YYZ - ORD

£94 Find Cheap Flights from Toronto to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 23/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
Travellers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 29% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest return fare
£154
Typical prices: £253-£166
United Airlines
Fri 22/5Mon 25/5
YYZ - ORD • Direct
Cheapest one-way flight
£94
Typical prices: £104-£157
United Airlines
Sat 23/5
YYZ - ORD • Direct
Advice from real travellers
AI-powered summary based on content written by travel experts and KAYAK users. AI can make mistakes.
Air Canada's extra legroom seats enhance short flights.
United's carry-on size is smaller for US-bound flights.
Expert advice
Expert advice
+1
+1
Expert advice
Expert advice
+1
Top airlines
United Airlines
Cheapest • from £154 (return)
Air Canada
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Every day
You can fly direct with Air Canada, American Airlines, and United Airlines. Average duration is 2h 03m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
United Airlines
Most punctual • 92% on-time
Night flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 14% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Toronto to Chicago (YYZ-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Toronto to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Toronto to Chicago

Fri, 22 May - Mon, 25 May
United Airlines Logo
10:15 - 11:21
YYZ
-
ORD
2h 06mdirect
United Airlines Logo
21:20 - 23:59
ORD
-
YYZ
1h 39mdirect
£154United Airlines
Thu, 28 May - Thu, 4 Jun
United Airlines Logo
08:50 - 09:50
YYZ
-
ORD
2h 00mdirect
United Airlines Logo
07:09 - 09:54
ORD
-
YYZ
1h 45mdirect
£155United Airlines
Wed, 20 May - Wed, 27 May
United Airlines Logo
19:43 - 23:44
YYZ
-
ORD
5h 01m
1 stop
United Airlines Logo
07:09 - 09:54
ORD
-
YYZ
1h 45mdirect
£159United Airlines
Sat, 23 May - Sun, 31 May
United Airlines Logo
19:43 - 23:26
YYZ
-
ORD
4h 43m
1 stop
United Airlines Logo
21:20 - 23:59
ORD
-
YYZ
1h 39mdirect
£160United Airlines
Sat, 6 Jun - Tue, 16 Jun
United Airlines Logo
19:43 - 23:26
YYZ
-
ORD
4h 43m
1 stop
United Airlines Logo
07:09 - 09:54
ORD
-
YYZ
1h 45mdirect
£165United Airlines
Tue, 2 Jun - Sat, 6 Jun
Air Canada Logo
16:00 - 16:59
YYZ
-
ORD
1h 59mdirect
Air Canada Logo
20:20 - 23:03
ORD
-
YYZ
1h 43mdirect
£166Air Canada
Sat, 23 May - Sat, 30 May
Delta Logo
06:10 - 08:45
YYZ
-
ORD
3h 35m
1 stop
Delta Logo
09:25 - 13:30
ORD
-
YYZ
3h 05m
1 stop
£167Delta
Fri, 22 May - Tue, 26 May
United Airlines Logo
13:00 - 14:06
YYZ
-
ORD
2h 06mdirect
United Airlines Logo
21:55 - 10:04
ORD
-
YYZ
11h 09m
1 stop
£169United Airlines
Thu, 4 Jun - Mon, 8 Jun
United Airlines Logo
07:00 - 08:00
YYZ
-
ORD
2h 00mdirect
United Airlines Logo
21:15 - 23:59
ORD
-
YYZ
1h 44mdirect
£170United Airlines
Thu, 21 May - Mon, 25 May
United Airlines Logo
07:00 - 08:00
YYZ
-
ORD
2h 00mdirect
United Airlines Logo
21:20 - 23:59
ORD
-
YYZ
1h 39mdirect
£170United Airlines
Booking Insights

KAYAK’s insights & trends for Toronto to Chicago flights

Get data-powered insights and trends into flights from Toronto to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a return flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest return trip price found on KAYAK in the last 12 months by searching for a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport departing in May.

What’s the cheapest day of the week to fly from Toronto to Chicago?

The average price of all round-trip flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Tuesdays for the best deals.

What is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is January, where tickets cost £189 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is £245 and £242 respectively.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, you should book around 4 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Find deals
Expert advice

Expert advice for your flight from Toronto to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, The Points Guy, and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Air Canada, ORD and YYZ

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Read more
Duncan Madden

Duncan Madden

Expert on British Airways

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Read more

Good to know - Cheap tickets from Toronto to Chicago

Low seasonJanuary
Cheapest flight£94
Best time to beat the crowds (14% less expensive on average)
Most popular time to fly and prices are also 11% lower on average.
Flight from Toronto to Chicago

When to book flights from Toronto to Chicago

Are your dates flexible? Find out the best times to travel from Toronto to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

Flights from Toronto to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travellers who flew the route from Toronto to Chicago 
Learn how KAYAK collects reviews and tips from users.
BrianFlew with Air CanadaOct 2024
Be prepared for a labyrinthine experience traversing the various levels and passages of the Toronto airport. Bring quality walking shoes, as it is likely well over a km in total walking time.
Verified travelerFlew with United AirlinesMar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

FAQs for booking Toronto to Chicago flights

  • What is the cheapest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport was £94 for a one-way ticket and £154 for a return.

  • Which airports will I be using when flying from Toronto to Chicago?

    Toronto airport is called Toronto Pearson Intl and the only airport in Chicago is Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Toronto to Chicago?

    Air Canada, and United Airlines offer inflight Wi-Fi service on the Toronto to Chicago flight route.

  • Which aircraft models fly most regularly from Toronto to Chicago?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Toronto to Chicago flight route.

  • Which airline alliances offer flights from Toronto to Chicago?

    Star Alliance is the only airline alliance operating flights between Toronto and Chicago.

  • On which days can I fly direct from Toronto to Chicago?

    There are direct flights from Toronto to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Toronto to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Toronto is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Toronto with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Toronto up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport

  • Looking for a cheap flight from Chicago to Toronto? 25% of our users found flights on this route for Chicago or less round-trip.

Prefer to fly direct from Toronto to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto Pearson Intl to Chicago O'Hare Intl.
Find which airlines fly direct from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Chicago O'Hare Intl

Monday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Tuesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Wednesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Thursday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Friday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Saturday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Sunday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Toronto Pearson Intl

Monday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Tuesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Wednesday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Thursday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Friday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Saturday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

Sunday

Air Canada,American Airlines,United Airlines

Air Canada,American Airlines, +1 more

See more direct flights

Reviews of the top airline flying from Toronto to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 10982 reviews
7.8Crew
7.3Boarding
6.3Food
7.1Comfort
6.8Entertainment
Airline reviews

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

10.0 ExcellentAnonymous, Apr 2026
YYZ - EWR
Read more Air Canada reviews

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Everything you need to know for your flight from Toronto to Chicago

Information on your arrival and departure airports

Toronto (YYZ)
O'Hare Intl (ORD)