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Cheap flights from Toronto to Chicago from £108

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 18/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
26 Feb — 5 Mar1
1 adult

The best prices from Toronto to Chicago are usually found in April or March, booked 77 days in advance, depart on a Monday or Sunday 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 21 February 2025.

Round-trip from

£175

One-way from

£108

Popular in

December

Cheapest in

April

Average price

£226

Good round-trip deal

£133 or less

Good one-way deal

£131 or less
United Airlines
  • United Airlines
  • 30/4-3/5
  • Nonstop
  • 3h 43m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 18/4
  • Nonstop
  • 2h 06m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (£8 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in February 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 21 February 2025.

Wed 30/417:30YYZ - ORD
Nonstop2h 00mUnited Airlines
Sat 3/518:01ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 21/2£175
Thu 13/321:00YYZ - ORD
Nonstop2h 06mMultiple Airlines
Thu 10/407:10ORD - YYZ
Nonstop1h 48mMultiple Airlines
Deal found 19/2£176
Fri 18/408:50YTZ - ORD
1 stop4h 13mAir Canada
Sat 19/407:20ORD - YTZ
1 stop6h 30mAir Canada
Deal found 20/2£188
Fri 18/421:00YYZ - ORD
Nonstop2h 06mAir Canada
Sat 19/416:00ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 20/2£192
Fri 18/409:45YYZ - ORD
1 stop7h 23mDelta
Sat 19/417:00ORD - YYZ
1 stop4h 55mDelta
Deal found 20/2£200
Wed 12/313:20YYZ - ORD
1 stop8h 24mWestJet
Fri 14/306:15ORD - YYZ
1 stop15h 44mWestJet
Deal found 19/2£242
Wed 12/311:30YYZ - ORD
Nonstop2h 00mAmerican Airlines
Fri 14/314:36ORD - YYZ
2 stops18h 14mAmerican Airlines
Deal found 20/2£282
Mon 10/300:40YYZ - ORD
1 stop18h 20mAustrian Airlines
Wed 9/418:05ORD - YYZ
1 stop19h 50mAustrian Airlines
Deal found 19/2£9,079

Find flights from Toronto to Chicago within your budget

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 21 February 2025.

Fly from

Toronto

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 30/4

14:45-15:51

Nonstop2h 06m

Chicago O'Hare Intl

Mon 5/5

13:00-15:46

Nonstop1h 46m

£175

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 13/3

21:00-22:06

Nonstop2h 06m

Chicago O'Hare Intl

Thu 10/4

07:10-09:58

Nonstop1h 48m

£176

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 18/4

08:50-12:03

1 stop4h 13m

Chicago O'Hare Intl

Sat 19/4

07:20-14:50

1 stop6h 30m

£188

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/4

21:00-22:06

Nonstop2h 06m

Chicago O'Hare Intl

Sat 19/4

13:56-21:27

1 stop6h 31m

£192

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/4

09:45-16:08

1 stop7h 23m

Chicago O'Hare Intl

Sat 19/4

17:00-22:55

1 stop4h 55m

£200

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/3

06:30-15:15

1 stop9h 45m

Chicago O'Hare Intl

Fri 14/3

06:15-23:30

2 stops16h 15m

£242

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/3

11:30-12:30

Nonstop2h 00m

Chicago O'Hare Intl

Fri 14/3

14:36-09:50

2 stops18h 14m

£282

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 10/3

00:40-18:00

1 stop18h 20m

Chicago O'Hare Intl

Wed 9/4

18:05-14:55

1 stop19h 50m

£9,079

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/4

21:00-22:06

Nonstop2h 06m

£108

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 24/3

08:50-12:56

1 stop5h 06m

£112

Flights are sorted by cheapest return flights first.

Deals found on 20/2

Showing 1-10 of 15 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.

Travel insights for flights from Toronto to Chicago

Get recent, data-driven insights about flights from Toronto to Chicago including ideal travel times, pricing trends, and more.

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 14 February 2025.

Booking 77 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 21 February 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 66% 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 21 February 2025.

The most flights from YTO to CHI are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 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 21 February 2025.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Delta, Austrian Airlines and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
8,212 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
8,212 reviews
Delta
8.0
Very Good
8,212 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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

Austrian Airlines
7.6
Good
773 reviews
Delta
8.0
Very Good
8,212 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
8,765 reviews
Delta
8.0
Very Good
8,212 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
8,212 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
2,801 reviews
Delta
8.0
Very Good
8,212 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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 £175. Additional return tickets that might be worth considering are offered by Air Canada and Delta, with the lowest prices starting at £188 and £200, respectively. United Airlines is 19% 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 £108. 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 Island - Chicago O'Hare Intl, Toronto Pearson Intl - 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 Emirates (90%), Republic Airways (89%) and ANA (84%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £130. While the most popular route (Toronto Island - Chicago O'Hare Intl) can be booked for £192 on average our data indicates £541 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 21 February 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£191Average£285FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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