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YTO - CHI

$110 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 5/7. 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
Sun 5/26
Sun 6/2

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, 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
In the last 7 days travelers have searched 44,738,066 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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Cheap flight deals from Toronto to Chicago (YTO-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 and deals for you by selecting your travel dates.
Choose your dates
6:30 am - 4:35 pmYYZ-ORD
11h 05m1 stop
11:48 am - 7:35 pmORD-YYZ
6h 47m1 stop
Wed, May 15 - Thu, May 16
6:30 am - 4:35 pmYYZ-ORD
11h 05m1 stop
6:40 pm - 10:35 pmORD-YYZ
26h 55m1 stop
Wed, May 8 - Tue, May 14
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
$229Porter Airlines
Find Deal
Thu, May 23 - Thu, May 30
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
8:40 am - 11:22 amMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Thu, May 23 - Sun, May 26
9:00 am - 9:54 amYYZ-ORD
1h 54mnonstop
7:10 am - 9:58 amORD-YYZ
1h 48mnonstop
$254Air Canada
Find Deal
Thu, Jun 20 - Sun, Jun 23
7:00 am - 7:57 amYYZ-ORD
1h 57mnonstop
5:00 pm - 7:52 pmORD-YYZ
1h 52mnonstop
$255United Airlines
Find Deal
Thu, May 23 - Thu, May 30
12:00 pm - 12:54 pmYYZ-ORD
1h 54mnonstop
6:00 am - 8:48 amORD-YYZ
1h 48mnonstop
$257Air Canada
Find Deal
Thu, Aug 22 - Sun, Aug 25
3:10 pm - 4:05 pmYYZ-ORD
1h 55mnonstop
3:20 pm - 10:20 pmORD-YYZ
6h 00m1 stop
$263American Airlines
Find Deal
Fri, May 24 - Fri, May 31
7:59 am - 8:55 amYYZ-ORD
1h 56mnonstop
9:15 pm - 11:58 pmORD-YYZ
1h 43mnonstop
$264United Airlines
Find Deal
Sat, Jun 29 - Mon, Jul 8
7:20 pm - 1:38 amYYZ-ORD
7h 18m1 stop
8:20 pm - 11:10 pmORD-YYZ
1h 50mnonstop
$269American Airlines
Find Deal
Thu, May 23 - Thu, May 30

Flights from Toronto to Chicago - Travel Insights & Trends

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.

What is the cheapest Toronto 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 to Chicago.
Our data shows that the cheapest route for a one-way flight from Toronto to Chicago cost $129 and was between Toronto Island Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $181.

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

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

What is the cheapest month to fly from Toronto to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Toronto 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 to Chicago is January, where tickets cost $231 on average. On the other hand, the most expensive months are July and August, where the average cost of tickets is $339 and $338 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Toronto 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 to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 78 days before departure.

Which airlines provide the cheapest flights from Toronto to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Toronto to Chicago found on KAYAK was with Porter Airlines for $136. Porter Airlines proposed a round-trip connection from $229 and Air Canada from $254.

Which airlines fly most frequently between Toronto and Chicago?

In normal times, American Airlines flies from Toronto to Chicago up to 9 times per day, United Airlines up to 8 times per day, and Air Canada up to 4 times per day.

Which airlines fly non-stop between Toronto and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Toronto to Chicago.
There are 4 airlines that fly nonstop from Toronto to Chicago. They are: Air Canada, American Airlines, Porter Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Porter Airlines at $205 for a one-way flight. On average, the best prices for this route can be found at Porter Airlines.

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

Each day, there are between 23 and 28 nonstop flights that take off from Toronto and land in Chicago, with an average flight time of 1h 56m. The most common departure time is 1:00 pm and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 179 flights. The most frequent day of departure is Sunday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Toronto 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 to Chicago take?

The average nonstop flight takes 1h 47m, covering a distance of 435 miles.

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

Early birds can take the earliest flight from Toronto at 6:30 am and will be landing in Chicago at 7:26 am.

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

If you prefer to fly at night, the latest flight from Toronto to Chicago jets off at 9:00 pm and lands at 10:04 pm.

Good to know

Low season

January

High season

August

Cheapest flight

$110
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

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 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 flights from Toronto to Chicago

  • Can I fly from Toronto to Chicago non-stop?

