C$ 189 Find Cheap Flights from Ontario 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 to Chicago departing on 16/10. 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, 0 bags

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Flight Deals

Cheap Flights from Ontario to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Ontario 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Ontario to Chicago

Sat, 5 Sep - Mon, 7 Sep
Air Canada Logo
6:55 p.m. - 7:52 p.m.
YYZ
-
ORD
1h 57mdirect
Air Canada Logo
9:50 a.m. - 12:35 p.m.
ORD
-
YYZ
1h 45mdirect
C$ 288Air Canada
Mon, 29 Jun - Tue, 30 Jun
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 288Porter Airlines
Thu, 2 Jul - Sun, 5 Jul
Air Canada Logo
7:25 p.m. - 8:29 p.m.
YTZ
-
ORD
2h 04mdirect
Air Canada Logo
7:25 a.m. - 10:07 a.m.
ORD
-
YTZ
1h 42mdirect
C$ 288Air Canada
Wed, 9 Sep - Mon, 14 Sep
Multiple Airlines Logo
8:50 a.m. - 9:53 a.m.
YYZ
-
ORD
2h 03mdirect
Multiple Airlines Logo
3:45 p.m. - 6:30 p.m.
ORD
-
YYZ
1h 45mdirect
C$ 290Multiple Airlines
Thu, 2 Jul - Sun, 5 Jul
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 290Porter Airlines
Sat, 5 Sep - Tue, 8 Sep
Delta Logo
12:09 p.m. - 4:59 p.m.
YYZ
-
MDW
5h 50m
1 stop
Delta Logo
5:45 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 14m
1 stop
C$ 335Delta
Fri, 11 Sep - Sun, 13 Sep
Delta Logo
12:08 p.m. - 4:57 p.m.
YYZ
-
MDW
5h 49m
1 stop
Delta Logo
9:30 a.m. - 5:23 p.m.
MDW
-
YYZ
6h 53m
1 stop
C$ 336Delta
Thu, 3 Sep - Wed, 9 Sep
United Airlines Logo
9:45 a.m. - 11:21 a.m.
YUL
-
ORD
2h 36mdirect
United Airlines Logo
8:45 a.m. - 2:40 p.m.
ORD
-
YUL
4h 55m
1 stop
C$ 409United Airlines
Fri, 31 Jul - Tue, 4 Aug
American Airlines Logo
8:40 a.m. - 2:22 p.m.
YOW
-
ORD
6h 42m
1 stop
American Airlines Logo
2:38 p.m. - 9:35 p.m.
ORD
-
YOW
5h 57m
1 stop
C$ 536American Airlines
Wed, 21 Oct - Tue, 27 Oct
American Airlines Logo
8:40 a.m. - 2:05 p.m.
YOW
-
ORD
6h 25m
1 stop
American Airlines Logo
11:40 a.m. - 6:24 p.m.
ORD
-
YOW
5h 44m
1 stop
C$ 553American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flightC$ 189
Best time to beat the crowds but there is an average 48% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

Flights from Ontario to Chicago: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from Ontario to Chicago 
Learn how KAYAK collects reviews and tips from users.
BrianFlew with Air Canada
YYZ
-
ORD
Oct 2024
Be prepared for a labyrinthine experience traversing the various levels and passages of the Toronto airport. Bring quality walking shoes, as it is likely well over a km in total walking time.
Verified travelerFlew with United Airlines
YYZ
-
ORD
Mar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

FAQs for booking flights from Ontario to Chicago

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

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Ontario 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 Ontario up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Munster
Valparaiso
Benton Harbor
Hammond
Schererville
Portage
New Buffalo
Saint Joseph
Crown Point
Chesterton
Porter
Monticello

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Ontario

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom C$ 1,278
Business Class flights to Chicagofrom C$ 819
Premium Economy Class flights to Chicagofrom C$ 540
Economy Class flights to Chicagofrom C$ 272