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Cheap flights from Toronto to Chicago from £83

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 14/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
23 Jul — 30 Jul1
1 adult

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in June or April, booked 52 days in advance, depart on a Monday or Thursday and return on a Friday

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 18 July 2025.

Round-trip from

£119

One-way from

£83

Popular in

December

Cheapest in

June

Average price

£190

Good round-trip deal

£180 or less

Good one-way deal

£92 or less
United Airlines
  • United Airlines
  • 31/10-2/11
  • Nonstop
  • 3h 44m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 14/9
  • Nonstop
  • 1h 59m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (£12 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 July 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 18 July 2025.

Fri 31/1008:55YYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 2/1121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 16/7£119
Thu 4/907:30YYZ - ORD
1 stop5h 09mMultiple Airlines
Sun 7/920:25ORD - YYZ
Nonstop1h 43mMultiple Airlines
Deal found 16/7£140
Fri 3/1014:10YYZ - ORD
Nonstop1h 54mAir Canada
Mon 6/1018:20ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 18/7£148
Wed 10/917:00YYZ - ORD
1 stop6h 20mDelta
Fri 12/909:10ORD - YYZ
1 stop5h 12mDelta
Deal found 16/7£159
Sun 12/1015:25YTZ - ORD
1 stop5h 57mAir Canada
Sat 18/1008:40ORD - YTZ
1 stop5h 05mAir Canada
Deal found 16/7£167
Mon 25/806:00YYZ - ORD
1 stop17h 59mAmerican Airlines
Wed 27/809:50ORD - YYZ
1 stop4h 46mAmerican Airlines
Deal found 16/7£193
Thu 7/817:15YTZ - ORD
2 stops14h 49mMultiple Airlines
Wed 13/808:40ORD - YTZ
1 stop5h 06mMultiple Airlines
Deal found 17/7£245
Wed 23/706:00YHM - ORD
2 stops33h 13mMultiple Airlines
Fri 25/715:18ORD - YHM
3 stops32h 23mMultiple Airlines
Deal found 15/7£427

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 18 July 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

Fri 31/10

08:55-10:00

Nonstop2h 05m

Chicago O'Hare Intl

Sun 2/11

21:20-23:59

Nonstop1h 39m

£119

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/9

07:30-11:39

1 stop5h 09m

Chicago O'Hare Intl

Sun 7/9

20:25-23:08

Nonstop1h 43m

£140

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 3/10

14:10-15:04

Nonstop1h 54m

Chicago O'Hare Intl

Mon 6/10

18:20-21:02

Nonstop1h 42m

£148

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/9

17:00-22:20

1 stop6h 20m

Chicago O'Hare Intl

Fri 12/9

09:10-15:22

1 stop5h 12m

£159

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 12/10

15:25-20:22

1 stop5h 57m

Chicago O'Hare Intl

Sat 18/10

08:40-14:45

1 stop5h 05m

£167

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 25/8

06:00-22:59

1 stop17h 59m

Chicago O'Hare Intl

Wed 27/8

09:50-15:36

1 stop4h 46m

£193

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 7/8

17:15-07:04

2 stops14h 49m

Chicago O'Hare Intl

Wed 13/8

08:40-14:46

1 stop5h 06m

£245

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 14/9

07:00-07:59

Nonstop1h 59m

£83

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 16/8

06:20-15:02

1 stop9h 42m

£107

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 14/1

14:30-21:35

1 stop8h 05m

£125

Flights are sorted by cheapest return flights first.

Deals found on 16/7

Showing 1-10 of 11 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 July 2025.

Booking 52 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 18 July 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 65% 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 13 July 2025.

Travellers seeking maximum savings on their Toronto to Chicago flight should consider departing on Thursday 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 18 July 2025.

The most flights from YTO to CHI are scheduled on a Thursday (64 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 for a return flight from Toronto to Chicago?

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 18 July 2025.
Get a feel of what it's like to fly with Delta, United Airlines, andAmerican Airlines from Toronto to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
7,958 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very Good
7,958 reviews
Delta
8.0
Very Good
7,958 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,865 reviews
Delta
8.0
Very Good
7,958 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very Good
7,958 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,950 reviews
Delta
8.0
Very Good
7,958 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,744 reviews
Delta
8.0
Very Good
7,958 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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 £119. Additional return tickets that might be worth considering are offered by Air Canada and Delta, with the lowest prices starting at £148 and £159, respectively. United Airlines is 39% 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 £83. However, be on the lookout for offers from Delta and WestJet, 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 Cathay Pacific (100%), SkyWest Airlines (91%) and Egyptair (90%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £78. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £150 on average our data indicates £266 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

Browse thousands of different options on Cheapflights for your next trip

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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 18 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£138Average£199FlexibilityNo 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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