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 $301 round trip and CA $187 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $301 Roundtrip, found 5 hours ago
CA $301
Roundtrip
found 5 hours ago
Select United flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $301 found 5 hours ago
Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $301 Roundtrip, found 5 hours ago
CA $301
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $301 found 5 hours ago
Wed, Apr 1 - Mon, Apr 6
YYZ
Toronto
ORD
Chicago
CA $303 Roundtrip, found 1 day ago
CA $303
Roundtrip
found 1 day ago
Select United flight, departing Wed, Apr 1 from Toronto to Chicago, returning Mon, Apr 6, priced at CA $303 found 1 day ago
Thu, Apr 2 - Sun, Apr 5
YYZ
Toronto
ORD
Chicago
CA $304 Roundtrip, found 1 day ago
CA $304
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Apr 2 from Toronto to Chicago, returning Sun, Apr 5, priced at CA $304 found 1 day ago
Fri, Feb 20 - Mon, Mar 16
YYZ
Toronto
ORD
Chicago
CA $308 Roundtrip, found 4 hours ago
CA $308
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Feb 20 from Toronto to Chicago, returning Mon, Mar 16, priced at CA $308 found 4 hours ago
Thu, Feb 19 - Sun, Mar 15
YYZ
Toronto
ORD
Chicago
CA $310 Roundtrip, found 16 hours ago
CA $310
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Feb 19 from Toronto to Chicago, returning Sun, Mar 15, priced at CA $310 found 16 hours ago
Thu, Feb 26 - Mon, Mar 2
YYZ
Toronto
ORD
Chicago
CA $311 Roundtrip, found 5 hours ago
CA $311
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Toronto to Chicago, returning Mon, Mar 2, priced at CA $311 found 5 hours ago
Fri, Feb 20 - Mon, Mar 16
YYZ
Toronto
ORD
Chicago
CA $319 Roundtrip, found 4 hours ago
CA $319
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Feb 20 from Toronto to Chicago, returning Mon, Mar 16, priced at CA $319 found 4 hours ago
Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $327 Roundtrip, found 5 hours ago
CA $327
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $327 found 5 hours ago
Wed, Jun 17 - Sun, Jun 21
YYZ
Toronto
ORD
Chicago
CA $329 Roundtrip, found 5 hours ago
CA $329
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Jun 17 from Toronto to Chicago, returning Sun, Jun 21, priced at CA $329 found 5 hours ago

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

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $708, price is now CA $530 per person
CA $530
per person
Mar 6 - Mar 8
found 1 day 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 $1,063, price is now CA $790 per person
CA $790
per person
Mar 6 - Mar 8
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 $691, price is now CA $562 per person
CA $562
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Price was CA $1,537, price is now CA $1,269 per person
CA $1,269
per person
Mar 1 - Mar 4
found 1 hour ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was CA $660, price is now CA $546 per person
CA $546
per person
Mar 6 - Mar 8
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.