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$ 146 CHEAP FLIGHTS from Ontario to Chicago

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

...and more

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Cheapest round-trip

C$ 247

Overall average: C$ 416

Multiple Airlines

Sun 25/1Wed 28/1

YYZ - ORD • 3 stops

Cheapest direct flights

C$ 247

Typical prices: C$ 368-C$ 508

United Airlines

Thu 29/1Sun 1/2

YYZ - ORD • Direct

Start a new search

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

We hope you love your trip to Chicago!

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

Sun, 25 Jan - Wed, 28 Jan

12:15 p.m. - 9:03 p.m.

YYZ

ORD

33h 48m3 stops

7:20 a.m. - 11:20 p.m.

ORD

YYZ

15h 00m1 stop

C$ 247Multiple Airlines

Fri, 20 Feb - Mon, 23 Feb

9:15 a.m. - 10:05 a.m.

YTZ

MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.

MDW

YTZ

1h 42mdirect

C$ 247Porter Airlines

Thu, 29 Jan - Sun, 1 Feb

9:00 a.m. - 2:55 p.m.

YYZ

ORD

6h 55m1 stop

8:40 p.m. - 11:19 p.m.

ORD

YYZ

1h 39mdirect

C$ 250Air Canada

Sun, 25 Jan - Wed, 28 Jan

12:15 p.m. - 7:38 p.m.

YYZ

ORD

32h 23m3 stops

5:32 p.m. - 2:20 p.m.

ORD

YYZ

19h 48m2 stops

C$ 251Multiple Airlines

Fri, 6 Feb - Sun, 8 Feb

10:30 a.m. - 5:42 p.m.

YYZ

ORD

8h 12m1 stop

6:00 a.m. - 11:59 a.m.

ORD

YYZ

4h 59m1 stop

C$ 254American Airlines

Fri, 13 Feb - Sun, 15 Feb

4:50 p.m. - 5:48 p.m.

YYZ

ORD

1h 58mdirect

2:00 p.m. - 4:39 p.m.

ORD

YYZ

1h 39mdirect

C$ 255Air Canada

Thu, 29 Jan - Sun, 1 Feb

3:30 p.m. - 4:40 p.m.

YYZ

ORD

2h 10mdirect

6:28 p.m. - 9:21 p.m.

ORD

YYZ

1h 53mdirect

C$ 263Lufthansa

Sat, 14 Feb - Tue, 17 Feb

7:30 a.m. - 12:07 p.m.

YUL

ORD

5h 37m1 stop

11:51 a.m. - 3:10 p.m.

ORD

YUL

2h 19mdirect

C$ 280American Airlines

Thu, 5 Feb - Sun, 8 Feb

7:45 a.m. - 12:46 p.m.

YYZ

MDW

6h 01m1 stop

1:26 p.m. - 7:08 p.m.

MDW

YYZ

4h 42m1 stop

C$ 292Delta

Thu, 5 Feb - Sun, 8 Feb

7:45 a.m. - 12:46 p.m.

YYZ

MDW

6h 01m1 stop

1:26 p.m. - 7:08 p.m.

MDW

YYZ

4h 42m1 stop

C$ 294Delta

Useful Info

Low season	January
High season	August
Cheapest flight	C$ 146

Best time to beat the crowds but there is an average 2% increase in price.

Most popular time to fly and prices are also 2% lower on average.

Flight from Ottawa to Chicago O'Hare Airport

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

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

Benton Harbor

New Buffalo

Merrillville

Portage

Schererville

Hammond

Crown Point

Saint Joseph

Chesterton

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$ 1,073

Business Class flights to Chicagofrom C$ 952

Prem Econ Class flights to Chicagofrom C$ 532

Economy Class flights to Chicagofrom C$ 177

C$ 146 Find Cheap Flights from Ontario to Chicago

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

Everything you should know

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