How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are round-trip flights from Toronto to Chicago?

The best price we found for a round-trip flight from Toronto to Chicago is C$262. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Toronto to Chicago?

1 hour and 50 minutes is the average flight time from Toronto to Chicago.

Which airlines fly direct from Toronto to Chicago?

American Airlines, United and Alaska Airlines fly direct from Toronto to Chicago.

How many flights are there a week from Toronto to Chicago?

There are 491 flights per week flying from Toronto to Chicago, as of April 2024.

When is the cheapest time to fly from Toronto to Chicago?

The cheapest month to fly from Toronto to Chicago is usually May.

What's the cheapest airport to fly to in Chicago?

If you're flying from Toronto, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from C$262 .

Which upcoming date is cheapest to fly from Toronto to Chicago on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Toronto to Chicago on Monday, May 13, 2024 .

Can I get a direct flight from Toronto to Chicago?

Yes – the average flight time is 1 hour and 50 minutes.

How can I get the best flight deal from Toronto to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly with from Toronto to Chicago?

The cheapest airline that flies to Chicago is Flair Airlines, and the cheapest airline that flies to Chicago O'Hare International Airport is Porter Airlines (Canada) Ltd.

Cheap flights from Toronto to Chicago from C$262

Compare Toronto to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Toronto to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Toronto to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Chicago.C$262 per passenger.Departing Mon, May 13, returning Wed, May 15.Round-trip flight with Flair Airlines and Spirit Airlines.Outbound indirect flight with Flair Airlines, departing from Toronto Pearson International on Mon, May 13, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Wed, May 15, arriving in Toronto Pearson International.Price includes taxes and charges.From C$262, select.

Chicago.C$301 per passenger.Departing Tue, Jun 4, returning Tue, Jun 11.Round-trip flight with Flair Airlines and Spirit Airlines.Outbound indirect flight with Flair Airlines, departing from Toronto Pearson International on Tue, Jun 4, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Tue, Jun 11, arriving in Toronto Pearson International.Price includes taxes and charges.From C$301, select.

Chicago.C$311 per passenger.Departing Thu, May 23, returning Mon, May 27.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Thu, May 23, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Mon, May 27, arriving in Toronto Island.Price includes taxes and charges.From C$311, select.

Chicago.C$313 per passenger.Departing Wed, Jun 5, returning Sat, Jun 8.Round-trip flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departing from Toronto Island on Wed, Jun 5, arriving in Chicago Midway.Inbound direct flight with Porter Airlines (Canada) Ltd departing from Chicago Midway on Sat, Jun 8, arriving in Toronto Island.Price includes taxes and charges.From C$313, select.

Stay one step ahead. Find the best value travel with the latest deals, tips and news.

Find the cheapest month to fly from Toronto to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Toronto to Chicago flights are currently cheapest in May.

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Direct flights from Toronto to Chicago

Alternative Toronto to Chicago routes

Looking for the cheapest, fastest or easiest route from Toronto to Chicago? You could fly into the following airports instead.

Toronto to Chicago: Flight information

The things to know before you go.

Cheapest flight found	C$262
Cheapest month to fly	May
Average flight time	1 hr, 50 mins
Most popular airline	American Airlines
Average flights per week	491

Finding cheap flights from Toronto to Chicago: Frequently asked questions

: There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
: The best price we found for a round-trip flight from Toronto to Chicago is C$262. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
: 1 hour and 50 minutes is the average flight time from Toronto to Chicago.
: American Airlines, United and Alaska Airlines fly direct from Toronto to Chicago.
: There are 491 flights per week flying from Toronto to Chicago, as of April 2024.
: The cheapest month to fly from Toronto to Chicago is usually May.
: If you're flying from Toronto, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from C$262.
: After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Toronto to Chicago on Monday, May 13, 2024.
: Yes – the average flight time is 1 hour and 50 minutes.
: We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
: We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
: In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
: The cheapest airline that flies to Chicago is Flair Airlines, and the cheapest airline that flies to Chicago O'Hare International Airport is Porter Airlines (Canada) Ltd.

