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YYZ - CHI

C$ 182 Find cheap flights from Toronto Pearson Airport 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 Pearson Intl to Chicago departing on 12/6. 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
0 bags
Sat 29/6
Sat 6/7

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago.
In the last 7 days, travellers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals from Pearson Intl to Chicago (YYZ-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pearson Intl 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 and deals for you by selecting your travel dates.
Choose your dates
7:00 a.m. - 7:57 a.m.YYZ-ORD
1h 57mdirect
7:10 a.m. - 9:58 a.m.ORD-YYZ
1h 48mdirect
C$ 313United Airlines
Find Deal
Wed, 19 Jun - Wed, 26 Jun
12:30 p.m. - 6:34 p.m.YYZ-ORD
7h 04m1 stop
1:25 p.m. - 10:50 p.m.ORD-YYZ
8h 25m1 stop
C$ 322Delta
Find Deal
Fri, 14 Jun - Mon, 17 Jun
8:05 a.m. - 9:01 a.m.YYZ-ORD
1h 56mdirect
6:00 p.m. - 8:43 p.m.ORD-YYZ
1h 43mdirect
C$ 338Air Canada
Find Deal
Mon, 30 Sep - Sat, 12 Oct
7:40 a.m. - 8:36 a.m.YYZ-ORD
1h 56mdirect
3:35 p.m. - 10:32 p.m.ORD-YYZ
5h 57m1 stop
C$ 339
Find Deal
Tue, 2 Jul - Mon, 8 Jul
6:30 a.m. - 10:01 a.m.YYZ-ORD
4h 31m1 stop
3:35 p.m. - 10:32 p.m.ORD-YYZ
5h 57m1 stop
C$ 348Air Canada
Find Deal
Wed, 24 Jul - Sat, 27 Jul
1:20 p.m. - 2:15 p.m.YYZ-ORD
1h 55mdirect
8:30 a.m. - 2:59 p.m.ORD-YYZ
5h 29m1 stop
C$ 349American Airlines
Find Deal
Tue, 18 Jun - Fri, 21 Jun
11:55 a.m. - 12:50 p.m.YYZ-ORD
1h 55mdirect
6:01 a.m. - 2:30 p.m.ORD-YYZ
7h 29m1 stop
C$ 352American Airlines
Find Deal
Tue, 18 Jun - Wed, 26 Jun
1:45 p.m. - 11:15 p.m.YYZ-ORD
10h 30m1 stop
3:35 p.m. - 10:32 p.m.ORD-YYZ
5h 57m1 stop
C$ 371
Find Deal
Tue, 2 Jul - Sat, 6 Jul
6:15 a.m. - 11:44 a.m.YYZ-MDW
6h 29m1 stop
3:45 p.m. - 9:58 p.m.MDW-YYZ
5h 13m1 stop
C$ 430WestJet
Find Deal
Sat, 10 Aug - Tue, 13 Aug
7:30 p.m. - 3:05 p.m.YYZ-ORD
20h 35m1 stop
6:05 a.m. - 11:12 p.m.ORD-YYZ
16h 07m1 stop
C$ 432WestJet
Find Deal
Tue, 2 Jul - Fri, 5 Jul

Flights from Pearson Intl to Chicago - Travel Insights & Trends

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

What is the cheapest Toronto Pearson Intl Airport to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Toronto Pearson Intl Airport to Chicago.
Our data shows that the cheapest route for a one-way flight from Toronto Pearson Intl Airport to Chicago cost C$ 220 and was between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is C$ 381.

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

The average price of all flights from Toronto Pearson Intl Airport to Chicago clicked on KAYAK for each day over the last 12 months.
For Toronto Pearson Airport to Chicago, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Toronto Pearson Airport, the best deals are generally found on Tuesday, with Sunday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Toronto Pearson Intl Airport to Chicago, 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 is April, where tickets cost C$ 327 on average. On the other hand, the most expensive months are September and August, where the average cost of tickets is C$ 457 and C$ 456 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Toronto Pearson Intl Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Toronto Pearson Intl Airport to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 37 days before departure.

Which airlines provide the cheapest flights from Toronto Pearson Airport to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, United Airlines offered the best one-way deal for that route, at C$ 200. KAYAK users also found Toronto Pearson Airport to Chicago round-trip flights on United Airlines from C$ 313 and on Delta from C$ 322.

Which airlines fly most frequently between Toronto Pearson Airport and Chicago?

United Airlines connects Toronto Pearson Airport to Chicago up to 10 flights per day, followed by American Airlines (5 flights per day), and Air Canada (4 flights per day).

Which airlines fly direct between Toronto Pearson Intl Airport and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Toronto Pearson Intl Airport to Chicago.
There are 3 airlines that fly direct from Toronto Pearson Intl Airport to Chicago. They are: Air Canada, American Airlines and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at C$ 260. On average, the best prices for this route can be found at Air Canada.

How many flights are there between Toronto Pearson Intl Airport and Chicago per day?

