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Cheap Flights from Toronto to Chicago Midway

Compare Toronto to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Toronto to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Toronto to Chicago Midway Airport? If you want to travel next month, return fares start from $337. Find the lowest prices on one-way and return tickets right here.
Chicago.$337 per passenger.Departing Thu, 9 Apr, returning Sat, 11 Apr.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 9 Apr, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sat, 11 Apr, arriving in Toronto Island.Price includes taxes and charges.From $337, select.
Chicago.$387 per passenger.Departing Mon, 4 May, returning Thu, 7 May.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon, 4 May, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Thu, 7 May, arriving in Toronto Island.Price includes taxes and charges.From $387, select.
Chicago.$390 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 $390, select.
Chicago.$392 per passenger.Departing Mon, 30 Mar, returning Sat, 4 Apr.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon, 30 Mar, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sat, 4 Apr, arriving in Toronto Island.Price includes taxes and charges.From $392, select.
Chicago.$405 per passenger.Departing Sat, 30 May, returning Fri, 5 Jun.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 30 May, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Fri, 5 Jun, arriving in Toronto Island.Price includes taxes and charges.From $405, select.
Chicago.$406 per passenger.Departing Tue, 2 Jun, returning Tue, 9 Jun.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue, 2 Jun, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Tue, 9 Jun, arriving in Toronto Island.Price includes taxes and charges.From $406, select.
Chicago.$460 per passenger.Departing Thu, 30 Apr, returning Mon, 15 Jun.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 30 Apr, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Mon, 15 Jun, arriving in Toronto Island.Price includes taxes and charges.From $460, select.
Chicago.$462 per passenger.Departing Thu, 24 Sep, returning Sun, 27 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Thu, 24 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 27 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From $462, select.
Chicago.$488 per passenger.Departing Sat, 28 Mar, returning Mon, 30 Mar.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 28 Mar, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Mon, 30 Mar, arriving in Toronto Island.Price includes taxes and charges.From $488, select.
Chicago.$532 per passenger.Departing Fri, 24 Jul, returning Sun, 26 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Fri, 24 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 26 Jul, arriving in Toronto Pearson International.Price includes taxes and charges.From $532, select.
Chicago.$541 per passenger.Departing Mon, 15 Jun, returning Sun, 5 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 Sun, 5 Jul, arriving in Toronto Island.Price includes taxes and charges.From $541, select.
Chicago.$555 per passenger.Departing Mon, 19 Oct, returning Fri, 23 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Mon, 19 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Fri, 23 Oct, arriving in Toronto Pearson International.Price includes taxes and charges.From $555, select.
Chicago.$555 per passenger.Departing Tue, 18 Aug, returning Thu, 20 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Tue, 18 Aug, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Thu, 20 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From $555, select.
Chicago.$555 per passenger.Departing Sun, 23 Aug, returning Sun, 13 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Sun, 23 Aug, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 13 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From $555, select.
Chicago.$556 per passenger.Departing Thu, 30 Jul, returning Mon, 3 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Thu, 30 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 3 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From $556, select.
Chicago.$586 per passenger.Departing Sat, 1 Aug, returning Sun, 2 Aug.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 1 Aug, arriving in Chicago Midway.Inbound direct flight with Porter Airlines departs from Chicago Midway on Sun, 2 Aug, arriving in Toronto Island.Price includes taxes and charges.From $586, select.

Find the cheapest month to fly from Toronto to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Toronto to Chicago Midway flights are currently cheapest in April.
Mar
from $488
Apr
from $337
May
from $387
Jun
from $406
Jul
from $532
Aug
from $555
Sep
from $462
Oct
from $555
Nov
from $604
Dec
from $623
Jan
Find prices
Feb
Find prices

Direct flights from Toronto to Chicago Midway

Toronto to Chicago Midway: Alternative routes

Compare routes from Toronto to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
ClosestCheapest
from $337
Search flights

Chicago O'Hare International

25km from central Chicago
from $374
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight found$337
Cheapest month to flyApril
Average flight time1 hr, 50 mins
Most popular airlinePorter Airlines
Average flights per week37

Check out these Chicago hotels

Ready to plan your stay? Other travellers rate these Chicago hotels for cleanliness, service and location.
Grand House
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The Neighborhood Hotel Little Italy
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Kasa Magnificent Mile Chicago
1.93 km from city centre
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Grand House
2.17 km from city centre
$159
Per night
The Neighborhood Hotel Little Italy
2.91 km from city centre
$487
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Kasa Magnificent Mile Chicago
1.93 km from city centre
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Explore top-rated hotels

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

The best price we found for a return flight from Toronto to Chicago Midway is $337. 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 Midway.
Porter Airlines, Porter Airlines Inc and Air Transat fly direct from Toronto to Chicago Midway.
As of March 2026, there are 37 flights per week flying from Toronto to Chicago Midway.
The cheapest month to fly from Toronto to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Toronto to Chicago Midway Airport on Thursday, 9 April 2026.
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 Midway 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.
The cheapest airline that flies to Chicago Midway is Porter Airlines .

