$61 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 8/26. 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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Flight Deals

Cheap Flights from Chicago to Ontario

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
Torontononstop$158
Ottawa
Ottawa1 stop$281
Thunder Bay
Thunder Bay1 stop$357
Toronto
Torontononstop$158
Ottawa
Ottawa1 stop$281
Thunder Bay
Thunder Bay1 stop$357

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

Recent round-trip flight deals from Chicago to Ontario

Wed, Sep 3 - Mon, Sep 8
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$158Porter Airlines
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Wed, Sep 3 - Sat, Sep 6
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$191Porter Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$215
Find Deal
Sat, Sep 27 - Sat, Oct 4
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$217
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
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Sat, Sep 27 - Sat, Oct 4
Delta Logo
6:15 pm - 11:29 pmMDW-YUL
4h 14m1 stop
Delta Logo
10:57 am - 5:35 pmYUL-MDW
7h 38m1 stop
$236Delta
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Wed, Sep 10 - Thu, Sep 18
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$247Air Transat
Find Deal
Fri, Sep 5 - Mon, Sep 8
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$249Air Transat
Find Deal
Thu, Sep 4 - Sat, Sep 6
WestJet Logo
10:31 am - 9:58 pmMDW-YYZ
10h 27m1 stop
WestJet Logo
7:45 am - 9:12 pmYYZ-MDW
14h 27m1 stop
$297WestJet
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Sat, Oct 25 - Sun, Oct 26
WestJet Logo
3:00 pm - 11:18 pmMDW-YYZ
7h 18m1 stop
WestJet Logo
6:20 am - 1:08 pmYYZ-MDW
7h 48m1 stop
$346WestJet
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 $148 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 $148.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $254 on average.

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.

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Good to know

Low seasonJanuary
Cheapest flight$61
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 26% 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 $277 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $86 one-way - $167 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 332 reviews
8.0Comfort
7.0Entertainment
8.7Crew
7.6Food
8.2Boarding
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.

All good the seats a little tight and no I pad screen

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.

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

Information on your arrival and departure airports

Chicago (MDW)

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