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.

$133 CHEAP FLIGHTS from Ontario to Chicago (ORD)

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Flight Deals

Cheap Flights from Ontario to Chicago

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

Thu, Sep 10 - Sun, Sep 13

6:50 pm - 7:48 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 58mnonstop

8:40 pm - 11:26 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$199Air Canada

Thu, Sep 10 - Sun, Sep 13

2:00 pm - 2:55 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 55mnonstop

8:40 pm - 11:26 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$200Air Canada

Fri, Nov 6 - Mon, Nov 9

4:35 pm - 5:30 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

1h 55mnonstop

6:10 pm - 8:50 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 40mnonstop

$204Porter Airlines

Sat, Sep 12 - Thu, Sep 17

11:40 am - 12:45 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

2:51 pm - 5:44 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 53mnonstop

$208Porter Airlines

Sun, Sep 6 - Tue, Sep 8

11:00 am - 12:00 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

9:18 pm - 11:59 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 41mnonstop

$211United Airlines

Sun, Sep 20 - Thu, Sep 24

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

7:09 am - 9:54 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$211United Airlines

Tue, Sep 15 - Wed, Sep 23

6:30 am - 7:40 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

5:48 pm - 11:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 58m1 stop Philadelphia

$217British Airways

Sat, Sep 12 - Thu, Sep 17

8:50 am - 9:53 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mnonstop

11:05 am - 6:12 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

6h 07m1 stop Montreal Pierre Elliott Trudeau Intl

$218Multiple Airlines

Tue, Sep 8 - Fri, Sep 11

1:15 pm - 2:20 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

5:48 pm - 11:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 58m1 stop Philadelphia

$221American Airlines

Fri, Sep 25 - Mon, Sep 28

1:15 pm - 2:20 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

4:00 pm - 11:46 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

6h 46m1 stop Philadelphia

$221American Airlines

Recent last minute flight deals from Ontario to Chicago

Tue, Aug 11 - Sun, Sep 13

7:35 pm - 8:41 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 06mnonstop

7:25 am - 10:07 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$332Air Canada

Thu, Aug 13 - Sat, Aug 22

7:35 pm - 8:41 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 06mnonstop

7:25 am - 10:18 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 53mnonstop

$344Air Canada

Tue, Aug 11 - Sun, Sep 13

9:00 pm - 10:05 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

10:43 am - 1:42 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 59mnonstop

$353United Airlines

Tue, Aug 11 - Sun, Sep 13

3:00 pm - 10:15 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

8h 15m1 stop Newark

5:53 pm - 8:44 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 51mnonstop

$359United Airlines

Thu, Aug 13 - Fri, Aug 28

9:45 am - 4:17 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

7h 32m1 stop Detroit Metropolitan Wayne County

8:48 am - 5:24 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

7h 36m1 stop Detroit Metropolitan Wayne County

$374Delta

Thu, Aug 13 - Thu, Aug 27

9:45 am - 4:17 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

7h 32m1 stop Detroit Metropolitan Wayne County

8:48 am - 5:24 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

7h 36m1 stop Detroit Metropolitan Wayne County

$374Delta

Wed, Aug 12 - Wed, Aug 19

11:39 am - 12:44 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

8:09 am - 10:59 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mnonstop

$382American Airlines

Wed, Aug 12 - Wed, Aug 19

11:39 am - 12:44 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

7:30 am - 2:58 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

6h 28m1 stop Charlotte Douglas

$392American Airlines

Wed, Aug 12 - Thu, Aug 20

7:20 am - 8:30 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

9:45 am - 12:33 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 48mnonstop

$479Porter Airlines

Tue, Aug 11 - Thu, Aug 13

11:39 am - 12:44 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

8:32 pm - 11:29 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 57mnonstop

$486Porter Airlines

Recent direct flight deals from Ontario to Chicago

Thu, Sep 10 - Sun, Sep 13

6:50 pm - 7:48 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 58mnonstop

8:40 pm - 11:26 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$199Air Canada

Wed, Sep 16 - Mon, Sep 21

7:35 pm - 8:41 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 06mnonstop

7:25 am - 10:07 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 42mnonstop

$200Air Canada

Fri, Nov 6 - Mon, Nov 9

4:35 pm - 5:30 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

1h 55mnonstop

6:10 pm - 8:50 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 40mnonstop

$204Porter Airlines

Sat, Sep 12 - Thu, Sep 17

11:40 am - 12:45 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

2:51 pm - 5:44 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 53mnonstop

$208Porter Airlines

Sun, Sep 6 - Tue, Sep 8

11:00 am - 12:00 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

9:18 pm - 11:59 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 41mnonstop

$211United Airlines

Sun, Sep 20 - Thu, Sep 24

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

7:09 am - 9:54 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$211United Airlines

Sat, Sep 19 - Mon, Sep 21

8:50 am - 9:53 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mnonstop

2:15 pm - 5:01 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$238Multiple Airlines

Fri, Sep 4 - Tue, Sep 8

7:00 am - 8:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 00mnonstop

9:55 am - 12:40 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 45mnonstop

$238Multiple Airlines

Sun, Sep 13 - Wed, Sep 16

6:30 am - 7:40 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

9:45 am - 12:35 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mnonstop

$275American Airlines

Tue, Nov 17 - Tue, Nov 24

12:10 pm - 2:15 pmYUL Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

8:08 am - 11:26 amORD Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl

2h 18mnonstop

$296American Airlines

Useful Info

Low season	December
High season	September
Cheapest flight	$133

Best time to beat the crowds with an average 9% drop in price.

Most popular time to fly and prices are also 31% lower on average.

Flight from Toronto Pearson Airport to Chicago O'Hare Airport

BrianFlew with Air Canada-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-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.

Gurnee

Merrillville

South Haven

Oak Brook

Saint Joseph

Tinley Park

Hammond

Elk Grove Village

Des Plaines

Hoffman Estates

Portage

South Holland

Willowbrook

Lansing

Delavan

Alsip

Northbrook

Lisle

Elmhurst

Valparaiso

Everything you need to know for your flight to Chicago

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Chicago (ORD)

$133 Find Cheap Flights from Ontario to Chicago - Compare and Save

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

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

FAQs for booking Ontario to Chicago flights

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

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

Find direct flights for Chicago

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Flights from domestic origins to Ontario

Choose which airport to fly into in Chicago