$105 Cheap Flights from Toronto (YTZ) to Chicago (ORD)

View $105 flight on Mon, Jun 30, 2025Opens in a new window

Popular airlines from Billy Bishop Toronto City Airport (YTZ) to Chicago O'Hare Intl. Airport (ORD)

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Find available prices by choosing your travel dates.

Cheap Flights from Toronto to Chicago (YTZ-ORD)

Prices were available within the past 7 days and start at $105 for one-way flights and $166 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Jul 10 - Fri, Jul 18
YTZ
Toronto
ORD
Chicago
$166 Roundtrip, found 3 days ago
$166
Roundtrip
found 3 days ago
Select Air Canada flight, departing Thu, Jul 10 from Toronto to Chicago, returning Fri, Jul 18, priced at $166 found 3 days ago
Air Canada
Sat, May 10 - Sat, May 24
YTZ
Toronto
ORD
Chicago
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, May 10 from Toronto to Chicago, returning Sat, May 24, priced at $186 found 3 days ago
Air Canada
Tue, May 13 - Sun, May 25
YTZ
Toronto
ORD
Chicago
$195 Roundtrip, found 3 days ago
$195
Roundtrip
found 3 days ago
Select Air Canada flight, departing Tue, May 13 from Toronto to Chicago, returning Sun, May 25, priced at $195 found 3 days ago
Air Canada
Thu, May 22 - Thu, May 29
YTZ
Toronto
ORD
Chicago
$199 Roundtrip, found 7 hours ago
$199
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Thu, May 22 from Toronto to Chicago, returning Thu, May 29, priced at $199 found 7 hours ago
Air Canada
Sat, May 10 - Sun, May 11
YTZ
Toronto
ORD
Chicago
$208 Roundtrip, found 16 hours ago
$208
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Sat, May 10 from Toronto to Chicago, returning Sun, May 11, priced at $208 found 16 hours ago
Air Canada
Sat, May 10 - Sat, May 24
YTZ
Toronto
ORD
Chicago
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, May 10 from Toronto to Chicago, returning Sat, May 24, priced at $215 found 3 days ago
Air Canada
Sat, May 10 - Sat, May 24
YTZ
Toronto
ORD
Chicago
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, May 10 from Toronto to Chicago, returning Sat, May 24, priced at $219 found 3 days ago
Air Canada
Sat, May 10 - Sat, Aug 30
YTZ
Toronto
ORD
Chicago
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, May 10 from Toronto to Chicago, returning Sat, Aug 30, priced at $222 found 3 days ago
Air Canada
Thu, May 22 - Thu, May 29
YTZ
Toronto
ORD
Chicago
$223 Roundtrip, found 7 hours ago
$223
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Thu, May 22 from Toronto to Chicago, returning Thu, May 29, priced at $223 found 7 hours ago
Air Canada
Thu, May 22 - Thu, May 29
YTZ
Toronto
ORD
Chicago
$228 Roundtrip, found 7 hours ago
$228
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Thu, May 22 from Toronto to Chicago, returning Thu, May 29, priced at $228 found 7 hours ago

Frequently asked questions

How much does a flight from Billy Bishop Toronto City Airport (YTZ) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from YTZ to ORD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from YTZ to ORD?
The cheapest flights from YTZ to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Billy Bishop Toronto City Airport (YTZ) to O'Hare Intl. Airport (ORD)?
You can’t fly nonstop from Toronto, ON (YTZ-Billy Bishop Toronto City) to O’Hare Intl. Airport (ORD). However, you can arrive in Chicago without any layovers by departing from Pearson Intl. Airport (YYZ).
What is the cheapest airline that flies from YTZ to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from YTZ to ORD. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Billy Bishop Toronto City Airport (YTZ) to O'Hare Intl. Airport (ORD)?
Direct flights from Billy Bishop Toronto City Airport (YTZ) to O’Hare Intl. Airport (ORD) aren’t available daily, so you’ll have to take a flight with a layover. Explore your options with Expedia’s filters. Enter your dates and pick either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from YTZ to ORD?
Usually you’ll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* But this can vary depending on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Billy Bishop Toronto City Airport (YTZ) to O'Hare Intl. Airport (ORD)?
To land at O’Hare Intl. Airport (ORD) on schedule, book a flight that leaves from Billy Bishop Toronto City Airport (YTZ) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Billy Bishop Toronto City Airport (YTZ)?
If you’re traveling on a direct flight from Billy Bishop Toronto City Airport (YTZ) to Chicago, Midway Intl. Airport (MDW) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Billy Bishop Toronto City Airport (YTZ) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book a flight from YTZ to ORD generally means paying more. While it’s possible to find some last-minute offers, there’s no guarantee. Be flexible with your itinerary to boost your chances of scoring a bargain.
Is it cheaper to book a YTZ to ORD flight and hotel package?
Booking a YTZ to ORD flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our extensive range of accommodations and then add flights, activities and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Billy Bishop Toronto City Airport (YTZ) to O'Hare Intl. Airport (ORD)?
If you booked your YTZ to ORD flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.
*Available to One Key members.