Top tips for finding a cheap flight from Toronto to Chicago

Finding cheap tickets from Toronto to Chicago is easy with a little flexibility. Use our Whole Month search feature to scan through the calendar for the cheapest dates. You can also set up a Price Alert for your route and let us monitor the fares for you, sending notifications when prices change. If you’d rather skip layovers, select the Direct Flights search to view non-stop options that’ll save you time.

Booking your tickets early often leads to savings, but we can also find you some last-minute deals. In general, December is the best time to schedule your trip from Toronto to Chicago, with the lowest average fares across the board. Keep these strategies in mind to find the best itinerary.

Handy information about Toronto airport

Toronto offers a range of airports catering to different travel needs, from regional flights to international destinations. Waterloo International Airport operates from a single terminal and handles both domestic and seasonal international flights. Those departing from Waterloo have access primarily via car or rideshare options. Buttonville Municipal Airport serves general aviation and flight training with its single terminal and is reached by similar ground transport methods.

Billy Bishop Toronto City Airport, situated on the city’s waterfront, is unique for its pedestrian tunnel link to the mainland and lends itself to business and regional travellers with its focus on short-haul flights. Toronto Pearson International Airport, the largest in Toronto, features two terminals connected by an automated mover and boasts a wealth of transport links, including public transit. Pearson accommodates a sweeping range of airlines and flights from domestic to international. Lastly, John C. Munro Hamilton International Airport, also with a single terminal, is accessible via car or rideshare and is known to serve domestic and some international flights, appealing to leisure and low-cost travellers.

Chicago airport: good to know

Chicago hosts multiple airports, each with its own specific role in serving the needs of travellers. Chicago Executive Airport operates with a single terminal, facilitating ground transportation through rental cars, taxis, limousines, and ride-sharing services, focusing mainly on private and corporate aircraft.

DuPage Airport, similar in structure with one terminal, shares a focus on general aviation, offering similar ground transport options. Chicago Midway International Airport stands as a key facility for domestic travel with a sole but expansive terminal encompassing concourses A, B, and C. Travellers have access to rental cars, taxis, shuttles, and public transport, including limited international flights.

For more comprehensive international travel, Chicago O'Hare International Airport has four terminals, including the international-dedicated Terminal 5. It's well-connected by rental cars, taxis, limousines, and shuttles, along with the CTA "L" train. Lastly, Chicago Rockford International Airport offers domestic services from its one terminal with rental cars and taxis, yet with fewer public transit options. Make your flight from Toronto to Chicago as comfortable as possible by familiarizing yourself with each airport’s facilities.

Best time to fly from Toronto to Chicago

The best time to fly from Toronto to Chicago is during the spring (March to May) and autumn (September to November) when you can enjoy moderate temperatures ranging from 6°C to 20°C. These seasons provide a comfortable climate for exploring the city, with a lower likelihood of extreme weather disrupting your travel plans. Whether you're looking to catch the fresh bloom of spring or the crisp air of fall, these months offer the ideal conditions for your visit to Chicago.

Reasons to visit Chicago

When planning your trip to Chicago, check out these activities and attractions the city has to offer. Tap into the energy of Lollapalooza, a celebrated music festival that draws fans and top artists alike for an unforgettable experience. Rise above the city streets at the Willis Tower Skydeck to capture expansive views from one of the tallest buildings in the world. Find a moment of tranquility as you stroll through Millennium Park and gaze upon the renowned public art and architecture. Not to be missed, The Art Institute of Chicago houses a vast collection that spans thousands of years, offering insights into humanity's creative legacy.

Add hotel bookings and car hire to your Toronto to Chicago flight

Planning your trip to Chicago is easy and convenient with Skyscanner. Find the ideal vehicle for your stay from trusted car hire brands like Budget, Europcar, and Thrifty. Accommodation choices abound; select from well-known hotels such as The Palmer House Hilton, Hyatt Regency Chicago, or InterContinental Chicago Magnificent Mile, an IHG Hotel. Skyscanner helps you organize both your journey and comfortable stay in the Windy City.

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