C$ 155 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 28/5. 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

Fri, 8 May - Sun, 10 May
Porter Airlines Logo
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 a.m. - 6:15 p.m.
MDW
-
YUL
6h 50m
1 stop
C$ 222Porter Airlines
Fri, 8 May - Sun, 10 May
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 252Porter Airlines
Fri, 8 May - Sun, 10 May
Air Canada Logo
5:00 a.m. - 9:05 a.m.
YUL
-
ORD
5h 05m
1 stop
Air Canada Logo
9:55 a.m. - 5:26 p.m.
ORD
-
YUL
6h 31m
1 stop
C$ 263Air Canada
Fri, 5 Jun - Mon, 8 Jun
Air Canada Logo
4:30 p.m. - 8:16 p.m.
YUL
-
ORD
4h 46m
1 stop
Air Canada Logo
7:25 a.m. - 1:45 p.m.
ORD
-
YUL
5h 20m
1 stop
C$ 264Air Canada
Tue, 7 Apr - Tue, 14 Apr
Multiple Airlines Logo
9:25 a.m. - 10:15 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 292Multiple Airlines
Mon, 13 Apr - Tue, 14 Apr
Multiple Airlines Logo
11:40 a.m. - 12:22 a.m.
YTZ
-
ORD
13h 42m
2 stops
Multiple Airlines Logo
6:01 p.m. - 10:25 a.m.
ORD
-
YTZ
15h 24m
1 stop
C$ 329Multiple Airlines
Sun, 24 May - Tue, 2 Jun
Delta Logo
2:20 p.m. - 6:33 p.m.
YYZ
-
MDW
5h 13m
1 stop
Delta Logo
9:22 a.m. - 1:30 p.m.
MDW
-
YYZ
3h 08m
1 stop
C$ 375Delta
Sat, 4 Apr - Tue, 7 Apr
Delta Logo
6:20 a.m. - 8:53 a.m.
YYZ
-
MDW
3h 33m
1 stop
Delta Logo
9:30 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 29m
1 stop
C$ 390Delta
Thu, 4 Jun - Sun, 7 Jun
WestJet Logo
8:40 p.m. - 4:40 p.m.
YKF
-
ORD
21h 00m
1 stop
WestJet Logo
5:30 p.m. - 7:50 p.m.
ORD
-
YKF
25h 20m
1 stop
C$ 1,016WestJet
Thu, 4 Jun - Sun, 7 Jun
WestJet Logo
8:40 p.m. - 4:40 p.m.
YKF
-
ORD
21h 00m
1 stop
WestJet Logo
5:30 p.m. - 7:50 p.m.
ORD
-
YKF
25h 20m
1 stop
C$ 1,031WestJet
Useful Info

Good to know

Low seasonJanuary
Cheapest flightC$ 155
Best time to beat the crowds but there is an average 57% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Montreal to Chicago Midway 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
Munster
Merrillville
Benton Harbor
Valparaiso
Portage
Hammond
Schererville
New Buffalo
Crown Point
Saint Joseph
Chesterton
Monticello
Porter

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$ 2,862
Business Class flights to Chicagofrom C$ 360
Premium Economy Class flights to Chicagofrom C$ 529
Economy Class flights to Chicagofrom C$ 223