$72 Find Cheap Flights from Chicago to Ontario

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 Ontario departing on 9/15. 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 to Ontario

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Ontario, 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 Chicago to Ontario, as well as popular online travel agencies
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Cheap Flights from Chicago to Ontario

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
Torontononstop$173
Ottawa
Ottawa1 stop$300
Thunder Bay
Thunder Bay2 stops$435
Toronto
Torontononstop$173
Ottawa
Ottawa1 stop$300
Thunder Bay
Thunder Bay2 stops$435

Book Cheap Chicago to Ontario Plane Tickets

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

Fri, Sep 26 - Sun, Sep 28
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$173Porter Airlines
Find Deal
Fri, Oct 3 - Sun, Oct 5
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$174Porter Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$175Porter Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
 Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
 Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Wed, Oct 15 - Sat, Oct 18
 Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
 Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Thu, Oct 2 - Sat, Oct 18
Delta Logo
9:35 am - 5:23 pmMDW-YYZ
6h 48m1 stop
Delta Logo
6:20 am - 1:08 pmYYZ-MDW
7h 48m1 stop
$233Delta
Find Deal
Fri, Nov 21 - Thu, Nov 27
Delta Logo
6:00 am - 5:21 pmMDW-YUL
10h 21m1 stop
Delta Logo
7:00 am - 4:39 pmYUL-MDW
10h 39m1 stop
$236Delta
Find Deal
Mon, Sep 29 - Thu, Oct 2
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$244Air Transat
Find Deal
Thu, Sep 25 - Tue, Sep 30
WestJet Logo
12:43 pm - 9:51 pmMDW-YYZ
8h 08m1 stop
WestJet Logo
1:20 pm - 9:36 pmYYZ-MDW
9h 16m1 stop
$293WestJet
Find Deal
Sat, Sep 27 - Mon, Sep 29
WestJet Logo
1:43 pm - 11:20 pmMDW-YYZ
8h 37m1 stop
WestJet Logo
8:00 pm - 9:40 amYYZ-MDW
14h 40m2 stops
$297WestJet
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Ontario flights

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

What is the cheapest Chicago Midway Airport to Ontario flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Ontario from Chicago Midway Airport found in the last 72 hours was to Toronto, at $78 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Toronto Island Airport (YTZ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $78.

Can I save money by flying with a layover from Chicago Midway Airport to Ontario?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $252, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Ontario?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Ontario, 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 Chicago Midway Airport to Ontario is July, when tickets cost $179 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $381 and $371 respectively.

Good to know

Low seasonJanuary
Cheapest flight$72
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly with an average 27% increase in price.
Flight from Chicago Midway Airport to Toronto Island

FAQs - booking Ontario flights

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

    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 Ontario.

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

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

    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 from Chicago to Ontario with an airline and back with another airline.

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

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

  • What is the cheapest time of day to fly to Ontario?

    The cheapest time of day to fly to Ontario is generally in the evening, when round-trip flights cost $273 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Ontario is generally at night, which is peak travel time and where the average cost of a ticket is $360.

Top tips for finding cheap flights to Ontario

  • Looking for a cheap flight? 25% of our users found tickets from Chicago to the following destinations at these prices or less: Toronto $97 one-way - $192 round-trip

Reviews of the top airline flying from Chicago to Ontario

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Ontario. 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 Chicago to Ontario? 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 359 reviews
8.2Boarding
7.6Food
8.0Comfort
8.6Crew
7.0Entertainment
Airline reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

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!

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

Information on your arrival and departure airports

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