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Cheap flights from Toronto Island Airport to Chicago from $122

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 6/18. 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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0 bags

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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 Transat Logo
1:40 pm - 2:35 pm
YTZ
-
ORD
1h 55mnonstop
Air Transat Logo
11:45 am - 2:25 pm
ORD
-
YTZ
1h 40mnonstop
$198Air Transat
Thu, Sep 3 - Sun, Sep 6
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
$199Air Canada
Thu, Sep 17 - Sun, Sep 20
Air Canada Logo
6:50 am - 10:53 am
YTZ
-
ORD
5h 03m
1 stop
Air Canada Logo
8:45 am - 3:52 pm
ORD
-
YTZ
6h 07m
1 stop
$204Air Canada
Sat, Apr 25 - Wed, May 6
Air Canada Logo
6:50 am - 10:53 am
YTZ
-
ORD
5h 03m
1 stop
Air Canada Logo
12:50 pm - 7:52 pm
ORD
-
YTZ
6h 02m
1 stop
$205Air Canada
Tue, Apr 21 - Sat, Apr 25
Air Transat Logo
8:40 pm - 9:35 pm
YTZ
-
ORD
1h 55mnonstop
Air Transat Logo
11:45 am - 2:25 pm
ORD
-
YTZ
1h 40mnonstop
$206Air Transat
Fri, Sep 18 - Mon, Sep 21
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
$207Air Canada
Wed, Jul 1 - Sun, Jul 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
$208Air Canada
Thu, Jul 9 - Mon, Jul 13
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
$210Air Canada
Sat, Jul 25 - Wed, Jul 29
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
Air Canada Logo
11:05 am - 5:51 pm
ORD
-
YTZ
5h 46m
1 stop
$211Air Canada
Thu, Jul 9 - Mon, Jul 13
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
$212Air Canada
Fri, Jun 26 - Mon, Jun 29

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
Sep 17
YTZ7:20 pmToronto Island
1h 56m
ORD8:16 pmChicago O'Hare Intl
Sep 20
ORD7:25 amChicago O'Hare Intl
1h 41m
YTZ10:06 amToronto Island
$199
Air Canada
Apr 25
YTZ6:50 amToronto Island
5h 03m
1 stop
ORD10:53 amChicago O'Hare Intl
May 6
ORD8:45 amChicago O'Hare Intl
6h 07m
1 stop
YTZ3:52 pmToronto Island
$204
Air Canada
Apr 21
YTZ6:50 amToronto Island
5h 03m
1 stop
ORD10:53 amChicago O'Hare Intl
Apr 25
ORD12:50 pmChicago O'Hare Intl
6h 02m
1 stop
YTZ7:52 pmToronto Island
$205

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

Our best Air Transat deals on Toronto Island Airport to Chicago O'Hare Intl Airport flight tickets
Air Transat
Sep 3
YTZ1:40 pmToronto Island
1h 55m
ORD2:35 pmChicago O'Hare Intl
Sep 6
ORD11:45 amChicago O'Hare Intl
1h 40m
YTZ2:25 pmToronto Island
$198
Air Transat
Sep 18
YTZ8:40 pmToronto Island
1h 55m
ORD9:35 pmChicago O'Hare Intl
Sep 21
ORD11:45 amChicago O'Hare Intl
1h 40m
YTZ2:25 pmToronto Island
$206

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 April 5, 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

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 9/3

1:40 pm-2:35 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 9/6

11:45 am-2:25 pm

Nonstop1h 40m

$198

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 9/17

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 9/20

7:25 am-10:06 am

Nonstop1h 41m

$199

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/25

6:50 am-10:53 am

1 stop5h 03m

Chicago O'Hare Intl

Wed 5/6

8:45 am-3:52 pm

1 stop6h 07m

$204

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 4/21

6:50 am-10:53 am

1 stop5h 03m

Chicago O'Hare Intl

Sat 4/25

12:50 pm-7:52 pm

1 stop6h 02m

$205

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 9/18

8:40 pm-9:35 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 9/21

11:45 am-2:25 pm

Nonstop1h 40m

$206

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 7/1

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 7/5

7:25 am-10:06 am

Nonstop1h 41m

$207

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 7/9

12:15 pm-1:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 7/13

2:00 pm-4:41 pm

Nonstop1h 41m

$208

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 7/25

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Wed 7/29

7:25 am-10:06 am

Nonstop1h 41m

$210

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 7/9

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Mon 7/13

11:05 am-5:51 pm

1 stop5h 46m

$211

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 6/26

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Mon 6/29

7:25 am-10:06 am

Nonstop1h 41m

$212

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 $470. 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 $741.

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 $699. 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?

No. A direct flight is the cheapest option for a flight between Toronto Island Airport to Chicago O'Hare Intl Airport.

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

$128

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Toronto Island Airport in the past 72 hours is $128. The best round-trip flight deal from Toronto Island Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $189.
The fastest flight from Toronto Island Airport to Chicago O'Hare Intl Airport takes 1h 55m
Direct flights go from Toronto Island Airport to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Toronto Island Airport to Chicago O'Hare Intl Airport

  • 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 55m 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
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Janesville
Aurora
Racine
Hammond
Elgin
Tinley Park
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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