Each day, there are between 17 and 20 nonstop flights that take off from Toronto Pearson Intl Airport and land in Chicago, with an average flight time of 1h 57m. The most common departure time is 7:00 a.m. and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 133 flights. The most frequent day of departure is Thursday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Toronto Pearson Intl Airport and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Toronto Pearson Airport to Chicago take?

Direct flights from Toronto Pearson Airport generally make it to Chicago in 1h 53m. The flying distance between the two cities is 1,099 km.

What’s the earliest departure time from Toronto Pearson Airport to Chicago?

Early birds can take the earliest flight from Toronto Pearson Intl Airport at 6:30 am and will be landing in Chicago at 7:25 am.

What’s the latest departure time from Toronto Pearson Airport to Chicago?

If you prefer to fly at night, the latest flight from Toronto Pearson Intl Airport to Chicago jets off at 9:00 pm and lands at 10:02 pm.

Good to know

Low season

January

High season

May

Cheapest flight

C$ 182
Best time to beat the crowds (19% less expensive on average)
Most popular time to fly and prices are also 4% lower on average.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

When to book flights from Pearson Intl to Chicago

Are your dates flexible? Find out the best times to travel from Pearson Intl to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips 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.

FAQs for booking Toronto Pearson Airport to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago was C$ 133 for a one-way ticket and C$ 229 for a round-trip.

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

    When flying out of Toronto Pearson Airport you will be using Toronto Pearson Intl. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

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

  • Which airline alliances offer flights from Toronto Pearson Airport to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Toronto Pearson Airport and Chicago, with oneworld being the most commonly used for this route.

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

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

  • Which is the best airline for flights from Toronto to Chicago, WestJet or United Airlines?

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are WestJet and United Airlines. With an average price for the route of C$ 526 and an overall rating of 7.5, WestJet is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 492 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Toronto Pearson Airport 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 Pearson Airport to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Toronto Pearson Airport 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 Pearson Airport to Chicago?

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Pearson Airport 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 Pearson Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Toronto to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 285 or less one-way and C$ 641 or less round-trip.

Prefer to fly non-stop from Toronto Pearson Airport to Chicago?

Find which airlines fly direct from Pearson Intl to Chicago, which days they fly and book direct flights.

Nonstop departures

Toronto Pearson Intl to Chicago

Monday

ANA,Air Canada,Air New Zealand, +11 more

ANA,Air Canada, +12 more

Tuesday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Wednesday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Thursday

ANA,Air Canada,Air New Zealand, +11 more

ANA,Air Canada, +12 more

Friday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Saturday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Sunday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

See more nonstop flights

Nonstop returns

Chicago to Toronto Pearson Intl

Monday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Tuesday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Wednesday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Thursday

ANA,Air Canada,Air New Zealand, +12 more

ANA,Air Canada, +13 more

Friday

ANA,Air Canada,Air New Zealand, +14 more

ANA,Air Canada, +15 more

Saturday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

Sunday

ANA,Air Canada,Air New Zealand, +13 more

ANA,Air Canada, +14 more

See more nonstop flights
See more nonstop flights

Top 5 airlines serving from Pearson Intl 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 Pearson Intl 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.
7.5
WestJetOverall score based on 2866 reviews
7.3Comfort
8.1Crew
7.7Boarding
6.4Entertainment
6.4Food
Airline reviews

The Priority check in in Toronto rivalled the poorest I've experienced. The young woman at the desk (7:30 AM, YYZ) was unfriendly and abrupt, behaving as though we were interrupting her day. Her inch long fingernails said it all....I really don't belong here. Other than that, WestJet personnel provided a good travel experience, especially in flight. I must say that the repeated announcements about the cabin being full and how folks should gate check their bags became tedious. WestJet should just offer free checked luggage and charge for carry on suitcases. It would save a lot of time and the voices of the gate agents.

10.0 ExcellentCameron, May 2024YYZ - YYC
Read more about WestJet reviews

The Priority check in in Toronto rivalled the poorest I've experienced. The young woman at the desk (7:30 AM, YYZ) was unfriendly and abrupt, behaving as though we were interrupting her day. Her inch long fingernails said it all....I really don't belong here. Other than that, WestJet personnel provided a good travel experience, especially in flight. I must say that the repeated announcements about the cabin being full and how folks should gate check their bags became tedious. WestJet should just offer free checked luggage and charge for carry on suitcases. It would save a lot of time and the voices of the gate agents.

It was very, very cold extremely uncomfortable almost unbearable I was sitting at the front of the cabin

Nice smooth flight with pleasant stewards. Slept most of the flight, they could have slowly turned on the lights to make it more pleasant. Otherwise a good trip.

Great! No food was available during the flight due to the catering service strike but snacks were given throughout the flight which was nice.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Crew was rude.didn’t even say hi or welcome to board

Nothing special. Unacceptable wait for baggage on arriving in Calgary

Departure delay on a late night flight. Made us even later. Tired but got home.