    Flights from Toronto to Chicago are quite short, usually lasting less than 2 hours, which means they occur regularly and are often non-stop. Direct flights are offered by numerous airlines including American Airlines, Porter Airlines and Air Canada.

  • How do I get from downtown Toronto to Billy Bishop Airport?

    Getting from downtown Toronto to Billy Bishop Airport is simple. Passengers can choose the free express shuttle that goes from Toronto’s city centre to the mainland ferry terminal every 15 minutes. There is then an 800-meter pedestrian tunnel or a 90-second ride on the ferry, both going directly to the airport.

  • Are there on-site hotels at Billy Bishop Airport?

    While there are no airports directly inside Billy Bishop Airport, there are a number of nearby hotels like the Fairmont Royal York or the Strathcona Hotel. Both are located just minutes from Billy Bishop Airport and offer comfortable rooms and a number of amenities.

  • What is there to do at Toronto Pearson International Airport?

    If your plane was delayed or Toronto is just one leg of your journey, Toronto Pearson International Airport offers many opportunities to pass the time. The airport is fully equipped so that you can enjoy a number of shops and kiosks, a workout at Goodlife Fitness or a treatment at the spa. More interested in art? Check out the displays throughout the airport, featuring works by local artists.

  • What is the cheapest flight from Toronto to Chicago?

    In the last 3 days, the lowest price for a flight from Toronto to Chicago was $110 for a one-way ticket and $223 for a round-trip.

  • Do I need a passport to fly between Toronto and Chicago?

    Yes

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

    On your way to Chicago, you’ll fly out from one of these Toronto airports: Toronto Island or Toronto Pearson Intl. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

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

    Air Canada, and American 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?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are Porter Airlines and United Airlines. With an average price for the route of $285 and an overall rating of 7.4, Porter Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $362 and an overall rating of 7.4.

  • 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 travelers 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 round-trip 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.

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 $141 or less one-way and $219 or less round-trip.
  • Flights from Toronto to Chicago usually depart from Lester B. Pearson International Airport, located 22.5 km northwest of Toronto’s city centre, and land at O’Hare International Airport, located 23 km northwest of downtown Chicago. Flights might also depart from the smaller Billy Bishop Toronto City Airport, located on the Toronto Island, and could land at Chicago Midway International Airport, 13 km from the Loop business district in Chicago.
  • Travelling with kids and worried about entertaining them before your flight? Don’t be, Toronto Pearson International Airport offers two child play areas located in both Terminal 1 and Terminal 3. These areas are fully equipped to keep your children occupied with toys, games and books.
  • As Chicago O’Hare is one of the largest airports in the area, it is no surprise that it features a plethora of things to do, should you have some time to spare. To take care of your mind and body, head to the Health Club for a run or to the Yoga Room to relax and stretch. The airport is also home to dozens of shops that offer many options for gifts and souvenirs. If you like art, enjoy the sculptures, paintings and murals scattered throughout the airport. Passengers can also take a walk in the Urban Garden to admire the different plant species present there.
  • If your flight has arrived late and you don’t want to travel into Chicago late at night, book a room at the Hilton Chicago O’Hare Airport Hotel, located across from Terminal 2. Alternatively, you can also stay in one of the hotels located just minutes from the airport such as the Sheraton Chicago O’Hare, the Aloft Chicago O’Hare or the Embassy Suites Chicago O’Hare Rosemont.
  • Getting from Chicago O’Hare to downtown Chicago is quite easy. The Amtrak train connects the airport and the city center in about 40 minutes, and there are also numerous CTA bus lines connecting the airport to various destinations in the city. The L train line also offers a 24-hour service to reach the city centre.
See more tips

Prefer to fly non-stop from Toronto to Chicago?

