 days ago
Thu, Jan 15 - Sun, Feb 15
YYZ
Toronto
ORD
Chicago
CA $271 Roundtrip, found 2 days ago
CA $271
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Jan 15 from Toronto to Chicago, returning Sun, Feb 15, priced at CA $271 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
YYZ
Toronto
ORD
Chicago
CA $275 Roundtrip, found 2 days ago
CA $275
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Jan 17 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $275 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
YYZ
Toronto
ORD
Chicago
CA $278 Roundtrip, found 2 days ago
CA $278
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 17 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $278 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
YYZ
Toronto
ORD
Chicago
CA $286 Roundtrip, found 2 days ago
CA $286
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 17 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $286 found 2 days ago
Sun, Dec 28 - Tue, Jan 6
YYZ
Toronto
ORD
Chicago
CA $289 Roundtrip, found 3 days ago
CA $289
Roundtrip
found 3 days ago
Select United flight, departing Sun, Dec 28 from Toronto to Chicago, returning Tue, Jan 6, priced at CA $289 found 3 days ago
Wed, Nov 19 - Wed, Dec 10
YYZ
Toronto
ORD
Chicago
CA $292 Roundtrip, found 23 hours ago
CA $292
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Wed, Nov 19 from Toronto to Chicago, returning Wed, Dec 10, priced at CA $292 found 23 hours ago
Thu, Jan 15 - Sun, Feb 15
YYZ
Toronto
ORD
Chicago
CA $294 Roundtrip, found 2 days ago
CA $294
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jan 15 from Toronto to Chicago, returning Sun, Feb 15, priced at CA $294 found 2 days ago

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

Price found within the past 48 hours. Click for updated prices.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Price was CA $1,805, price is now CA $819 per person
CA $819
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $1,874, price is now CA $1,183 per person
CA $1,183
per person
Dec 26 - Jan 2
found 22 hours 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 $1,616, price is now CA $1,176 per person
CA $1,176
per person
Dec 26 - Jan 2
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was CA $1,333, price is now CA $980 per person
CA $980
per person
Dec 19 - Dec 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Price was CA $2,016, price is now CA $1,488 per person
CA $1,488
per person
Dec 11 - Dec 14
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) 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.