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$70+ Cheap flights from Chicago (CHI) to Toronto (YTO)

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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTO
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Toronto are usually found in August or June, booked 86 days in advance, depart on a Friday or Thursday 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 July 18, 2025.

Round-trip from

$177
(Mytrip)

One-way from

$75
(United Airlines)

Popular in

November

Cheapest in

August

Average price

$269

Good round-trip deal

$189 or less

Good one-way deal

$72 or less
From Chicago (CHI) to Toronto (YTO)
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One-way flight from Chicago (CHI) to Toronto (YTO)
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Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 18, 2025.

This Flightnetwork deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:25 pmORD - YYZ
Nonstop1h 43mAir Canada
Sun 9/78:15 amYYZ - ORD
Nonstop1h 53mAir Canada
Deal found 7/15$174
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:02 amORD - YYZ
1 stop6h 41mUnited Airlines
Tue 11/116:52 amYYZ - ORD
Nonstop2h 06mUnited Airlines
Deal found 7/16$177
This Gotogate deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 9/77:30 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 7/16$190
This Mytrip deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/98:40 amORD - YTZ
1 stop5h 05mAir Canada
Sat 9/133:25 pmYTZ - ORD
1 stop5h 46mAir Canada
Deal found 7/17$204
This Mytrip deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Sat 9/137:30 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
Deal found 7/17$209
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/56:12 amORD - YYZ
1 stop9h 22mAmerican Airlines
Wed 8/135:59 pmYYZ - ORD
1 stop5h 50mAmerican Airlines
Deal found 7/14$214
This United deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/411:40 amORD - YYZ
1 stop4h 39mMultiple Airlines
Sun 9/78:15 amYYZ - ORD
Nonstop1h 53mMultiple Airlines
Deal found 7/15$232
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/99:30 amMDW - YYZ
1 stop3h 02mDelta
Sat 9/1312:14 pmYYZ - MDW
1 stop7h 21mDelta
Deal found 7/17$234
This lastminute.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/49:15 amMDW - YYZ
1 stop13h 18mWestJet
Sun 9/71:20 pmYYZ - MDW
1 stop21h 14mWestJet
Deal found 7/16$281
This oojo deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:30 pmORD - YHM
1 stop30h 10mWestJet
Mon 10/66:00 amYHM - ORD
1 stop11h 43mWestJet
Deal found 7/15$313
This Mytrip deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/235:16 pmORD - YTZ
3 stops22h 30mMultiple Airlines
Sat 8/303:25 pmYTZ - ORD
1 stop5h 51mMultiple Airlines
Deal found 7/17$313
This Mytrip deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/67:08 amORD - YHM
2 stops16h 33mMultiple Airlines
Fri 8/86:00 amYHM - ORD
3 stops25h 03mMultiple Airlines
Deal found 7/15$399

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 2,558,603 searches. Data last updated July 18, 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

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 9/4

8:25 pm-11:08 pm

Nonstop1h 43m

Toronto Pearson Intl

Sun 9/7

8:15 am-9:08 am

Nonstop1h 53m

$174

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 11/6

6:02 am-1:43 pm

1 stop6h 41m

Toronto Pearson Intl

Tue 11/11

6:52 am-7:58 am

Nonstop2h 06m

$177

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/4

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Sun 9/7

7:30 am-8:19 am

Nonstop1h 49m

$190

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Tue 9/9

8:40 am-2:45 pm

1 stop5h 05m

Toronto Island

Sat 9/13

3:25 pm-8:11 pm

1 stop5h 46m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 9/9

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Sat 9/13

7:30 am-8:19 am

Nonstop1h 49m

$209

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 8/5

6:12 am-4:34 pm

1 stop9h 22m

Toronto Pearson Intl

Wed 8/13

5:59 pm-10:49 pm

1 stop5h 50m

$214

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 9/4

11:40 am-5:19 pm

1 stop4h 39m

Toronto Pearson Intl

Sun 9/7

8:15 am-9:08 am

Nonstop1h 53m

$232

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 9/9

9:30 am-1:32 pm

1 stop3h 02m

Toronto Pearson Intl

Sat 9/13

12:14 pm-6:35 pm

1 stop7h 21m

$234

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 9/4

9:15 am-11:33 pm

1 stop13h 18m

Toronto Pearson Intl

Sun 9/7

1:20 pm-9:34 am

1 stop21h 14m

$281

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

Thu 10/2

5:30 pm-12:40 am

1 stop30h 10m

Hamilton

Mon 10/6

6:00 am-4:43 pm

1 stop11h 43m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

Showing 1-10 of 28 results
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The best insider tips for Chicago to Toronto flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Toronto trip
Airlines
Air Canada

Economy Latitude offers priority check-in and two checked bags, ideal for efficient travel.


