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Cheap flights from Chicago to Toronto from C$ 163

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Toronto departing on 14/11. 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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Cheap round-trip flights

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Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 260Air Transat
Find Deal
Mon, 9 Mar - Fri, 13 Mar
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 264Air Transat
Find Deal
Fri, 6 Mar - Sun, 8 Mar
Air Transat Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 285Air Transat
Find Deal
Fri, 20 Feb - Wed, 25 Feb
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
C$ 295Porter Airlines
Find Deal
Thu, 22 Jan - Thu, 29 Jan
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 312Porter Airlines
Find Deal
Mon, 9 Feb - Mon, 16 Feb
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
C$ 316Porter Airlines
Find Deal
Mon, 9 Feb - Sun, 15 Feb
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Multiple Airlines Logo
11:00 a.m. - 11:50 a.m.YTZ-MDW
1h 50mdirect
C$ 347Multiple Airlines
Find Deal
Sun, 22 Mar - Sat, 28 Mar
Air Canada Logo
7:05 a.m. - 2:55 p.m.ORD-YTZ
6h 50m1 stop
Air Canada Logo
3:30 p.m. - 8:00 p.m.YTZ-ORD
5h 30m1 stop
C$ 374Air Canada
Find Deal
Thu, 6 Nov - Sat, 8 Nov
Air Canada Logo
12:50 p.m. - 7:55 p.m.ORD-YTZ
6h 05m1 stop
Air Canada Logo
10:30 a.m. - 2:55 p.m.YTZ-ORD
5h 25m1 stop
C$ 381Air Canada
Find Deal
Sat, 29 Nov - Sat, 6 Dec
Multiple Airlines Logo
12:45 p.m. - 3:27 p.m.MDW-YTZ
1h 42mdirect
Multiple Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
C$ 385Multiple Airlines
Find Deal
Sat, 13 Dec - Sun, 11 Jan

Air Transat flights from Chicago to Toronto Island Airport

Our best Air Transat deals on Chicago to Toronto Island Airport flight tickets
Air Transat
9 Mar
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
13 Mar
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
C$ 260
Find similar
Air Transat
6 Mar
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
8 Mar
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
C$ 264
Find similar
Air Transat
20 Feb
MDW4:15 p.m.Chicago Midway
1h 42m
YTZ6:57 p.m.Toronto Island
25 Feb
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
C$ 285
Find similar

Porter Airlines flights from Chicago to Toronto Island Airport

Our best Porter Airlines deals on Chicago to Toronto Island Airport flight tickets
Porter Airlines
22 Jan
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
29 Jan
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
C$ 295
Find similar
Porter Airlines
9 Feb
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
16 Feb
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
C$ 312
Find similar
Porter Airlines
9 Feb
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
15 Feb
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
C$ 316
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Toronto Island 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 96,600 searches. Data last updated 16 October 2025.
Use the filters below to find and compare flights from Chicago to Toronto Island Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 9/3

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

Nonstop1h 42m

Toronto Island

Fri 13/3

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 260

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 6/3

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

Nonstop1h 42m

Toronto Island

Sun 8/3

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 264

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 20/2

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

Toronto Island

Wed 25/2

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 285

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 22/1

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

Nonstop1h 42m

Toronto Island

Thu 29/1

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

Nonstop1h 50m

C$ 295

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 9/2

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

Nonstop1h 42m

Toronto Island

Mon 16/2

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 312

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 9/2

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

Nonstop1h 42m

Toronto Island

Sun 15/2

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

Nonstop1h 50m

C$ 316

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 22/3

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

Nonstop1h 42m

Toronto Island

Sat 28/3

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

C$ 347

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Thu 6/11

7:05 a.m.-2:55 p.m.

1 stop6h 50m

Toronto Island

Sat 8/11

3:30 p.m.-8:00 p.m.

1 stop5h 30m

C$ 374

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sat 29/11

12:50 p.m.-7:55 p.m.

1 stop6h 05m

Toronto Island

Sat 6/12

10:30 a.m.-2:55 p.m.

1 stop5h 25m

C$ 381

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 13/12

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

Toronto Island

Sun 11/1

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

Nonstop1h 50m

C$ 385

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 Toronto from

How to get the cheapest flight ticket from Chicago to Toronto Island 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 typical price of a round-trip flight between Chicago and Toronto Island Airport?

What is the cheapest month to fly to Toronto Island Airport?

The cheapest month to fly to Toronto Island Airport from Chicago is in July. Flight prices, which tend to average around C$ 268, are often lower during this time because this is during the off-season. If you aren’t able to travel to Toronto Island Airport during the month of July, then flying in September is also cheap. Prices for this month can be found on momondo for an average of C$ 277.

What is the cheapest day to depart on your flight to Toronto Island Airport?

On average, the least expensive day to fly to Toronto Island Airport from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as C$ 311. However, this price may fluctuate depending on the airline, the season, and holidays. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 460. These prices are subject to change though, so be sure to set up a Price Alert for flights to Toronto Island Airport.

What is the cheapest time of day to depart on your flight to Toronto Island Airport?

Flying to Toronto Island Airport from Chicago in the morning is the least expensive time of day to depart. momondo users have found prices as low as C$ 361 when looking at flights departing in the morning. In contrast, the most expensive time of day to depart to Toronto Island Airport is at noon when prices are around C$ 476.

What is the cheapest Chicago to Toronto Island flight route?

Fly from Chicago Midway to Toronto Island for the best Chicago - Toronto Island flight prices

What cabin class options are available on Chicago to Toronto Island flights?

There is only 1 cabin class available to choose from on Chicago to Toronto Island 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 Chicago to Toronto Island Airport flights?

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

When to book flights from Chicago to Toronto Island Airport

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

Cheap Chicago to Toronto Island Airport (CHI to YTZ) flight deals and tips

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

Best price found

C$ 152

Fastest flight time

1h 42m

Direct flights

Every day
The best one-way flight to Toronto Island Airport from Chicago in the past 72 hours is C$ 152. The best round-trip flight deal from Chicago to Toronto Island Airport found on momondo in the last 72 hours is C$ 340.
The fastest flight from Chicago to Toronto Island Airport takes 1h 42m
Direct flights go from Chicago to Toronto Island Airport every day.
Search flight deals

  • How far is Chicago to Toronto Island by plane?

    There are 698.8 km between Chicago and Toronto Island. Flights usually cover this in 1h 42m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago to Toronto Island Airport are updated daily.

  • How old do you have to be to fly from Chicago to Toronto Island 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 Chicago to Toronto Island Airport.

  • What documentation or ID do you need to fly to Toronto Island Airport?

    The necessary travel and health documents for your Toronto Island 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 Chicago to Toronto Island Airport?

Travelling to a place near Toronto?

Book flights to Toronto if you plan to visit one of these locations
Apsley

Why use momondo?

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

It is quick and easy to find Chicago to Toronto 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 Toronto that suits you.

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

All flight searches from Chicago to Toronto on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Chicago and Toronto by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Chicago to Toronto flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Toronto Island Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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