Question 1

What are the cheapest airlines flying from Toronto to Chicago round-trip?

Accepted Answer

Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at £120. Additional return tickets that might be worth considering are offered by Air Canada and American Airlines, with the lowest prices starting at £130 and £150, respectively. United Airlines is 38% cheaper than the average price of flights available within the next 90 days to this destination.

Question 2

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

Accepted Answer

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as £79. However, be on the lookout for offers from Air Canada and American Airlines, as they are both options that can get you from Toronto to Chicago for a low price.

Question 3

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

Accepted Answer

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.

Question 4

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

Accepted Answer

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.

Question 5

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

Accepted Answer

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.

Question 6

Weekly flight availability from Toronto to Chicago

Accepted Answer

The most flights from YTO to CHI are scheduled on a Wednesday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).

Question 7

E

Accepted Answer

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.

Question 8

E

Accepted Answer

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).

Question 9

What are the most popular routes from Toronto to Chicago?

Accepted Answer

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.

Question 10

What are the cheapest flights from Toronto to Chicago?

Accepted Answer

Looking at all options, your cheapest flight can be booked for £112. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £136 on average our data indicates £175 when flying from Toronto to Chicago.

Question 11

What are the most reliable airlines from Toronto to Chicago?

Accepted Answer

The top 3 most reliable airlines when flying from Toronto to Chicago are Cathay Pacific (100%), Copa Airlines (93%) and Egyptair (92%).

Question 12

What is the cheapest day to fly round-trip from Toronto to Chicago?

Accepted Answer

Leaving on a Sunday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 237% on the overall cost on flights from Toronto to Chicago.

Question 13

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

Accepted Answer

To save on the cost of your flight from Toronto to Chicago, book at least 53 days before your planned departure. Booking around this time can save you about 119% on the cost of this flight compared to booking a flight leaving this week. We have found prices from £217 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as £360.

Question 14

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

Accepted Answer

Our data shows that April tends to be the cheapest month to fly to Chicago from Toronto. Users have commonly found prices around £195 for the month, but tickets can be as low as £125. Due to multiple factors, prepare for potentially higher prices in December.

Question 15

What is the cheapest time of day to fly from YTO to CHI?

Accepted Answer

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 64% versus a flight at midday.

Question 16

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

Accepted Answer

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

Question 17

How can I find direct flights from Toronto to Chicago?

Accepted Answer

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

Question 18

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

Accepted Answer

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.

Question 19

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

Accepted Answer

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.

Question 20

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

Accepted Answer

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.

Question 21

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

Accepted Answer

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.

Question 22

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

Accepted Answer

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.

Round-trip from	£120
One-way from	£79
Popular in	December
Cheapest in	April
Average price	£185
Good round-trip deal	£195 or less
Good one-way deal	£134 or less

Cheap flights from Toronto to Chicago from £79

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 23/7. Fares are subject to change and may not be available on all flights or dates of travel.

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

Cheap flight deals from Toronto to Chicago

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Cheapest flights from Toronto to ChicagoExplore 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 7월 2025.

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 7월 2025.

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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.

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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 27 June 2025.

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

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 7월 2025.

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 29 June 2025.

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 7월 2025.

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 4 7월 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.

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?

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

What are the most popular routes from Toronto to Chicago?

What are the most reliable airlines from Toronto to Chicago?

What are the cheapest flights from Toronto to Chicago?

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

How can I find direct flights from Toronto to Chicago?

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

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Toronto to Chicago

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Top airline flying from Toronto to Chicago

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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?

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

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

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

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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 7월 2025.