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Cheap flights from Toronto to Chicago from £103

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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
21 Apr — 28 Apr1
1 adult

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in April or March, booked 81 days in advance, depart on a Monday or Tuesday and return on a Sunday

Cheap flight deals from Toronto to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Chicago (CHI). 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 16 April 2025.

Round-trip from

£152

One-way from

£103

Popular in

December

Cheapest in

April

Average price

£188

Good round-trip deal

£165 or less

Good one-way deal

£207 or less
Air Canada
  • Air Canada
  • 10/5-18/5
  • Nonstop
  • 3h 51m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 4/8
  • Nonstop
  • 1h 54m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (£7 potential increase over avg. return price).
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Cheapest flight prices on average. 0% potential price decrease (£2 potential savings vs. average return price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
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Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).
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Find flight deals from Toronto to Chicago

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 16 April 2025.

Sat 10/512:00YYZ - ORD
Nonstop1h 55mMultiple Airlines
Sun 18/516:41ORD - YYZ
Nonstop1h 56mMultiple Airlines
Deal found 15/4£152
Wed 7/514:10YYZ - ORD
Nonstop1h 55mUnited Airlines
Sun 11/518:01ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 15/4£155
Thu 8/508:50YTZ - ORD
1 stop4h 13mAir Canada
Sat 10/508:40ORD - YTZ
1 stop7h 10mAir Canada
Deal found 15/4£166
Thu 8/516:30YYZ - ORD
Nonstop1h 54mAir Canada
Sat 10/513:55ORD - YYZ
1 stop6h 44mAir Canada
Deal found 15/4£172
Tue 6/512:54YYZ - ORD
1 stop5h 10mDelta
Tue 13/511:05ORD - YYZ
1 stop5h 10mDelta
Deal found 15/4£178
Sun 15/619:15YYZ - ORD
2 stops16h 01mAmerican Airlines
Tue 17/608:35ORD - YYZ
2 stops8h 59mAmerican Airlines
Deal found 15/4£229
Sat 17/511:30YYZ - ORD
1 stop8h 18mWestJet
Mon 19/519:25ORD - YYZ
1 stop12h 33mWestJet
Deal found 15/4£239
Wed 21/519:30YTZ - ORD
1 stop12h 57mMultiple Airlines
Fri 23/521:08ORD - YTZ
1 stop15h 32mMultiple Airlines
Deal found 15/4£271
Tue 15/706:00YHM - ORD
1 stop11h 44mWestJet
Thu 17/706:00ORD - YHM
2 stops17h 41mWestJet
Deal found 15/4£1,005

Cheapflights Fare Finder

Customise your flight search to find flights from Toronto to Chicago 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 858,174 searches. Data last updated 16 April 2025.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Toronto

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 10/5

12:00-12:55

Nonstop1h 55m

Chicago O'Hare Intl

Sun 18/5

16:41-19:37

Nonstop1h 56m

£152

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 7/5

14:10-15:05

Nonstop1h 55m

Chicago O'Hare Intl

Sun 11/5

18:01-20:44

Nonstop1h 43m

£155

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 8/5

08:50-12:03

1 stop4h 13m

Chicago O'Hare Intl

Sat 10/5

08:40-16:50

1 stop7h 10m

£166

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 8/5

16:30-17:24

Nonstop1h 54m

Chicago O'Hare Intl

Sat 10/5

13:55-21:39

1 stop6h 44m

£172

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 6/5

12:54-17:04

1 stop5h 10m

Chicago O'Hare Intl

Tue 13/5

11:05-17:15

1 stop5h 10m

£178

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 15/6

19:15-10:16

2 stops16h 01m

Chicago O'Hare Intl

Tue 17/6

08:35-18:34

2 stops8h 59m

£229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 17/5

11:30-18:48

1 stop8h 18m

Chicago O'Hare Intl

Mon 19/5

19:25-08:58

1 stop12h 33m

£239

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 21/5

19:30-07:27

1 stop12h 57m

Chicago O'Hare Intl

Fri 23/5

21:08-13:40

1 stop15h 32m

£271

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Tue 15/7

06:00-16:44

1 stop11h 44m

Chicago O'Hare Intl

Thu 17/7

06:00-00:41

2 stops17h 41m

£1,005

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 4/8

14:20-15:14

Nonstop1h 54m

£103

Flights are sorted by cheapest return flights first.

Deals found on 14/4

Showing 1-10 of 14 results
1
2

Best time to book a flight from Toronto to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto with our price prediction graph.
Estimated return 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 Toronto to Chicago

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

Use this chart to determine the optimal time to book a return flight from Toronto to Chicago. Price data was last updated on 11 April 2025.

Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of £595). Flying from Toronto to Chicago in July is currently the most expensive (average of £843). 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 YTO to CHI?

Find hourly flight availability from Toronto to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 16 April 2025.

When flying from Toronto to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 68% versus a flight at midday.

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

Use this chart to determine the cheapest time to fly return from Toronto to Chicago. Price data was last updated on 16 February 2025.

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

Weekly flight availability from Toronto to Chicago

Explore weekly flight availability from Toronto to Chicago. 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 16 April 2025.

The most flights from YTO to CHI are scheduled on a Wednesday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 16 April 2025.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Delta, United Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
7,917 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very Good
7,917 reviews
Delta
8.0
Very Good
7,917 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,658 reviews
Delta
8.0
Very Good
7,917 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very Good
7,917 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,806 reviews
Delta
8.0
Very Good
7,917 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
9,134 reviews
Delta
8.0
Very Good
7,917 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Toronto to Chicago. 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 Toronto to Chicago round-trip?

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at £155. Additional return tickets that might be worth considering are offered by Air Canada and Delta, with the lowest prices starting at £166 and £178, respectively. United Airlines is 25% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as £103. However, be on the lookout for offers from Air Canada and Delta, as they are both options that can get you from Toronto to Chicago for a low price.

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

    Most travelers choose Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago O'Hare Intl or Hamilton - Chicago O'Hare Intl when deciding on the best route from Toronto to Chicago.

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

    The top 3 most reliable airlines when flying from Toronto to Chicago are Copa Airlines (88%), Egyptair (87%) and Emirates (85%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £79. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £172 on average our data indicates £227 when flying from Toronto to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto to Chicago 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 Toronto to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of £595). Flying from Toronto to Chicago in July is currently the most expensive (average of £843). 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 Toronto to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights

Top airline flying from Toronto to Chicago

Discover the top airline that operate flights from Toronto to Chicago. 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 858,174 searches. Data last updated 16 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£162Average£262FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Toronto to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Toronto to Chicago?

Cheapflights simply makes it quick and affordable to book flights from Toronto to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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

Certainly. Search results for flights to Chicago from Toronto shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Yes! Start tracking prices for Toronto to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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