$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 11/12. 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

KAYAK searches hundreds of travel sites at once for deals on flights from Chicago to Mississauga

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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

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

Free to useThere are no hidden charges or fees.

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

Flight Deals
Useful Info
Flight Deals

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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Mississauga

Fri, Nov 14 - Sun, Nov 16
Air Canada Logo
2:00 pm - 4:39 pmORD-YYZ
1h 39mnonstop
Air Canada Logo
8:15 am - 9:13 amYYZ-ORD
1h 58mnonstop
$150Air Canada
Find Deal
Fri, Nov 7 - Fri, Nov 7
United Airlines Logo
1:19 pm - 4:02 pmORD-YYZ
1h 43mnonstop
United Airlines Logo
7:40 pm - 11:43 pmYYZ-ORD
5h 03m1 stop
$159United Airlines
Find Deal
Fri, Nov 7 - Mon, Nov 10
United Airlines Logo
4:50 pm - 7:45 pmORD-YYZ
1h 55mnonstop
United Airlines Logo
5:30 pm - 6:39 pmYYZ-ORD
2h 09mnonstop
$168United Airlines
Find Deal
Sat, Oct 4 - Sat, Oct 4
American Airlines Logo
6:10 am - 11:59 amORD-YYZ
4h 49m1 stop
American Airlines Logo
3:11 pm - 4:05 pmYYZ-ORD
1h 54mnonstop
$173American Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Air Canada Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
Air Canada Logo
2:10 pm - 3:04 pmYYZ-ORD
1h 54mnonstop
$176Air Canada
Find Deal
Fri, Nov 7 - Sun, Nov 9
United Airlines Logo
2:39 pm - 11:46 pmORD-YYZ
8h 07m1 stop
United Airlines Logo
8:55 am - 10:00 amYYZ-ORD
2h 05mnonstop
$177United Airlines
Find Deal
Sat, Oct 4 - Sat, Oct 4
American Airlines Logo
6:10 am - 11:59 amORD-YYZ
4h 49m1 stop
American Airlines Logo
3:45 pm - 8:27 pmYYZ-ORD
5h 42m1 stop
$189American Airlines
Find Deal
Thu, Oct 2 - Sat, Oct 11
Delta Logo
6:00 am - 4:08 pmORD-YYZ
9h 08m1 stop
Delta Logo
6:09 pm - 8:23 pmYYZ-ORD
3h 14m1 stop
$233Delta
Find Deal
Wed, Oct 29 - Sat, Nov 1
Delta Logo
9:35 am - 5:19 pmMDW-YYZ
6h 44m1 stop
Delta Logo
12:15 pm - 5:55 pmYYZ-MDW
6h 40m1 stop
$233Delta
Find Deal
Thu, Oct 2 - Sun, Oct 5
Lufthansa Logo
7:10 am - 9:58 amORD-YYZ
1h 48mnonstop
Lufthansa Logo
7:00 am - 7:58 amYYZ-ORD
1h 58mnonstop
$238Lufthansa
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 3% increase in price.
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 38m.

  • How many flights are there between Chicago and Mississauga?

    72 direct flights run between Chicago and Mississauga on a daily basis. On average, there are about 510 departures each week.

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

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

  • 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. Air Canada offered a round-trip connection from $150 and United Airlines from $159.

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 1 week before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is June.

Reviews of the 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 332 reviews
7.0Entertainment
8.7Crew
8.2Boarding
8.0Comfort
7.6Food
Airline reviews

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

2.0 MediocreKirsten, Aug 2025BOS - YOW
Read more Porter Airlines reviews

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

Refreshments and Air Hostess was good. Issues with customs in Toronto caused flight to depart and left me behind twice. Vouchers for delayed flight needs to increase.

Long wait to check in at the priority counter in Toronto

I had no communication, receipt etc from Air Canada until hours before flight

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

We had a very long delay. First the inbound flight took a while, then maintenance, they “fixed it” to then do boarding and leave the gate, and waste a lot of time to have to go back to the gate and eventually deplane. Had to wait for a new aircraft, wait for a gate, and do the whole thing again. Instead of leaving at 9:50am we left until past 1. I could’ve not woken up at 5am, or spend some more time with my family if they gave more grace period of time between flights to give some time in case of any issues. But they have to make all and every dollar possible

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Bad experience boarding and flight got delayed didn’t make it to my next flight

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

Complete your trip to Mississauga with a hotel stay or car rental

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.