$59 Find Cheap Flights from Chicago to Mississauga

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Mississauga departing on 9/2. 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.
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Cheap Flights from Chicago to Mississauga (CHI-YYZ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Mississauga 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 round-trip flight deals from Chicago to Mississauga

Tue, Sep 9 - Wed, Sep 10
United Airlines Logo
9:31 pm - 10:04 amORD-YYZ
11h 33m1 stop
United Airlines Logo
1:00 pm - 2:01 pmYYZ-ORD
2h 01mnonstop
$154United Airlines
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Tue, Oct 7 - Thu, Oct 9
Air Canada Logo
6:20 pm - 9:02 pmORD-YYZ
1h 42mnonstop
Air Canada Logo
1:00 pm - 2:01 pmYYZ-ORD
2h 01mnonstop
$164Air Canada
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Tue, Sep 23 - Sat, Sep 27
Air Canada Logo
9:55 am - 12:37 pmORD-YYZ
1h 42mnonstop
Air Canada Logo
10:00 am - 10:53 amYYZ-ORD
1h 53mnonstop
$168Air Canada
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Thu, Sep 18 - Wed, Sep 24
United Airlines Logo
9:31 pm - 10:04 amORD-YYZ
11h 33m1 stop
United Airlines Logo
5:15 pm - 6:12 pmYYZ-ORD
1h 57mnonstop
$177United Airlines
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Tue, Jul 15 - Tue, Jul 15
American Airlines Logo
6:00 am - 12:05 pmORD-YYZ
5h 05m1 stop
American Airlines Logo
3:45 pm - 9:31 pmYYZ-ORD
6h 46m1 stop
$206American Airlines
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Fri, Sep 5 - Thu, Sep 11
American Airlines Logo
5:00 am - 11:09 amORD-YYZ
5h 09m1 stop
American Airlines Logo
7:35 am - 2:06 pmYYZ-ORD
7h 31m1 stop
$210American Airlines
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Tue, Sep 23 - Wed, Oct 1
Delta Logo
6:00 am - 11:29 amORD-YYZ
4h 29m1 stop
Delta Logo
2:40 pm - 7:17 pmYYZ-ORD
5h 37m1 stop
$234Delta
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Tue, Sep 23 - Tue, Sep 30
Delta Logo
5:59 pm - 10:58 pmMDW-YYZ
3h 59m1 stop
Delta Logo
3:59 pm - 6:36 pmYYZ-MDW
3h 37m1 stop
$234Delta
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Tue, Aug 12 - Sat, Aug 23
WestJet Logo
9:15 am - 8:54 pmMDW-YYZ
10h 39m2 stops
WestJet Logo
6:30 pm - 9:16 amYYZ-MDW
15h 46m2 stops
$437WestJet
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Fri, Aug 8 - Mon, Aug 11
WestJet Logo
12:43 pm - 10:19 amMDW-YYZ
20h 36m1 stop
WestJet Logo
6:30 pm - 9:16 amYYZ-MDW
15h 46m2 stops
$438WestJet
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$59
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago O'Hare Airport to Toronto Pearson Airport

When to book flights from Chicago to Mississauga

Are your dates flexible? Find out the best times to travel from Chicago to Mississauga based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Mississauga

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

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Mississauga does not have its own airport so you’ll be flying into nearby Toronto Pearson Intl airport, which is 6.3 mi away.

  • How long does a flight from Chicago to Mississauga take?

    Direct flights cover the 424 miles separating Chicago and Mississauga in about 1h 41m.

  • How many flights are there between Chicago and Mississauga?

    64 direct flights run between Chicago and Mississauga on a daily basis. On average, there are about 453 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Mississauga?

    Consider leaving on a Tuesday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Wednesdays.

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

    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 Chicago to Mississauga.

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

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

    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 Mississauga with an airline and back to Chicago with another airline.

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

    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 Mississauga from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Mississauga?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Mississauga found on KAYAK was with United Airlines for $59. United Airlines offered a round-trip connection from $154 and Air Canada from $164.

Top tips for finding cheap flights from Chicago to Mississauga

  • There is no airport in Mississauga. Instead, you’ll be flying into Toronto Pearson Airport when flying between Chicago and Mississauga.
  • The cheapest flight from Chicago to Mississauga was found 68 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be October, November and December. The cheapest month to fly is April.

Top 4 airlines serving Chicago to Mississauga

 
Need help choosing which airline to fly with from Chicago to Mississauga? 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.
8.0
Porter AirlinesOverall score based on 288 reviews
7.6Food
8.2Boarding
8.1Comfort
7.0Entertainment
8.7Crew
Airline reviews

I love the 2 seats per row. More room. The crew were excellent.

10.0 ExcellentAnonymous, Apr 2025YHZ - YOW
Read more Porter Airlines reviews

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Flight was delayed but the real issue is how long we sat after boarding. Space very limited for an overnight flight and seatbacks didn’t recline so it was almost impossible to sleep.

The staff made sure I was comfortable, moved me to a better seat with more leg room

Somehow, my booking was under my preferred name instead of my legal name so they almost didn’t let me board the plane at LAX. This problem should have been notified to me when I was still in Toronto.

When arriving over 2 hours early to check k in at Charlotte airport I was told I would have to check my carry on ? Apparently the flight was full and may not be room. I was not given a choice and the agent was quite unpleasant about it. I am a senior amd was not comfortable me having to worry about my bag being lost vut it didn’t seem to bother him. There were lots and lots of people of all ages in line when we boarded with carryons and most larger than mine .the rest of my journey was pleasant vut this was totally unacceptable.

The layover was 6 PLUS hours and we were only given a $15.00 voucher. We missed our first activity in Quebec due to the delay.

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

It was a short flight, and no entertainment. That was not a problem for us, but there is no option for "not applicable". There was a bit of turbulence, so there was no food service.

the fact air Canada changed my flight from 850 PM to 815 AM with zero regard to the plans i made that last day, the cost i lost out on as things were non refundable amd shortening my first vacation in 7 years sickened me. when we purchase a service thats whats we expect. when we want to change the service we have to pay for that option but you do whatever you want . i called accessibility dept as i have a cpap and an implanted loop recorder first person said no problem just let security know you cant go thru scanners. then i got an email saying i had to fill out a fit to fly form . which again there was NO need to have that none. But that cost me money and time to have a doctor fill it out. then when i went to check in online i was declined i had to see a person at the airport instead. i couldnt get my boarding pass like everyone elseso here I was contacting air canada so I would have a easy travel experience and it ended up being a nightmare with more work for me, more cost and time. the flight itself was great the nightmare around it i will never subject myself to again. i tried to stick with supporting Canada but Air Canada was not worth supporting. very disappointed especially with a dept that is supposed to help disabled people not make an already challenging event not worth going thru at all.

Most courteous, helpful employees and all flights were on time.

All was good except for the seats, not very comfy.

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

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