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 $360 round trip and CA $213 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 16 - Mon, Sep 21
YYZ
Toronto
ORD
Chicago
CA $360 Roundtrip, found 1 day ago
CA $360
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 16 from Toronto to Chicago, returning Mon, Sep 21, priced at CA $360 found 1 day ago
Tue, May 26 - Thu, Jun 4
YYZ
Toronto
ORD
Chicago
CA $373 Roundtrip, found 3 days ago
CA $373
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, May 26 from Toronto to Chicago, returning Thu, Jun 4, priced at CA $373 found 3 days ago
Thu, Apr 9 - Sat, Apr 11
YYZ
Toronto
ORD
Chicago
CA $386 Roundtrip, just found
CA $386
Roundtrip
just found
Select American Airlines flight, departing Thu, Apr 9 from Toronto to Chicago, returning Sat, Apr 11, priced at CA $386 just found
Sat, May 16 - Mon, Jun 1
YYZ
Toronto
ORD
Chicago
CA $386 Roundtrip, found 16 hours ago
CA $386
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Sat, May 16 from Toronto to Chicago, returning Mon, Jun 1, priced at CA $386 found 16 hours ago
Wed, Sep 16 - Mon, Sep 21
YYZ
Toronto
ORD
Chicago
CA $388 Roundtrip, found 1 day ago
CA $388
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 16 from Toronto to Chicago, returning Mon, Sep 21, priced at CA $388 found 1 day ago
Thu, Apr 9 - Sat, Apr 11
YYZ
Toronto
ORD
Chicago
CA $394 Roundtrip, just found
CA $394
Roundtrip
just found
Select American Airlines flight, departing Thu, Apr 9 from Toronto to Chicago, returning Sat, Apr 11, priced at CA $394 just found
Mon, May 18 - Mon, Jun 1
YYZ
Toronto
ORD
Chicago
CA $395 Roundtrip, found 16 hours ago
CA $395
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Mon, May 18 from Toronto to Chicago, returning Mon, Jun 1, priced at CA $395 found 16 hours ago
Tue, Apr 28 - Wed, Apr 29
YYZ
Toronto
ORD
Chicago
CA $398 Roundtrip, found 5 days ago
CA $398
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Apr 28 from Toronto to Chicago, returning Wed, Apr 29, priced at CA $398 found 5 days ago
Tue, May 12 - Fri, Jun 5
YYZ
Toronto
ORD
Chicago
CA $400 Roundtrip, found 1 day ago
CA $400
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 12 from Toronto to Chicago, returning Fri, Jun 5, priced at CA $400 found 1 day ago
Mon, May 18 - Mon, Jun 1
YYZ
Toronto
ORD
Chicago
CA $403 Roundtrip, found 16 hours ago
CA $403
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Mon, May 18 from Toronto to Chicago, returning Mon, Jun 1, priced at CA $403 found 16 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 $1,332, price is now CA $909 per person
CA $909
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Price was CA $1,614, price is now CA $1,055 per person
CA $1,055
per person
Apr 30 - May 3
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was CA $1,894, price is now CA $1,278 per person
CA $1,278
per person
May 3 - May 7
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Price was CA $1,491, price is now CA $1,095 per person
CA $1,095
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Price was CA $1,488, price is now CA $1,157 per person
CA $1,157
per person
May 5 - May 8
found 19 hours ago
Roundtrip 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.

Explore More Ways to Travel with 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.