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

Nonstop departures

Toronto to Chicago

Monday

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

ANA, Air Canada, +14 more

Tuesday

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

ANA, Air Canada, +15 more

Wednesday

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

ANA, Air Canada, +15 more

Thursday

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

ANA, Air Canada, +14 more

Friday

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

ANA, Air Canada, +15 more

Saturday

ANA, Air Canada, Air New Zealand, +15 more

ANA, Air Canada, +16 more

Sunday

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

ANA, Air Canada, +15 more

See more direct flights

Nonstop returns

Chicago to Toronto

Monday

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

ANA, Air Canada, +14 more

Tuesday

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

ANA, Air Canada, +15 more

Wednesday

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

ANA, Air Canada, +15 more

Thursday

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

ANA, Air Canada, +14 more

Friday

ANA, Air Canada, Air New Zealand, +15 more

ANA, Air Canada, +16 more

Saturday

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

ANA, Air Canada, +15 more

Sunday

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

ANA, Air Canada, +15 more

See more direct flights
See more direct flights

Top 4 airlines serving 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.
7.4
Porter AirlinesOverall score based on 438 reviews
8.2crew
7.5comfort
6.6entertainment
7.4food
7.6boarding
Airline reviews

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.

10.0 ExcellentJustin, Apr 2024YVR - YYZ
Read more about Porter Airlines reviews

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.

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

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

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

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.

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

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

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.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

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

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

Once again my complaint is how close the seats are together. Also, the bathrooms were not very clean by the second half of the flight.

Excellent in flight service, perhaps the best we've ever had. Business class feels tired and needs improvement to compete with other airlines. The food looked good but tasted terrible. Check in was quick, the flight arrived early and our luggage was on our flight with us.

The staff were so kind and helpful. We flew back from NY with another airline and it was horrible. We will always stick with Air Canada as everything was far better!

The boarding process in Toronto bad as they share space with domestic flights and when those domestic flights come in you are locked out behind closed doors until they are done and then its a mad rush to get your boarding gates and board. This is not so much due to Air Canada but with the GTAA, but Air Canada could use different gates especially early morning in order to prevent such travel angst.

Terrible quality wifi and they charge a lot for it. They nickel and dime you for everything.

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.
5/7Tue
1 stop
12h 16mYYZ-ORD
$110
5/7Tue
1 stop
12h 16mYYZ-ORD
$113
6/1Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$136
5/24Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$137
6/18Tue
1 stopAir Canada
5h 53mYTZ-ORD
$150
5/24Fri
1 stopAir Canada
5h 53mYTZ-ORD
$151
5/27Mon
nonstopUnited Airlines
1h 54mYYZ-ORD
$151
6/29Sat
nonstopUnited Airlines
1h 56mYYZ-ORD
$160
6/1Sat
nonstopAmerican Airlines
1h 55mYYZ-ORD
$162
5/13Mon
1 stopAmerican Airlines
5h 39mYYZ-ORD
$173

Search by stops

Search by airline

Search by price

Last minute flights from Toronto 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.
4/30Tue
multi-stop
10h 07mYYZ-ORD
5/21Tue
multi-stop
6h 47mORD-YYZ
$322
4/30Tue
multi-stop
10h 07mYYZ-ORD
5/10Fri
multi-stop
24h 32mORD-YYZ
$333
4/27Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
5/8Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$350
4/29Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
5/10Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$351
4/29Mon
nonstopAmerican Airlines
1h 55mYYZ-ORD
5/11Sat
nonstopAmerican Airlines
1h 35mORD-YYZ
$384
4/29Mon
nonstopAmerican Airlines
1h 55mYYZ-ORD
5/11Sat
multi-stopAmerican Airlines
5h 20mORD-YYZ
$392
4/30Tue
nonstopAir Canada
1h 54mYYZ-ORD
5/10Fri
nonstopAir Canada
1h 45mORD-YYZ
$404
4/27Sat
nonstopAir Canada
1h 54mYYZ-ORD
5/8Wed
nonstopAir Canada
1h 45mORD-YYZ
$417
4/27Sat
nonstopUnited Airlines
2h 04mYYZ-ORD
5/13Mon
nonstopUnited Airlines
1h 43mORD-YYZ
$448
4/30Tue
nonstopUnited Airlines
1h 59mYYZ-ORD
5/6Mon
multi-stopUnited Airlines
9h 40mORD-YYZ
$456

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Flights to Chicago

Return flight deals:

Chicago - Toronto

Cabin classes:

$963
$332
$1,527
$181

Compare transportation modes for Toronto to Chicago

Average priceAverage duration
Flights$5771h 47m
Buses$11015h 50m