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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

C$ 135 CHEAP FLIGHTS from Ontario to Chicago

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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.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Ontario to Chicago

Fri, 19 Sep - Sun, 21 Sep

12:20 p.m. - 1:14 p.m.YYZ-ORD

1h 54mdirect

3:50 p.m. - 6:33 p.m.ORD-YYZ

1h 43mdirect

C$ 201Air Canada

Find Deal

Fri, 5 Sep - Mon, 8 Sep

6:40 p.m. - 8:11 p.m.YUL-ORD

2h 31mdirect

10:40 a.m. - 1:54 p.m.ORD-YUL

2h 14mdirect

C$ 205Air Canada

Find Deal

Mon, 25 Aug - Fri, 12 Sep

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

5:20 p.m. - 8:02 p.m.MDW-YTZ

1h 42mdirect

C$ 211Porter Airlines

Find Deal

Thu, 3 Jul - Mon, 7 Jul

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

9:40 a.m. - 12:20 p.m.MDW-YTZ

1h 40mdirect

C$ 212Porter Airlines

Find Deal

Fri, 19 Sep - Mon, 22 Sep

7:00 a.m. - 7:59 a.m.YYZ-ORD

1h 59mdirect

9:31 p.m. - 10:04 a.m.ORD-YYZ

11h 33m1 stop

C$ 215United Airlines

Find Deal

Thu, 4 Sep - Wed, 10 Sep

2:30 p.m. - 7:48 p.m.YYZ-ORD

6h 18m1 stop

7:15 a.m. - 1:47 p.m.ORD-YYZ

5h 32m1 stop

C$ 235United Airlines

Find Deal

Sat, 30 Aug - Fri, 12 Sep

7:55 a.m. - 8:45 a.m.YTZ-MDW

1h 50mdirect

9:15 a.m. - 11:57 a.m.MDW-YTZ

1h 42mdirect

C$ 254Air Transat

Find Deal

Tue, 30 Sep - Thu, 2 Oct

5:15 p.m. - 6:50 p.m.YUL-ORD

2h 35mdirect

9:48 a.m. - 3:21 p.m.ORD-YUL

4h 33m1 stop

C$ 257American Airlines

Find Deal

Thu, 26 Jun - Mon, 30 Jun

7:55 a.m. - 8:45 a.m.YTZ-MDW

1h 50mdirect

9:40 a.m. - 12:20 p.m.MDW-YTZ

1h 40mdirect

C$ 261Air Transat

Find Deal

Tue, 30 Sep - Thu, 2 Oct

3:45 p.m. - 8:27 p.m.YYZ-ORD

5h 42m1 stop

9:48 a.m. - 5:15 p.m.ORD-YYZ

6h 27m1 stop

C$ 261American Airlines

Find Deal

Useful Info

Low season	January
High season	August
Cheapest flight	C$ 135

Best time to beat the crowds but there is an average 1% increase in price.

Most popular time to fly and prices are also 0% lower on average.

Flight from Toronto Pearson Airport to Chicago O'Hare Airport

BrianFlew with Air CanadaYYZ-ORDOct 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 AirlinesYYZ-ORDMar 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

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.

Portage

Benton Harbor

New Buffalo

Merrillville

Schererville

Munster

Saint Joseph

Valparaiso

Hammond

Chesterton

Monticello

Porter

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Ontario

First Class flights to Chicagofrom C$ 1,183

Business Class flights to Chicagofrom C$ 930

Prem Econ Class flights to Chicagofrom C$ 528

Economy Class flights to Chicagofrom C$ 204

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

C$ 135 Find Cheap Flights from Ontario to Chicago

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

Cheap Flights from Ontario to Chicago

Recent round-trip flight deals from Ontario to Chicago

Recent one-way flight deals from Ontario to Chicago

Recent last minute flight deals from Ontario to Chicago

Recent direct flight deals from Ontario to Chicago

Good to know

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

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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Ontario

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight