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Cheap flights from Toronto Island Airport to Chicago from $151

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto Island Airport to Chicago departing on 3/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Toronto Island Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
Air Canada Logo
7:25 am - 10:06 am
ORD
-
YTZ
1h 41mnonstop
$229Air Canada
Fri, Jun 12 - Sun, Jun 14
Air Canada Logo
9:30 am - 2:53 pm
YTZ
-
ORD
6h 23m
1 stop
Air Canada Logo
7:25 am - 10:06 am
ORD
-
YTZ
1h 41mnonstop
$234Air Canada
Mon, Jun 1 - Fri, Jun 5
Air Canada Logo
12:15 pm - 1:10 pm
YTZ
-
ORD
1h 55mnonstop
Air Canada Logo
2:00 pm - 4:41 pm
ORD
-
YTZ
1h 41mnonstop
$253Air Canada
Wed, Jul 8 - Fri, Jul 10
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
Air Canada Logo
2:00 pm - 4:41 pm
ORD
-
YTZ
1h 41mnonstop
$258Air Canada
Thu, Jul 9 - Mon, Jul 13
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
Air Canada Logo
8:45 am - 3:51 pm
ORD
-
YTZ
6h 06m
1 stop
$261Air Canada
Wed, Jul 8 - Fri, Jul 10
Air Canada Logo
10:45 am - 2:55 pm
YTZ
-
ORD
5h 10m
1 stop
Air Canada Logo
11:05 am - 5:51 pm
ORD
-
YTZ
5h 46m
1 stop
$268Air Canada
Wed, Jul 8 - Fri, Jul 10
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
Air Canada Logo
2:00 pm - 4:41 pm
ORD
-
YTZ
1h 41mnonstop
$269Air Canada
Tue, Jul 28 - Thu, Jul 30
Multiple Airlines Logo
6:15 pm - 12:22 am
YTZ
-
ORD
7h 07m
1 stop
Multiple Airlines Logo
6:01 pm - 10:35 am
ORD
-
YTZ
15h 34m
1 stop
$275Multiple Airlines
Tue, Mar 17 - Wed, Mar 18
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
Air Canada Logo
7:25 am - 10:06 am
ORD
-
YTZ
1h 41mnonstop
$277Air Canada
Wed, Jul 1 - Sat, Jul 4
Multiple Airlines Logo
6:15 pm - 12:22 am
YTZ
-
ORD
7h 07m
1 stop
Multiple Airlines Logo
6:01 pm - 10:35 am
ORD
-
YTZ
15h 34m
1 stop
$280Multiple Airlines
Wed, Mar 25 - Thu, Mar 26

Air Canada flights from Toronto Island Airport to Chicago O'Hare Intl Airport

Our best Air Canada deals on Toronto Island Airport to Chicago O'Hare Intl Airport flight tickets
Air Canada
Jun 3
YTZ12:15 pmToronto Island
1h 55m
ORD1:10 pmChicago O'Hare Intl
Jun 5
ORD7:25 amChicago O'Hare Intl
1h 41m
YTZ10:06 amToronto Island
$200
Air Canada
Jun 12
YTZ7:20 pmToronto Island
1h 56m
ORD8:16 pmChicago O'Hare Intl
Jun 14
ORD7:25 amChicago O'Hare Intl
1h 41m
YTZ10:06 amToronto Island
$229
Air Canada
Jun 1
YTZ9:30 amToronto Island
6h 23m
1 stop
ORD2:53 pmChicago O'Hare Intl
Jun 5
ORD7:25 amChicago O'Hare Intl
1h 41m
YTZ10:06 amToronto Island
$234

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Island Airport to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 6/12

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 6/14

7:25 am-10:06 am

Nonstop1h 41m

$229

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 6/1

9:30 am-2:53 pm

1 stop6h 23m

Chicago O'Hare Intl

Fri 6/5

7:25 am-10:06 am

Nonstop1h 41m

$234

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 7/8

12:15 pm-1:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Fri 7/10

2:00 pm-4:41 pm

Nonstop1h 41m

$253

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 7/9

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Mon 7/13

2:00 pm-4:41 pm

Nonstop1h 41m

$258

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 7/8

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Fri 7/10

8:45 am-3:51 pm

1 stop6h 06m

$261

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 7/8

10:45 am-2:55 pm

1 stop5h 10m

Chicago O'Hare Intl

Fri 7/10

11:05 am-5:51 pm

1 stop5h 46m

$268

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 7/28

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Thu 7/30

2:00 pm-4:41 pm

Nonstop1h 41m

$269

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 3/17

6:15 pm-12:22 am

1 stop7h 07m

Chicago O'Hare Intl

Wed 3/18

6:01 pm-10:35 am

1 stop15h 34m

$275

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 7/1

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sat 7/4

7:25 am-10:06 am

Nonstop1h 41m

$277

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 3/25

6:15 pm-12:22 am

1 stop7h 07m

Chicago O'Hare Intl

Thu 3/26

6:01 pm-10:35 am

1 stop15h 34m

$280

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto Island Airport to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $459. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto Island Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $738.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Toronto Island Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $375 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $683. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Toronto Island to Chicago O'Hare Intl flight route?

Fly from Toronto Island to Chicago O'Hare Intl for the best Toronto Island - Chicago O'Hare Intl flight prices

What cabin class options are available on Toronto Island to Chicago O'Hare Intl flights?

There is only 1 cabin class available to choose from on Toronto Island to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto Island Airport to Chicago O'Hare Intl Airport flights?

You could potentially save up to 4% on your flight if you consider stops on a Toronto Island Airport to Chicago O'Hare Intl Airport flight.

When to book flights from Toronto Island Airport to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Island Airport to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Toronto Island Airport to Chicago O'Hare Intl Airport (YTZ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Island Airport to Chicago O'Hare Intl Airport

Best Price Found

$841

Fastest flight time

1h 56m

Direct flights

Every day
The best flight deal from Toronto Island Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $841
The fastest flight from Toronto Island Airport to Chicago O'Hare Intl Airport takes 1h 56m
Direct flights go from Toronto Island Airport to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Toronto Island to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 445.5 mi away from Toronto Island. 1h 56m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Toronto Island Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Toronto Island Airport to Chicago O'Hare Intl Airport refresh daily.

  • How old do you have to be to fly from Toronto Island Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Toronto Island Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Toronto Island Airport to Chicago O'Hare Intl Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Oak Brook
Joliet
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

It is quick and easy to find Toronto to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Toronto to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Toronto to Chicago.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Toronto to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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