Cheap Flights from Toronto to Chicago from RM757

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Flight deals from Toronto to Chicago

Looking for a cheap last-minute deal or the best return flight from Toronto to Chicago? If you want to travel next month, return fares start from RM757. Find the lowest prices on one-way and return tickets right here.

Chicago.RM757 per passenger.Departing Sat, 11 Apr, returning Sat, 18 Apr.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 11 Apr, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sat, 18 Apr, arriving in Toronto Island.Price includes taxes and charges.From RM757, select.

Chicago.RM765 per passenger.Departing Wed, 6 May, returning Wed, 13 May.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed, 6 May, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Wed, 13 May, arriving in Toronto Island.Price includes taxes and charges.From RM765, select.

Chicago.RM802 per passenger.Departing Fri, 24 Apr, returning Fri, 1 May.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Fri, 24 Apr, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 1 May, arriving in Toronto Island.Price includes taxes and charges.From RM802, select.

Chicago.RM839 per passenger.Departing Wed, 10 Jun, returning Sun, 14 Jun.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Island on Wed, 10 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Sun, 14 Jun, arriving in Toronto Island.Price includes taxes and charges.From RM839, select.

Chicago.RM852 per passenger.Departing Wed, 27 May, returning Mon, 1 Jun.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Wed, 27 May, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Mon, 1 Jun, arriving in Toronto Pearson International.Price includes taxes and charges.From RM852, select.

Chicago.RM862 per passenger.Departing Mon, 30 Mar, returning Fri, 3 Apr.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Mon, 30 Mar, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Fri, 3 Apr, arriving in Toronto Pearson International.Price includes taxes and charges.From RM862, select.

Chicago.RM891 per passenger.Departing Thu, 3 Sep, returning Wed, 9 Sep.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 3 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Porter Airlines departs from Chicago O'Hare International on Wed, 9 Sep, arriving in Toronto Island.Price includes taxes and charges.From RM891, select.

Chicago.RM988 per passenger.Departing Thu, 30 Apr, returning Sun, 14 Jun.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Thu, 30 Apr, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Sun, 14 Jun, arriving in Toronto Island.Price includes taxes and charges.From RM988, select.

Chicago.RM1,043 per passenger.Departing Tue, 31 Mar, returning Tue, 31 Mar.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Tue, 31 Mar, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Tue, 31 Mar, arriving in Toronto Pearson International.Price includes taxes and charges.From RM1,043, select.

Chicago.RM1,116 per passenger.Departing Sun, 24 May, returning Mon, 10 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Sun, 24 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 10 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From RM1,116, select.

Chicago.RM1,120 per passenger.Departing Tue, 7 Apr, returning Thu, 17 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Tue, 7 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Thu, 17 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From RM1,120, select.

Chicago.RM1,175 per passenger.Departing Fri, 11 Sep, returning Thu, 1 Oct.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Fri, 11 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Porter Airlines departs from Chicago O'Hare International on Thu, 1 Oct, arriving in Toronto Island.Price includes taxes and charges.From RM1,175, select.

Chicago.RM1,175 per passenger.Departing Sat, 22 Aug, returning Thu, 3 Sep.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 22 Aug, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago O'Hare International on Thu, 3 Sep, arriving in Toronto Island.Price includes taxes and charges.From RM1,175, select.

Chicago.RM1,200 per passenger.Departing Wed, 27 May, returning Mon, 10 Aug.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Wed, 27 May, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Mon, 10 Aug, arriving in Toronto Island.Price includes taxes and charges.From RM1,200, select.

Chicago.RM1,208 per passenger.Departing Mon, 15 Jun, returning Sat, 4 Jul.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon, 15 Jun, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sat, 4 Jul, arriving in Toronto Island.Price includes taxes and charges.From RM1,208, select.

Chicago.RM1,222 per passenger.Departing Wed, 5 Aug, returning Mon, 10 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Wed, 5 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 10 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From RM1,222, select.

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 April.

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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	RM757
Cheapest month to fly	April
Average flight time	1 hr, 57 mins
Most popular airline	United
Average flights per week	754

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The Robey, Chicago, a Member of Design Hotels

5.38 km from city centre

RM1,167

Per night

Chicago Parthenon Hostel

1.46 km from city centre

RM630

Per night

Grand House

2.17 km from city centre

RM362

Per night

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Finding cheap flights from Toronto to Chicago: Frequently asked questions

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 return flights from Toronto to Chicago?

The best price we found for a return flight from Toronto to Chicago is RM757. 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 57 minutes is the average flight time from Toronto to Chicago.

Which airlines fly direct from Toronto to Chicago?

United, Air Canada and Republic Airways fly direct from Toronto to Chicago.

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

As of March 2026, there are 750 flights per week flying from Toronto to Chicago.

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

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

Which is the cheapest airport to fly into in Chicago?

If you're flying from Toronto, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from RM757.

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 Saturday, 11 April 2026.

Can I get a direct flight from Toronto to Chicago?

Yes – the average flight time is 1 hour and 57 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 March, the average temperature is usually around 3°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 from Toronto to Chicago with?

The cheapest airline that flies to Chicago is Porter Airlines .

