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Cheap flights from Toronto to Chicago from £111

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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
9 Nov — 16 Nov1
1 adult

The best prices from Toronto to Chicago are usually found in April or February, booked 87 days in advance, depart on a Thursday or Friday and return on a Monday

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 930,449 searches. Data last updated 4 November 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 29/11

15:30-16:29

Nonstop1h 59m

£111

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 11/2

15:00-22:55

1 stop8h 55m

£112

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 6/1

14:30-19:59

1 stop6h 29m

£122

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/12

10:00-22:14

2 stops13h 14m

£148

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 16/11

14:05-23:00

2 stops9h 55m

£178

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 11/2

15:50-09:55

2 stops19h 05m

£135

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 16/11

12:25-18:41

1 stop7h 16m

£685

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 16/11

05:00-08:57

1 stop4h 57m

£703

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 28/11

21:00-22:07

Nonstop2h 07m

Chicago O'Hare Intl

Thu 5/12

07:19-09:58

Nonstop1h 39m

£184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 25/11

07:20-11:53

1 stop5h 33m

Chicago O'Hare Intl

Mon 2/12

07:28-12:46

1 stop4h 18m

£200

Flights are sorted by cheapest first

Deals found on 4/11

Showing 1-10 of 14 results
1
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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 4 November 2024.

Round-trip from

£184

One-way from

£111

Popular in

November

Cheapest in

April
United Airlines
  • United Airlines
  • 28/11-5/12
  • Nonstop
  • 3h 46m total
  • Toronto to Chicago
Search Deals
United Airlines
  • United Airlines
  • 4/12
  • Nonstop
  • 2h 07m total
  • Toronto to Chicago
Search Deals
High demand for flights, 12% potential price rise
Search Deals
Best time to find cheap flights, 10% potential price drop
Search Deals

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 4 November 2024.

Thu 28/1121:00YYZ - ORD
Nonstop2h 07mUnited Airlines
Thu 5/1207:19ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 4/11£184
Mon 25/1107:20YYZ - ORD
1 stop5h 33mMultiple Airlines
Mon 2/1207:28ORD - YYZ
1 stop4h 18mMultiple Airlines
Deal found 4/11£200
Fri 13/1206:30YYZ - ORD
1 stop9h 13mDelta
Mon 16/1215:35ORD - YYZ
1 stop6h 59mDelta
Deal found 4/11£207
Thu 5/1206:30YYZ - ORD
1 stop16h 44mWestJet
Fri 6/1212:25ORD - YYZ
2 stops16h 54mWestJet
Deal found 3/11£248
Wed 18/1200:30YYZ - ORD
1 stop8h 33mAir Canada
Thu 26/1207:20ORD - YYZ
1 stop5h 21mAir Canada
Deal found 4/11£483

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 1 November 2024.

Booking 87 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.

Find deals

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 £601). Flying from Toronto to Chicago in July is currently the most expensive (average of £774). 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 4 November 2024.

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 afternoon, which can drop the price by up to 4% versus a flight in the morning.

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 4 November 2024.

The most flights from YTO to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 4 November 2024.
Read through reviews of airlines operating flights from Toronto to Chicago, such as United Airlines, Delta and WestJet. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
8,829 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 10

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

Delta
8.0
Very Good
8,829 reviews
Delta
8.0
Very Good
8,829 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 10

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

Austrian Airlines
7.6
Good
818 reviews
Delta
8.0
Very Good
8,829 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 10

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

United Airlines
7.4
Good
9,226 reviews
Delta
8.0
Very Good
8,829 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 10

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

WestJet
7.3
Good
2,803 reviews
Delta
8.0
Very Good
8,829 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 10

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

Air Canada
7.0
Good
8,123 reviews
Delta
8.0
Very Good
8,829 reviews
Check prices

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 10

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 £184. Additional return tickets that might be worth considering are offered by Delta and WestJet, with the lowest prices starting at £207 and £248, respectively. United Airlines is 10% 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 £111. 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 Egyptair (100%), Jazz (100%) and Lufthansa (100%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £121. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £302 on average our data indicates £422 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 £601). Flying from Toronto to Chicago in July is currently the most expensive (average of £774). 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 930,449 searches. Data last updated 4 November 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£186Average£277FlexibilityNo 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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