Air Canada provides high-speed Wi-Fi on most flights, book in advance for best rates.

Read more about Air Canadaby Jessica Macdonald
United Airlines

United's Economy Plus offers extra legroom seats, enhancing comfort for short flights.


United Polaris offers lie-flat seats and upscale amenities, perfect for premium travel.

Read more about United Airlinesby Harriet Baskas
Airports
ORD

For a quick departure, use the 'L' train from downtown Chicago to ORD, avoiding traffic delays common with taxis or rideshares.

Read more about ORDby Ramsey Qubein
YYZ

For a budget-friendly arrival, use public transportation from YYZ to downtown Toronto, despite needing a connection.

Read more about YYZby Kaitlyn McInnis
Our travel experts
Jessica Macdonald

Jessica Macdonald

Expert on Air Canada

Jessica Macdonald

Jessica Macdonald

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYZ

Kaitlyn McInnis

Kaitlyn McInnis

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more

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 July 11, 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 $243). Flying from Chicago to Toronto in July is currently the most expensive (average of $350). 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 July 18, 2025.

It’s optimal to fly from Chicago to Toronto in the morning. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the afternoon.

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 July 13, 2025.

Travelers seeking maximum savings on their Chicago to Toronto flight should consider departing on Friday mornings when fares are most often at their lowest. Saturday afternoons 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 July 18, 2025.

The most flights from CHI to YTO are scheduled on a Wednesday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 on average).

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 July 18, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, and Air Transat from Chicago to Toronto. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
311 reviews

Food

7.6

Crew

8.7

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
Porter Airlines
8.0
Very good
311 reviews
Porter Airlines
8.0
Very good
311 reviews

Food

7.6

Crew

8.7

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
Delta
8.0
Very good
7,959 reviews
Porter Airlines
8.0
Very good
311 reviews

Food

7.6

Crew

8.7

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
Air Transat
7.7
Good
416 reviews
Porter Airlines
8.0
Very good
311 reviews

Food

7.6

Crew

8.7

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
United Airlines
7.4
Good
8,864 reviews
Porter Airlines
8.0
Very good
311 reviews

Food

7.6

Crew

8.7

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
311 reviews

Food

7.6

Crew

8.7

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make

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.

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

    Flying on Air Canada is currently your cheapest option to Toronto, with prices starting at $177. Additional round-trip tickets that might be worth considering are offered by United Airlines and Porter Airlines, with the lowest prices starting at $186 and $190, respectively. You may be able to fly from Chicago to Toronto for 39% less than the average price by searching for these airlines.

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

    One-way options have recently been found by users for as low as $75 on United Airlines. Other airlines that offer cheap prices include Air Canada from $77 and Porter Airlines from $84 one-way.

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

    While some choose either Chicago Midway - Toronto Island or Chicago Midway - Toronto Pearson Intl, Chicago O'Hare Intl - Toronto Pearson Intl is the most popular route from Chicago to Toronto.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Toronto consider choosing SkyWest Airlines (91%), Envoy Air (84%) or Japan Airlines (80%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Toronto?

    While on average a flight from Chicago to Toronto is generally $1,538, our data shows the cheapest flight currently is $69. When looking at the most popular route, (Chicago O'Hare Intl - Toronto Pearson Intl), you can expect to pay $168 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 $243). Flying from Chicago to Toronto in July is currently the most expensive (average of $350). 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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Alternative routes for Chicago to Toronto

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
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Evansville to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Kingston flights
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Top 4 airlines flying from Chicago to Toronto

Discover the top 4 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 2,558,603 searches. Data last updated July 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$109Average$295FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$119Average$370FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$143Average$324FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$199Average$376FlexibilityNo cancel feeOn-time71%

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