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Cheap flights from Toronto to Chicago from £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 22/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
30 Mar — 6 Apr1
1 adult

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in April or September, 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 25 March 2025.

Round-trip from

£163

One-way from

£104

Popular in

December

Cheapest in

April

Average price

£215

Good round-trip deal

£169 or less

Good one-way deal

£96 or less
Air Canada
  • Air Canada
  • 13/5-13/5
  • 2 total stops
  • 9h 31m total
  • Toronto to Chicago
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Delta
  • Delta
  • 22/4
  • 1 total stop
  • 8h 53m 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 March 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 25 March 2025.

Tue 13/508:10YYZ - ORD
2 stops7h 45mAir Canada
Tue 13/518:30ORD - YYZ
Nonstop1h 46mAir Canada
Deal found 24/3£163
Wed 30/417:59YYZ - ORD
1 stop3h 46mDelta
Wed 7/506:24ORD - YYZ
1 stop4h 16mDelta
Deal found 24/3£172
Wed 4/610:00YYZ - ORD
Nonstop1h 54mUnited Airlines
Thu 12/620:25ORD - YYZ
Nonstop1h 42mUnited Airlines
Deal found 24/3£176
Thu 24/412:20YYZ - ORD
Nonstop1h 55mMultiple Airlines
Sun 27/407:20ORD - YYZ
1 stop5h 19mMultiple Airlines
Deal found 24/3£179
Tue 13/507:25YTZ - ORD
1 stop5h 07mAir Canada
Tue 13/514:22ORD - YTZ
1 stop5h 15mAir Canada
Deal found 24/3£189
Thu 17/715:59YYZ - ORD
1 stop18h 23mWestJet
Sat 19/717:45ORD - YYZ
1 stop14h 08mWestJet
Deal found 25/3£233
Wed 23/416:45YYZ - ORD
1 stop14h 20mAlaska Airlines
Sat 26/417:56ORD - YYZ
1 stop20h 04mAlaska Airlines
Deal found 24/3£363
Sat 2/806:00YHM - ORD
2 stops16h 54mWestJet
Sat 9/809:30ORD - YHM
2 stops14h 11mWestJet
Deal found 24/3£1,288

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 25 March 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

Tue 13/5

08:10-14:55

2 stops7h 45m

Chicago O'Hare Intl

Tue 13/5

18:30-21:16

Nonstop1h 46m

£163

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 30/4

17:59-20:45

1 stop3h 46m

Chicago O'Hare Intl

Wed 7/5

06:24-11:40

1 stop4h 16m

£172

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 4/6

10:00-10:54

Nonstop1h 54m

Chicago O'Hare Intl

Thu 12/6

20:25-23:07

Nonstop1h 42m

£176

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 24/4

12:20-13:15

Nonstop1h 55m

Chicago O'Hare Intl

Sun 27/4

07:20-13:39

1 stop5h 19m

£179

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 13/5

07:25-11:32

1 stop5h 07m

Chicago O'Hare Intl

Tue 13/5

14:22-20:37

1 stop5h 15m

£189

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 17/7

15:59-09:22

1 stop18h 23m

Chicago O'Hare Intl

Sat 19/7

17:45-08:53

1 stop14h 08m

£233

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 23/4

16:45-06:05

1 stop14h 20m

Chicago O'Hare Intl

Wed 30/4

19:19-15:00

1 stop18h 41m

£363

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 2/8

06:00-21:54

2 stops16h 54m

Chicago O'Hare Intl

Sat 9/8

09:30-00:41

2 stops14h 11m

£1,288

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 22/4

14:30-22:23

1 stop8h 53m

£104

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 18/4

21:00-22:06

Nonstop2h 06m

£117

Flights are sorted by cheapest return flights first.

Deals found on 24/3

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 21 March 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 25 March 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 72% 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 25 March 2025.

The most flights from YTO to CHI are scheduled on a Monday (58 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (46 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 25 March 2025.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Alaska Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very Good
9,789 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very Good
9,789 reviews
Alaska Airlines
8.0
Very Good
9,789 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very Good
7,890 reviews
Alaska Airlines
8.0
Very Good
9,789 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,605 reviews
Alaska Airlines
8.0
Very Good
9,789 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very Good
9,789 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
WestJet
7.2
Good
2,785 reviews
Alaska Airlines
8.0
Very Good
9,789 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Air Canada is currently your cheapest option to Chicago, with prices starting at £163. Additional return tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at £172 and £176, respectively. Air Canada is 23% 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 Delta, with whom users have recently found tickets for as low as £104. However, be on the lookout for offers from United Airlines 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 Copa Airlines (88%), Emirates (87%) and ANA (86%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £81. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £166 on average our data indicates £223 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 25 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£169Average£268FlexibilityNo 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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