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

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

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

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $299 round trip and CA $195 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Mar 18 - Wed, Mar 25
YYZ
Toronto
ORD
Chicago
CA $299 Roundtrip, found 12 hours ago
CA $299
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, Mar 18 from Toronto to Chicago, returning Wed, Mar 25, priced at CA $299 found 12 hours ago
Fri, May 8 - Sat, May 9
YYZ
Toronto
ORD
Chicago
CA $299 Roundtrip, found 14 hours ago
CA $299
Roundtrip
found 14 hours ago
Select Air Canada flight, departing Fri, May 8 from Toronto to Chicago, returning Sat, May 9, priced at CA $299 found 14 hours ago
Mon, May 11 - Mon, May 11
YYZ
Toronto
ORD
Chicago
CA $299 Roundtrip, found 14 hours ago
CA $299
Roundtrip
found 14 hours ago
Select Delta flight, departing Mon, May 11 from Toronto to Chicago, returning Mon, May 11, priced at CA $299 found 14 hours ago
Wed, May 6 - Tue, May 12
YYZ
Toronto
ORD
Chicago
CA $300 Roundtrip, found 1 day ago
CA $300
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 6 from Toronto to Chicago, returning Tue, May 12, priced at CA $300 found 1 day ago
Mon, May 11 - Wed, May 13
YYZ
Toronto
ORD
Chicago
CA $304 Roundtrip, found 14 hours ago
CA $304
Roundtrip
found 14 hours ago
Select Air Canada flight, departing Mon, May 11 from Toronto to Chicago, returning Wed, May 13, priced at CA $304 found 14 hours ago
Fri, Jun 12 - Sun, Jun 14
YYZ
Toronto
ORD
Chicago
CA $307 Roundtrip, found 8 hours ago
CA $307
Roundtrip
found 8 hours ago
Select Delta flight, departing Fri, Jun 12 from Toronto to Chicago, returning Sun, Jun 14, priced at CA $307 found 8 hours ago
Fri, Mar 20 - Wed, Apr 1
YYZ
Toronto
ORD
Chicago
CA $322 Roundtrip, found 5 days ago
CA $322
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Mar 20 from Toronto to Chicago, returning Wed, Apr 1, priced at CA $322 found 5 days ago
Fri, Mar 27 - Sun, Apr 5
YYZ
Toronto
ORD
Chicago
CA $322 Roundtrip, found 2 days ago
CA $322
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Mar 27 from Toronto to Chicago, returning Sun, Apr 5, priced at CA $322 found 2 days ago
Mon, May 11 - Wed, May 13
YYZ
Toronto
ORD
Chicago
CA $322 Roundtrip, found 14 hours ago
CA $322
Roundtrip
found 14 hours ago
Select United flight, departing Mon, May 11 from Toronto to Chicago, returning Wed, May 13, priced at CA $322 found 14 hours ago
Sat, May 2 - Sat, May 9
YYZ
Toronto
ORD
Chicago
CA $323 Roundtrip, found 2 days ago
CA $323
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, May 2 from Toronto to Chicago, returning Sat, May 9, priced at CA $323 found 2 days ago

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

Price found within the past 48 hours. Click for updated prices.
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
Price was CA $683, price is now CA $558 per person
CA $558
per person
Apr 10 - Apr 13
found 2 hours ago
Roundtrip non-stop flight included
Kitchener (YKF) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Price was CA $914, price is now CA $730 per person
CA $730
per person
Apr 17 - Apr 19
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Price was CA $880, price is now CA $707 per person
CA $707
per person
Apr 17 - Apr 19
found 23 hours ago
Roundtrip flight included
Toronto (YTO) 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 $994, price is now CA $811 per person
CA $811
per person
Mar 21 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was CA $1,076, price is now CA $888 per person
CA $888
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Pearson Intl. to O'Hare Intl.
View all trips

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.