Travelling from Toronto to Chicago: what you need to know

When searching for your flight from Toronto to Chicago, there's a range of airports you can take off from. Pearson International Airport (YYZ), Billy Bishop Toronto City Airport (YTZ) and Region of Waterloo International Airport (YKF) are among Toronto's main terminals.
When choosing where to land in Chicago, O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the major entry points.
The average length of a direct Toronto to Chicago flight is 1 hour 55 minutes.
Chicago's timezone is UTC-5, making Chicago one hour behind Toronto.
The most popular route for flights from Toronto to Chicago is from Pearson International Airport (YYZ) to O'Hare International Airport (ORD). Choose from 116 services every week between these two airports. If you'd like to get going as soon as possible, the earliest flight from YYZ to ORD is the 06:15 American Airlines option. If you prefer to leave later in the day, the final scheduled service is at 21:00 with United Airlines.
To ensure you make your Toronto to Chicago flight, leave plenty of time for things like baggage drop and finding your gate. Turning up two hours before international departures and one hour before domestic flights is the standard rule.
Be prepared for bigger queues in popular months like August. Arriving up to four hours in advance for international flights and two hours for a domestic departure is a smart move.

How to find the cheapest flights from Toronto to Chicago

To secure cheap Toronto to Chicago flights, reserve your journey two months ahead of your departure.
Plan your trip for May. That's the best month for scoring the biggest deals on plane tickets from Toronto to Chicago. If you're flexible with your dates, use the 'Whole month' tool to see the cheapest price across each month.
Cut down on the time spent looking for cheap flights from Toronto to Chicago by creating a Price Alert. You'll receive an email or notification through the app when a new discounted fare appears.
Tailor your travel plans using filters. Pick your ideal arrival and departure times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' Toronto to Chicago flights.

Flying from Toronto

Pearson International Airport (YYZ)

If you're searching for a direct flight from Toronto to Chicago, you can depart from Pearson International Airport (YYZ). Get from YYZ to O'Hare International Airport (ORD) in one continuous trip.
You'll have your choice of airlines that offer direct Toronto to Chicago plane tickets out of YYZ. Book your seat with one of these:
Travelling from central Toronto to YYZ takes around 50 minutes by public transport. If you drive, ride-share or grab a cab, you'll cover the 19 kilometres in 25 minutes or so, depending on traffic conditions.
After a hassle-free start to your holiday? Stay near Pearson International Airport. Whether you have an early flight from Toronto to Chicago or want to avoid feeling rushed, these hotels are perfect:
Of all flights leaving Pearson International Airport, 63.97% land on time at their destination.

Billy Bishop Toronto City Airport (YTZ)

Consider booking your direct flight from Toronto to Chicago out of Billy Bishop Toronto City Airport (YTZ). Nonstop connections from YTZ will get you to Chicago Midway International Airport (MDW).
Porter Airlines offers direct Toronto to Chicago plane tickets from YTZ. Book your favourite aisle (or window) seat and arrive at your destination in a single stretch.
You can reach YTZ from the centre of Toronto in about 35 minutes by car, depending on traffic. The journey on public transport will take roughly 40 minutes to cover the 3 kilometres or so.
Want to treat yourself to an extra night away before your flight from Toronto to Chicago? Unwind in a hotel near Billy Bishop Toronto City Airport before your trip officially starts. These stays are calling your name:
Billy Bishop Toronto City Airport has an on-time performance of 62%. This figure shows how frequently flights that take off from this airport land on time.

Region of Waterloo International Airport (YKF)

YKF is roughly 80 kilometres from central Toronto. Driving from the city centre to the terminal takes about 1 hour 15 minutes. If you're planning to take public transport, expect a journey of around 4 hours 5 minutes.
Sleep a little longer, move a little slower, and still make your Toronto to Chicago flight with plenty of time to spare. These accommodation options near Region of Waterloo International Airport make departure day a breeze if you're jetting off early:
Flights that leave from YKF arrive at their destination within the scheduled time frame 63.64% of the time.

Arriving in Chicago

O'Hare International Airport (ORD)

The distance from O'Hare International Airport (ORD) to central Chicago is roughly 26 kilometres. It'll take you around 35 minutes to reach the centre driving.
When travelling on public transport, expect a journey time of roughly 55 minutes.
The last thing you need is a lengthy journey to your hotel if you're landing late on a flight from Toronto to Chicago. Check in to one of these accommodation options near ORD instead:
Fast-track your adventure by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's usual tourist stops.
Lock in the best rate by booking your ride from O'Hare International Airport about four weeks before your trip.
You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) is about 14 kilometres from central Chicago. Once you've hopped off your flight from Toronto to Chicago, it'll take you approximately 20 minutes to reach the heart of the city in a ride-share or cab.
If you're travelling on public transport, it'll take approximately 45 minutes.
After your flight from Toronto to Chicago, tuck yourself in at a hotel close to MDW. These are some comfortable options that'll help you slip into relaxation mode:
The fastest way to get to where you're going is with a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and be on your way in a flash.
Don't pay more than you need to. Reserving your ride four weeks before your arrival at MDW can land you a better rate.
Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Hop off your flight from Toronto to Chicago and travel to your hotel or jump right into sightseeing. Central Chicago is around 129 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach driving.
If you use public transport, the journey takes around 4 hours 15 minutes.
Start your trip without stressing over how to reach your next stop with a Chicago Rockford International Airport rental car. Find your perfect set of wheels with reliable companies here like Budget, Alamo and National.
If you're looking for a certain model or make, booking early increases your chances of snagging what you want. Reserve your ride from RFD at least a few weeks ahead of your flight from Toronto to Chicago.
Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

It's time to choose your dates for your flight from Toronto to Chicago. August is the most popular month to visit Chicago. If you like a more relaxed atmosphere, go in January.
The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Toronto to Chicago ticket then if you enjoy this type of weather.
Look for cheap flights from Toronto to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Start your Chicago trip right by choosing the ideal place to stay. As soon as you've booked your flight from Toronto to Chicago, browse our range of hotels including:
There are so many things to discover in this city it can be hard to work out where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are top attractions which should be on any well-planned Chicago itinerary.

Explore more of United States

Chicago is easy to fall in love with, but there are so many other parts of United States waiting to be discovered. About 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the go. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without experiencing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.