Cheap Flights from Chicago (CHIA) to Toronto Island (YTZ)

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Find the cheapest month or even day of the year to fly to Toronto Island

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Flight deals from Chicago to Toronto Island

Looking for a cheap last-minute deal or the best return flight from Chicago to Toronto Island Airport? If you want to travel next month, return fares start from £139. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Toronto Island

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

Direct flights from Chicago to Toronto Island

Chicago to Toronto: Flight information

The things to know before you go.
Cheapest flight found£53
Cheapest month to flyMay
Average flight time1 hr, 42 mins
Most popular airlineAir Transat
Average flights per week224

Finding cheap flights from Chicago to Toronto Island: Frequently asked questions

The best price we found for a return flight from Chicago to Toronto Island is £128. 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 41 minutes is the average flight time from Chicago to Toronto Island.
Air Transat, Porter Airlines and Porter Airlines Inc fly direct from Chicago to Toronto Island.
As of April 2026, there are 112 flights per week flying from Chicago to Toronto Island.
The cheapest month to fly from Chicago to Toronto Island is usually July.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Toronto Island Airport on Wednesday, 8 July 2026.
Yes – the average flight time is 1 hour and 41 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 Toronto Island 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 Toronto is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Toronto Island is Porter Airlines .

Flying from Chicago to Billy Bishop Toronto City Airport (YTZ): What you need to know

  • Lay the groundwork for your adventure by considering where you'll take off for your flight from Chicago to Billy Bishop Toronto City Airport (YTZ). Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the two main airports in Chicago.

  • Around 1 hour 40 minutes is the typical travel time on a direct Chicago to Billy Bishop Toronto City Airport flight.

  • The timezone in Toronto is UTC-5, which is one hour ahead of Chicago. Billy Bishop Toronto City Airport is located in Toronto.

  • Chicago O'Hare International Airport (ORD) to Billy Bishop Toronto City Airport (YTZ) is the busiest route. You can choose from 8 direct services every week between ORD and YTZ.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport on time to board your flight from Chicago to YTZ.

  • If you're flying during a peak month like July, make your way to the airport even earlier. You'll want to arrive up to four hours before an international flight and two hours ahead of a domestic departure. Check-in and security lines are longer during peak periods like Christmas and New Year.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Go straight to your destination from Chicago O'Hare International Airport (ORD). Nonstop flights from Chicago to Billy Bishop Toronto City Airport (YTZ) are available from here.

  • When departing from ORD, you can catch a direct flight from Chicago to Billy Bishop Toronto City Airport with Air Canada.

  • Air Canada is the airline with the highest passenger demand for flights from ORD to YTZ.

  • Travelling from central Chicago to ORD takes around 45 minutes on public transport. If you ride-share, drive or grab a taxi, you'll cover the 27 kms (17 miles) in 30 minutes or so, depending on traffic.

  • Want a stress-free start to your break? Stay near Chicago O'Hare International Airport. Whether you're boarding an early flight from Chicago to Billy Bishop Toronto City Airport or want to avoid feeling rushed, these hotels are just what you're after:

  • When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 70% of flights meet their scheduled arrival time.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Planning to leave from Chicago Midway International Airport (MDW)? Direct Chicago to Billy Bishop Toronto City Airport (YTZ) plane tickets are available from here.

  • From MDW, direct flights from Chicago to YTZ are available with Porter Airlines.

  • Porter Airlines (Canada) Ltd ranks number one in bookings on the MDW to YTZ route.

  • Want to fly with a carrier that won't keep you waiting? Choose Porter Airlines (Canada) Ltd. 84.44% of its flights between Chicago Midway International Airport and Billy Bishop Toronto City Airport arrive on schedule.

  • Using public transport, you can travel from central Chicago to MDW in around 30 minutes. The airport is roughly 16 kms (10 miles) away, and getting there by car will take approximately 25 minutes.

  • Catching the earliest flight? You might like to check in to one of these accommodation options near Chicago Midway International Airport the day before your Chicago to YTZ flight:

  • Chicago Midway International Airport has an on-time performance of 76%. This figure reflects how often flights departing from this airport arrive on schedule.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 145 kms (90 miles) from central Chicago. Driving from the city centre to the airport takes about 1 hour 40 minutes. If you're considering public transport, expect a journey of around 2 hours.

  • Set yourself up for a smooth departure — stay near Chicago Rockford International Airport and know you'll be at the terminal with time to spare. Check in to one of these hotels the day before if you're catching an early Chicago to Billy Bishop Toronto City Airport flight:

  • The on-time performance rate of RFD is 71%. In simpler terms, that's how frequently flights from this airport arrive at their final stop as planned.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Billy Bishop Toronto City Airport (YTZ)

Getting from Billy Bishop Toronto City Airport (YTZ) to central Toronto

  • From Billy Bishop Toronto City Airport, central Toronto is around 3 kms (2 miles) away. It takes about 10 minutes to reach the city centre by car.

  • Travelling on public transport will take you around 20 minutes.

How to find the cheapest flights from Chicago to Billy Bishop Toronto City Airport (YTZ)

  • Currently, £53 is the best price we've found for a one-way ticket from Chicago to Billy Bishop Toronto City Airport. The cheapest price for a return flight is £128. Keep in mind fares can change due to demand at the time of booking.

  • Get your hands on cheap flights from Chicago to YTZ by booking one month ahead. According to our research, that's the sweet spot for finding a bargain.

  • June is when you're most likely to land a good deal on a Chicago to Billy Bishop Toronto City Airport ticket. If you're looking to travel during a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • You don't need to search every day to find out if fares have dropped when you set up a Price Alert. We'll let you know when a better deal comes up on plane tickets from Chicago to YTZ.

  • Bag the best deal on a flight from Chicago to Billy Bishop Toronto City Airport with the help of the filters. Choose your preferred arrival and departure times, number of stops and airlines. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest.'

The best time to fly from Chicago to Billy Bishop Toronto City Airport (YTZ)

  • It's time to decide your travel dates for your flight from Chicago to Billy Bishop Toronto City Airport (YTZ). November is the most popular month to visit Toronto. If a slower pace sounds more appealing, go in January.

  • The warmest month in Toronto is July, with temperatures ranging between 15ºC and 28ºC. Lock in your Chicago to YTZ plane ticket then if this is the type of weather you enjoy.

  • February sees temperatures of between -15ºC and 3ºC. Search for cheap tickets from Chicago to Billy Bishop Toronto City Airport around that time if you like cooler conditions.

More about Toronto

  • Start your Toronto trip off on the right foot by choosing the perfect place to stay. Once you've booked your flight from Chicago to Billy Bishop Toronto City Airport, check out our range of accommodation options including:

  • There are plenty of exciting things to do in Toronto when you're ready to see the sights. Kick off your itinerary at CN Tower followed by The Top CN Tower and Royal Ontario Museum.

Explore more of Canada

  • Toronto has plenty to offer, but there are so many other corners of Canada you'll want to see. Around 161 kms (100 miles) southwest of Toronto, a visit to London will keep you busy. Don't miss top attractions like Forks of the Thames River, Fanshawe Pioneer Village and Storybook Gardens.

  • Around 241 kms (150 miles) east of Toronto, Kingston is another essential stop in Canada. Get a taste of what this destination has to offer at Fort Henry, Rideau Canal - Jones Falls Defensible Lockmasters House and Kingston Penitentiary.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.