Westjet forced me to put my carry-on baggage in check-in probably because I was assigned seat 23A (the last row seat), which had no cabin space, which is unfair. I wanted to carry on my luggage so that I don't have to wait at the airport for my luggage. Also, because there was no cabin space, I was forced to keep my laptop bag under the seat, which I didn't want to as I was carrying 2 laptops and charger. The airline should basically tell people that if you are assigned a last row seat, then you are not allowed a cabin baggage or a personal item.

Easy processing, flight time was quick and staff was professional and kind.

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

We enjoyed that we boarded and took off on time. We didn’t like that our connection flight was a twenty minute walk through the airport with only one hour in between flights.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

Two flights,both poor. No entertainment. Cramped and uncomfortable seats, little space, the rest was OK. Staff were acceptable good.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The crew was doing their best on an old plane needing updating. Chairs that creaked and wouldn’t stay in position. My tray table was unusable as was on-board entertainment due the audio needing usb earphones (that were not provided). Prior to boarding in Toronto and despite being scheduled for a wheelchair and assistance, we were dropped off by clubcar without a wheelchair which I found myself by a gate. Due to no boarding gate assigned at that time we waited and when it was, it subsequently was moved from 64 to 95. No help could be found so I pushed my husband’s chair to that furthest gate in the airport at the highest speed possible for a 73 year old. And by that I mean I ran. It was a very stressful experience.

Wifi wasn't working on one of the UA flights after boarding.

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Air Canada had a lot of delays on our flight going back to Seattle. So much inconvenience for a long trip.

The Carry-on luggage that approved by TSA and all other airlines,- always an issue with Air Canada. This is inappropriate as my carry on suitcase meets the requirements however it always asked to check in on AC flight on the gate. Yes I have it for free, but it takes extra time to pick up on the carousel. Apparently it fit the overhead space, so why AC has this issue all the time?

The terminal this flight boarded from was so far away, poorly temperature controlled, and generally uncomfortable. The plane was small but the flight was short, so it wasn't so bad.

Seriously need to improve the time schedule and the plans

Great TV, easy boarding, wonderful ground crew and flight crew.

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

It was an excellent experience, traveling from Toronto to Denver with United.

Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
12/6Wed
1 stop
12h 10mYYZ-ORD
C$ 182
11/6Tue
1 stop
10h 58mYYZ-ORD
C$ 193
13/6Thu
directUnited Airlines
1h 54mYYZ-ORD
C$ 200
12/6Wed
directAir Canada
1h 54mYYZ-ORD
C$ 201
31/8Sat
1 stopAir Canada
6h 12mYYZ-ORD
C$ 209
18/6Tue
1 stopUnited Airlines
5h 35mYYZ-ORD
C$ 222
9/7Tue
1 stopAmerican Airlines
5h 36mYYZ-ORD
C$ 224
30/7Tue
1 stopAmerican Airlines
5h 04mYYZ-ORD
C$ 226
5/7Fri
2 stopsWestJet
17h 20mYYZ-ORD
C$ 241
31/8Sat
1 stopWestJet
7h 08mYYZ-MDW
C$ 241

Search by stops

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Last minute flights from Pearson Intl to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
4/6Tue
multi-stopDelta
4h 02mYYZ-MDW
5/6Wed
multi-stopDelta
6h 37mMDW-YYZ
C$ 465
4/6Tue
multi-stopDelta
6h 44mYYZ-ORD
25/6Tue
multi-stopDelta
8h 25mORD-YYZ
C$ 494
1/6Sat
directAmerican Airlines
1h 55mYYZ-ORD
13/6Thu
directAmerican Airlines
1h 50mORD-YYZ
C$ 508
4/6Tue
multi-stop
13h 34mYYZ-ORD
7/6Fri
multi-stop
17h 43mORD-YYZ
C$ 517
1/6Sat
multi-stopAmerican Airlines
5h 39mYYZ-ORD
13/6Thu
directAmerican Airlines
1h 50mORD-YYZ
C$ 527
4/6Tue
directAir Canada
1h 54mYYZ-ORD
5/6Wed
directAir Canada
1h 45mORD-YYZ
C$ 534
4/6Tue
multi-stopAir Canada
7h 16mYYZ-ORD
25/6Tue
directAir Canada
1h 48mORD-YYZ
C$ 556
3/6Mon
multi-stopWestJet
13h 13mYYZ-ORD
7/6Fri
multi-stopWestJet
4h 33mORD-YYZ
C$ 609
3/6Mon
multi-stopWestJet
4h 31mYYZ-ORD
13/6Thu
multi-stopWestJet
9h 54mORD-YYZ
C$ 620
31/5Fri
directUnited Airlines
1h 56mYYZ-ORD
1/6Sat
multi-stopUnited Airlines
5h 55mORD-YYZ
C$ 705

Search by stops

Search by airline

Search by price

Toronto Pearson Airport - Chicago Flights

Departure:

Toronto Pearson Airport (YYZ)Canada

Return flight deals:

Chicago - Toronto Pearson Airport

Cabin classes:

C$ 1,010
C$ 1,420
C$ 1,407
C$ 380