Travelling from Toronto to Chicago Midway International Airport (MDW): What you need to know

  • Toronto's main base, Billy Bishop Toronto City Airport (YTZ), is where many great holidays begin. Explore the departure options from here when planning your flight from Toronto to Chicago Midway International Airport (MDW).

  • The timezone in Chicago is UTC-6, which is one hour behind Toronto. Chicago Midway International Airport is located in Chicago.

  • Arrive at the airport on time so you don't miss your flight from Toronto to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.

  • During popular months like July, you'll want to get to the airport earlier than usual. Arrive two hours before a domestic departure and four hours ahead of international flights when you fly during high season in general.

Airports in Toronto

Toronto Pearson International Airport (YYZ)

  • Travelling from central Toronto to YYZ takes about 25 minutes on public transport. If you ride-share, drive or take a taxi, you'll cover the 27 kilometres in 30 minutes or so, depending on traffic.

  • Want a hassle-free start to your holiday? Stay near Toronto Pearson International Airport. Whether you're catching an early flight from Toronto to Chicago Midway International Airport or prefer not to rush, these hotels are just what you're after:

  • Of the departures from Toronto Pearson International Airport, 64% land on schedule at their destination.

Billy Bishop Toronto City Airport (YTZ)

  • Catching a flight out of Billy Bishop Toronto City Airport (YTZ)? Direct Toronto to Chicago Midway International Airport (MDW) plane tickets can be booked from this popular hub.

  • You can board a direct flight from Toronto to MDW with Porter Airlines. This is one of the leading airlines operating this route out of YTZ.

  • Porter Airlines (Canada) Ltd has the largest share of bookings on the YTZ to MDW route.

  • The most punctual carrier is Porter Airlines (Canada) Ltd. Its Billy Bishop Toronto City Airport to Chicago Midway International Airport flights arrive as planned 69.15% of the time.

  • YTZ is around 3 kilometres from central Toronto. It'll take 10 minutes or so to get to the airport in a car from the city centre. Public transport takes approximately 20 minutes.

  • Got an early start? Think about staying at one of these hotels near Billy Bishop Toronto City Airport the day before your Toronto to MDW flight:

  • When it comes to flights staying on schedule, Billy Bishop Toronto City Airport has an on-time arrival rate of 62%.

John C. Munro Hamilton International Airport (YHM)

  • From central Toronto, YHM is around 72 kilometres away. It'll take you roughly 1 hour 10 minutes to arrive by car and 1 hour 50 minutes or so if you use public transport.

  • Make catching an early Toronto to Chicago Midway International Airport flight the easiest part of your journey. Book a room at one of these hotels close to John C. Munro Hamilton International Airport and head to your check-in counter feeling relaxed and unhurried:

  • Airports have an on-time performance rating that measures how often flights get to their destinations without delays. At YHM, that figure is 71%.

About Chicago Midway International Airport (MDW)

  • Book a hotel close to MDW if you're catching a late flight from Toronto to Chicago Midway International Airport. Pick one of these options and avoid the hassle of a long transfer:

  • Pick up a Chicago Midway International Airport rental car and discover Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are top providers you can book with here.

  • Booking your vehicle around four weeks in advance of your Toronto to Chicago Midway International Airport flight can help you get a cheaper deal.

  • The street address for MDW is 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • From Chicago Midway International Airport, central Chicago is around 16 kilometres away. It takes about 25 minutes to get to the city centre by car.

  • If you're travelling on public transport, expect a journey of around 30 minutes.

How to find the cheapest flights from Toronto to Chicago Midway International Airport (MDW)

  • $198 is currently the lowest price for a one-way ticket from Toronto to Chicago Midway International Airport. A return flight starts from $337. These fares may change based on demand.

  • To find cheap flights from Toronto to MDW, book ahead. Airlines tend to offer lower fares when tickets are first released.

  • The 'Whole month' tool will show you the cheapest Toronto to Chicago Midway International Airport tickets across each month. It's a good way to find a bargain if your plans are flexible.

  • Stay on top of deals for plane tickets from Toronto to MDW by creating a Price Alert. We'll send you an email or push notification on the app when a lower fare pops up.

  • Filters make it easier to find a bargain for your flight from Toronto to Chicago Midway International Airport. Choose the airlines, flight times and number of stops that match your plans. Then sort the results by 'Cheapest' to find the best price quickly.

The best time to fly from Toronto to Chicago Midway International Airport (MDW)

  • Think about the kind of experience you want when deciding the best time to fly. July is the quietest month to visit Chicago. March is when most people book flights from Toronto to Chicago Midway International Airport (MDW), which may be ideal if you enjoy travelling when it's busier.

  • Before locking in your Toronto to MDW plane ticket, consider what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • January has temperatures of between -12ºC and 3ºC. Search for cheap tickets from Toronto to Chicago Midway International Airport around that time if you want to travel in cooler conditions.

More about Chicago

Explore more of the United States

  • Indianapolis is just one of the many places in the United States waiting to be explored once you've seen Chicago. Around 257 kilometres away to the southeast, its top attractions include Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

  • Milwaukee is another standout destination in the United States and is around 137 kilometres north of Chicago. No journey is complete without a visit to Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Plan the rest of your trip from Toronto to Chicago

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