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.

$132 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 24 - Sun, Sep 27

10:45 am - 2:52 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

5h 07m1 stop Montreal Pierre Elliott Trudeau Intl

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

1h 42mnonstop

$206Air Canada

Fri, Oct 16 - Fri, Oct 23

12:15 pm - 1:25 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mnonstop

8:45 am - 3:50 pmORD Chicago O'Hare Intl-YTZ Toronto Island

6h 05m1 stop Montreal Pierre Elliott Trudeau Intl

$206Air Canada

Thu, Sep 24 - Sun, Sep 27

1:00 pm - 2:05 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

3:40 pm - 9:53 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 13m1 stop Montreal Pierre Elliott Trudeau Intl

$208Multiple Airlines

Tue, Oct 20 - Wed, Oct 21

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

2h 00mnonstop

11:05 am - 6:53 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

6h 48m1 stop Montreal Pierre Elliott Trudeau Intl

$208Multiple Airlines

Fri, Oct 30 - Tue, Nov 3

3:47 pm - 11:00 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

8h 13m1 stop Charlotte Douglas

9:42 am - 12:32 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mnonstop

$210American Airlines

Thu, Oct 1 - Sat, Oct 31

5:27 pm - 10:00 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 33m1 stop Washington, D.C. Reagan-National

11:45 am - 2:33 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 48mnonstop

$210American Airlines

Fri, Oct 2 - Mon, Oct 5

10:15 am - 11:21 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 06mnonstop

4:00 pm - 10:23 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

5h 23m1 stop Newark

$212United Airlines

Fri, Oct 2 - Mon, Oct 5

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

2h 00mnonstop

6:00 am - 11:43 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

4h 43m1 stop Newark

$212United Airlines

Mon, Nov 2 - Mon, Nov 9

10:35 am - 11:40 amYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

6:20 pm - 9:06 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mnonstop

$220Porter Airlines

Fri, Jan 8 - Mon, Jan 11

12:40 pm - 5:40 pmYUL Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl

6h 00m1 stop Toronto Island

12:20 pm - 7:05 pmORD Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl

5h 45m1 stop Toronto Island

$281Porter Airlines

Recent last minute flight deals from Ontario to Chicago

Wed, Sep 9 - Sun, Oct 11

5:15 pm - 6:18 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 03mnonstop

8:50 am - 11:49 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 59mnonstop

$313United Airlines

Wed, Sep 9 - Thu, Oct 15

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

2h 05mnonstop

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

1h 45mnonstop

$313United Airlines

Wed, Sep 9 - Sat, Oct 10

8:05 am - 9:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 55mnonstop

3:45 pm - 6:31 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$313Air Canada

Tue, Sep 8 - Sun, Oct 11

8:05 am - 9:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 55mnonstop

3:45 pm - 6:31 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 46mnonstop

$313Air Canada

Tue, Sep 8 - Sat, Oct 10

6:00 am - 12:59 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

7h 59m1 stop Detroit Metropolitan Wayne County

1:55 pm - 10:56 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

8h 01m1 stop Detroit Metropolitan Wayne County

$330Delta

Wed, Sep 9 - Sun, Oct 11

4:05 pm - 8:30 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

5h 25m1 stop Detroit Metropolitan Wayne County

7:00 am - 11:19 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

3h 19m1 stop Detroit Metropolitan Wayne County

$330Delta

Tue, Sep 8 - Sat, Sep 19

5:34 pm - 7:19 pmYUL Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl

2h 45mnonstop

6:29 am - 12:26 pmORD Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl

4h 57m1 stop Philadelphia

$350American Airlines

Wed, Sep 9 - Wed, Sep 16

12:31 pm - 2:11 pmYUL Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl

2h 40mnonstop

1:15 pm - 9:42 pmORD Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl

7h 27m1 stop Philadelphia

$350American Airlines

Thu, Sep 10 - Tue, Sep 15

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

2h 05mnonstop

11:42 am - 2:32 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 50mnonstop

$421Porter Airlines

Wed, Sep 9 - Sat, Sep 12

3:13 pm - 4:18 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

8:03 am - 10:59 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 56mnonstop

$482Porter Airlines

Recent direct flight deals from Ontario to Chicago

Fri, Oct 23 - Fri, Oct 30

12:15 pm - 1:25 pmYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mnonstop

7:25 am - 10:06 amORD Chicago O'Hare Intl-YTZ Toronto Island

1h 41mnonstop

$206Air Canada

Thu, Sep 24 - Sun, Sep 27

8:05 am - 9:00 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

1h 55mnonstop

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

1h 45mnonstop

$206Air Canada

Thu, Sep 24 - Sun, Sep 27

1:00 pm - 2:05 pmYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 05mnonstop

4:33 pm - 7:37 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

2h 04mnonstop

$212United Airlines

Wed, Sep 23 - Wed, Sep 23

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

$212United Airlines

Fri, Sep 25 - Sun, Sep 27

11:00 am - 12:00 pmYYZ 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

$212Multiple Airlines

Thu, Sep 24 - Sun, Sep 27

10:15 am - 11:21 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 06mnonstop

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

1h 45mnonstop

$212Multiple Airlines

Mon, Nov 2 - Mon, Nov 9

10:35 am - 11:40 amYTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mnonstop

6:20 pm - 9:06 pmORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mnonstop

$220Porter Airlines

Tue, Oct 27 - Wed, Oct 28

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

2h 05mnonstop

8:06 am - 10:59 amORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 53mnonstop

$223American Airlines

Wed, Oct 21 - Sun, Oct 25

7:29 am - 8:39 amYYZ Toronto Pearson Intl-ORD Chicago O'Hare Intl

2h 10mnonstop

9:46 am - 12:34 pmORD Chicago O'Hare Intl-YYZ Toronto Pearson Intl

1h 48mnonstop

$223American Airlines

Fri, Sep 18 - Sun, Sep 20

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

2h 05mnonstop

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

1h 50mnonstop

$326Porter Airlines

Useful Info

Low season	December
High season	August
Cheapest flight	$132

Best time to beat the crowds with an average 14% drop in price.

Most popular time to fly with an average 17% increase in price.

Flight from Toronto to Chicago O'Hare Airport

NicholFlew with United Airlines-Aug 2026

If you are a US citizen, make sure you allow enough time for customs in Toronto Pearson airport. My trip was really quick and smooth, but I've seen it at other times where it has been busier and needed more time.

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

Tinley Park

Hammond

Saint Joseph

Elk Grove Village

Des Plaines

Hoffman Estates

South Holland

Portage

Oakbrook Terrace

Willowbrook

Lansing

Delavan

Alsip

Northbrook

Lisle

Valparaiso

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$132 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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Cheapest flight

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

FAQs for booking Ontario to Chicago flights

Traveling to a place near Chicago?

More options for your flight to Chicago

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

Information on your arrival and departure airports

Cabin class types available on flights to Chicago

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Flights from domestic origins to Ontario

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