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$ 159 CHEAP FLIGHTS from Ontario to Chicago

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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.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Ontario to Chicago

Mon, 20 Oct - Thu, 23 Oct

4:00 p.m. - 11:44 p.m.YYZ-ORD

8h 44m1 stop

12:53 p.m. - 9:07 p.m.ORD-YYZ

7h 14m1 stop

C$ 271

Find Deal

Mon, 20 Oct - Thu, 23 Oct

4:00 p.m. - 11:44 p.m.YYZ-ORD

8h 44m1 stop

12:53 p.m. - 9:07 p.m.ORD-YYZ

7h 14m1 stop

C$ 273

Find Deal

Thu, 23 Oct - Mon, 27 Oct

6:00 a.m. - 4:43 p.m.YKF-ORD

11h 43m1 stop

2:20 p.m. - 5:28 a.m.ORD-YKF

14h 08m1 stop

C$ 287WestJet

Find Deal

Thu, 23 Oct - Mon, 27 Oct

6:00 a.m. - 4:43 p.m.YKF-ORD

11h 43m1 stop

2:20 p.m. - 5:28 a.m.ORD-YKF

14h 08m1 stop

C$ 309WestJet

Find Deal

Fri, 17 Oct - Mon, 20 Oct

1:10 p.m. - 4:24 p.m.YUL-MDW

4h 14m1 stop

9:35 a.m. - 4:00 p.m.MDW-YUL

5h 25m1 stop

C$ 325Porter Airlines

Find Deal

Thu, 16 Oct - Sun, 19 Oct

10:45 a.m. - 4:24 p.m.YUL-MDW

6h 39m1 stop

5:20 p.m. - 10:15 p.m.MDW-YUL

3h 55m1 stop

C$ 327Porter Airlines

Find Deal

Wed, 29 Oct - Wed, 5 Nov

6:15 p.m. - 8:00 p.m.YUL-ORD

2h 45mdirect

7:15 a.m. - 10:20 a.m.ORD-YUL

2h 05mdirect

C$ 334Air Canada

Find Deal

Wed, 29 Oct - Wed, 5 Nov

9:10 a.m. - 1:01 p.m.YUL-ORD

4h 51m1 stop

12:50 p.m. - 3:57 p.m.ORD-YUL

2h 07mdirect

C$ 345Air Canada

Find Deal

Sat, 4 Oct - Tue, 7 Oct

9:45 a.m. - 11:23 a.m.YUL-ORD

2h 38mdirect

7:11 a.m. - 10:40 a.m.ORD-YUL

2h 29mdirect

C$ 360United Airlines

Find Deal

Sat, 4 Oct - Sun, 5 Oct

9:45 a.m. - 11:23 a.m.YUL-ORD

2h 38mdirect

2:08 p.m. - 5:26 p.m.ORD-YUL

2h 18mdirect

C$ 363United Airlines

Find Deal

Cheapest round-trip

C$ 271

Typical prices: C$ 357-497

Multiple Airlines

Mon 20/10Thu 23/10

YYZ - ORD • 1 stop

Cheapest direct flights

C$ 332

Typical prices: C$ 325-399

Porter Airlines

Sat 18/10Sat 25/10

YTZ - MDW • Direct

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KAYAK searches hundreds of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

Useful Info

Low season	January
High season	August
Cheapest flight	C$ 159

Best time to beat the crowds but there is an average 4% increase in price.

Most popular time to fly and prices are also 1% lower on average.

Flight from Toronto Region of Waterloo Intl to Chicago

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.

Munster

New Buffalo

Portage

Merrillville

Benton Harbor

Schererville

Crown Point

Hammond

Chesterton

Saint Joseph

Valparaiso

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

Cabin class types available on flights to Ontario

First Class flights to Chicagofrom C$ 1,798

Business Class flights to Chicagofrom C$ 880

Prem Econ Class flights to Chicagofrom C$ 534

Economy Class flights to Chicagofrom C$ 237

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

C$ 159 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

Everything you should know

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