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Cheap flights from Chicago to Toronto from C$ 104

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 30/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTO
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Chicago to Toronto are usually found in July or June, booked 86 days in advance, depart on a Saturday or Tuesday and return on a Friday

Cheap flight deals from Chicago to Toronto

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Toronto (YTO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 11 September 2025.

Round-trip from

C$ 237

One-way from

C$ 104

Popular in

January

Cheapest in

July

Average price

C$ 382

Good round-trip deal

C$ 266 or less

Good one-way deal

C$ 125 or less
Porter Airlines
  • Porter Airlines
  • 2/10-5/10
  • Nonstop
  • 3h 31m total
  • Chicago to Toronto
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Porter Airlines
  • Porter Airlines
  • 30/9
  • Nonstop
  • 1h 42m total
  • Chicago to Toronto
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Highest demand for flights based on searches. 8% potential increase in price (C$ 53 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Toronto (YTO).
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Price to beat on a one-way flight from Chicago (CHI) to Toronto (YTO).
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Find flight deals from Chicago to Toronto

Cheapest flights from Chicago to Toronto
Explore the most affordable flight options available from Chicago to Toronto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 11 September 2025.

Thu 2/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 237
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 238
Wed 15/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 18/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 241
Thu 23/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 26/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/9C$ 245
Wed 29/104:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 5/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 8/9C$ 248
Wed 26/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 30/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/9C$ 254
Tue 30/99:55 a.m.ORD - YYZ
Nonstop1h 42mAir Canada
Thu 2/108:15 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
Deal found 9/9C$ 262
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 7/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 263
Sat 4/1010:40 a.m.ORD - YYZ
1 stop5h 44mAir Canada
Sun 5/106:15 a.m.YYZ - ORD
1 stop4h 36mAir Canada
Deal found 9/9C$ 269
Sat 11/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 14/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 270
Mon 20/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Thu 23/106:30 a.m.YYZ - ORD
1 stop10h 34mMultiple Airlines
Deal found 9/9C$ 272
Fri 26/96:44 p.m.ORD - YYZ
1 stop18h 21mMultiple Airlines
Tue 30/96:30 a.m.YYZ - ORD
1 stop12h 09mMultiple Airlines
Deal found 9/9C$ 276

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Toronto 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, Cheapflights users made 629,999 searches. Data last updated 11 September 2025.
Use the filters below to find and compare flights from Chicago to Toronto that are best for you.

Fly from

Chicago

Fly to

Toronto

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 8/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 237

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 22/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 5/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Tue 7/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 22/11

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

Nonstop1h 42m

Toronto Island

Mon 24/11

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

Nonstop1h 50m

C$ 270

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 14/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Wed 15/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 270

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 8/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 285

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 26/2

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

Nonstop1h 42m

Toronto Island

Fri 27/2

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

Nonstop1h 50m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Toronto

Have a flexible travel schedule? Discover the best time to fly to Toronto from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Toronto

How far ahead should I book a flight from Chicago to Toronto?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Toronto. Price data was last updated on 29 August 2025.

The price you pay for your flight from Chicago to Toronto may vary depending on when you book. For the best chance of a lower fare, look to book 86 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Toronto?

Currently, January is the cheapest month in which you can book a flight from Chicago to Toronto (average of C$ 168). Flying from Chicago to Toronto in July is currently the most expensive (average of C$ 258). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YTO?

Find hourly flight availability from Chicago to Toronto. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 11 September 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Toronto in the evening. If you’re flexible enough to do this you can expect to save up to 31% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chicago to Toronto?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Toronto. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Chicago to Toronto flight should consider departing on Monday evenings when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Toronto

Explore weekly flight availability from Chicago to Toronto. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 11 September 2025.

The most flights from CHI to YTO are scheduled on a Thursday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 on average).

How much does it cost to fly round-trip from Chicago to Toronto?

Reviews of airlines servicing Toronto

Get insights into the airlines that provide service to Toronto. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Toronto. Reviews last updated 11 September 2025.
Read through reviews of airlines operating flights from Chicago to Toronto, such as Porter Airlines,United Airlines, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,937 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Toronto. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Toronto?

    Porter Airlines, Air Canada, and United Airlines can get you from Chicago to Toronto in just under 1h 42m. Your travel time can differ by up to 10h 02m. Chicago and Toronto are separated by a distance of 711 km. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Toronto round-trip?

    Our cheapest airline available from Chicago to Toronto is Air Canada. Our recent data shows that you can find tickets from as low as C$ 204 on this airline. An additional option worth looking into is United Airlines, starting at C$ 261. You may be able to fly from Chicago to Toronto for 48% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Toronto one-way?

    For one-way options, check prices for Porter Airlines. According to our data, you can fly for as low as C$ 104. Users have also found prices from C$ 108 and C$ 118 on Air Canada and United Airlines, respectively.

  • What are the most popular routes from Chicago to Toronto?

    The most popular route from Chicago to Toronto is Chicago O'Hare Intl - Toronto Pearson Intl. You may also consider Chicago Midway - Toronto Island or Chicago Midway - Toronto Pearson Intl.

  • What are the most reliable airlines from Chicago to Toronto?

    The top 3 most reliable airlines when flying from Chicago to Toronto are Qatar Airways (85%), Envoy Air (80%) and SkyWest Airlines (80%).

  • What are the cheapest flights from Chicago to Toronto?

    While on average a flight from Chicago to Toronto is generally C$ 472, our data shows the cheapest flight currently is C$ 124. When looking at the most popular route, (Chicago O'Hare Intl - Toronto Pearson Intl), you can expect to pay C$ 280 for that flight.

  • Can I find deals for flights from Chicago to Toronto that include hotel bookings?

    Yes. In addition to deals on Chicago to Toronto flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Toronto?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Toronto.

  • Can I find deals for business class flights from Chicago to Toronto?

    Yes. Cheapflights offers flight deals from Chicago to Toronto by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Toronto?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Toronto (average of C$ 168). Flying from Chicago to Toronto in July is currently the most expensive (average of C$ 258). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 2 airlines flying from Chicago to Toronto

Discover the top 2 airlines that operate flights from Chicago to Toronto. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 204AverageC$ 412FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 261AverageC$ 357FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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How does Cheapflights help users find flights from Chicago to Toronto?

Deals for Chicago to Toronto flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

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It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Toronto.

Can Cheapflights find flights from Chicago to Toronto with no change fees?

Yes, we can. To see specific flights from Chicago to Toronto with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Chicago to Toronto become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Toronto from Chicago today and book when prices fit your budget.

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