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Cheap flights from Toronto to Chicago Midway Airport from $119

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago Midway Airport departing on 5/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap Toronto to Chicago Midway Airport (YTO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago Midway Airport

Best Price Found

$119

Fastest flight time

1h 47m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto in the past 72 hours is $119. The best round-trip flight deal from Toronto to Chicago Midway Airport found on momondo in the last 72 hours is $204.
The fastest flight from Toronto to Chicago Midway Airport takes 1h 47m
Direct flights go from Toronto to Chicago Midway Airport every day.

How to get the cheapest flight ticket from Toronto to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

March. The cheapest time of year to fly to Chicago Midway Airport from Toronto is March. Most expensive is January

What is the cheapest day to depart Toronto for Chicago Midway Airport?

Monday. The cheapest day of the week is typically Monday. The most expensive is typically Wednesday

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

At noon. Toronto to Chicago Midway Airport flights are approximately 23% more expensive in the morning than at noon

What is the cheapest airline that flies to Chicago Midway Airport from Toronto?

Porter Airlines. Porter Airlines is the most popular carrier operating from Toronto to Chicago Midway Airport

How far in advance should you book Toronto to Chicago Midway Airport flights?

49 days before. The cheapest time to buy a flight from Toronto to Chicago Midway Airport is approximately 49 days to departure

How many flights depart from Toronto to Chicago Midway Airport on average per day?

As of March 2024, there are 2 flights per week flying from Toronto to Chicago Midway Airport. The most common time of day flights depart is 2:00PM, with 61% of flights taking off in the afternoon.

How many flights depart from Toronto to Chicago Midway Airport on average per week?

As of March 2024, there are 14 flights per week flying from Toronto to Chicago Midway Airport. The most common day of the week flights depart is Thursday, with 21% of flights taking off on this day.

When traveling from Toronto to Chicago, the most popular airport to fly into is Chicago Midway Airport. The majority of travelers flying into Chicago Midway Airport from Toronto are departing from Toronto Pearson Intl Airport. If you are looking for an alternate airport near Toronto Pearson Intl Airport, Toronto Island Airport is a great option and is located in Toronto. The least expensive flight option from Toronto to Chicago will typically be YTZ — MDW during the month of March with an average price of $204 RT.

Toronto Island Airport (YTZ) to Chicago Midway Airport (MDW)$204
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Toronto Pearson Intl Airport (YYZ) to Chicago Midway Airport (MDW)$254
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Easily compare round-trip flights from Toronto to Chicago Midway Airport

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Toronto to Chicago Midway Airport by changing tabs
Porter Airlines
Apr 25
YTZ8:50 pmToronto Island
1h 47m
MDW9:37 pmChicago Midway
May 2
MDW5:15 pmChicago Midway
1h 42m
YTZ7:57 pmToronto Island
Delta
Apr 18
YYZ12:30 pmToronto Pearson Intl
4h 54m
1 stop
MDW4:24 pmChicago Midway
Apr 24
MDW6:00 pmChicago Midway
3h 46m
1 stop
YYZ10:46 pmToronto Pearson Intl
Multiple Airlines
Apr 24
YTZ10:10 amToronto Island
8h 03m
1 stop
MDW5:13 pmChicago Midway
Apr 28
MDW8:40 amChicago Midway
1h 42m
YTZ11:22 amToronto Island
WestJet
Apr 17
YYZ6:04 pmToronto Pearson Intl
5h 10m
1 stop
MDW10:14 pmChicago Midway
Apr 20
MDW6:00 amChicago Midway
5h 10m
1 stop
YYZ12:10 pmToronto Pearson Intl
Porter Airlines
Apr 17
YTZ9:20 amToronto Island
1h 47m
MDW10:07 amChicago Midway
Apr 17
MDW5:15 pmChicago Midway
1h 42m
YTZ7:57 pmToronto Island
Porter Airlines
Apr 23
YTZ3:30 pmToronto Island
1h 47m
MDW4:17 pmChicago Midway
Apr 30
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island

Find the cheapest one-way flights from Toronto to Chicago Midway Airport

If you're looking for one-way flights from Toronto to Chicago Midway Airport, view some of our deals below provided by Delta and Porter Airlines
Porter Airlines
May 1
YTZ9:20 amToronto Island
1h 47m
MDW10:07 amChicago Midway
Delta
Apr 24
YYZ12:30 pmToronto Pearson Intl
4h 54m
1 stop
MDW4:24 pmChicago Midway
Multiple Airlines
May 1
YTZ10:10 amToronto Island
8h 03m
1 stop
MDW5:13 pmChicago Midway

Search last-minute flights to Chicago Midway Airport from Toronto

Find and compare round-trip flight prices for your last-minute flight from Toronto to Chicago Midway Airport
Porter Airlines
Apr 6
YTZ10:45 amToronto Island
1h 47m
MDW11:32 amChicago Midway
Apr 17
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island
Delta
Apr 10
YYZ6:15 amToronto Pearson Intl
3h 35m
1 stop
MDW8:50 amChicago Midway
Apr 17
MDW5:05 pmChicago Midway
5h 10m
1 stop
YYZ11:15 pmToronto Pearson Intl
WestJet
Apr 11
YYZ6:04 pmToronto Pearson Intl
5h 10m
1 stop
MDW10:14 pmChicago Midway
Apr 15
MDW11:20 amChicago Midway
6h 01m
1 stop
YYZ6:21 pmToronto Pearson Intl
Multiple Airlines
Apr 9
YYZ4:30 pmToronto Pearson Intl
9h 08m
1 stop
MDW12:38 amChicago Midway
Apr 14
MDW2:44 pmChicago Midway
25h 16m
1 stop
YYZ5:00 pmToronto Pearson Intl
Porter Airlines
Apr 7
YTZ8:50 pmToronto Island
1h 47m
MDW9:37 pmChicago Midway
Apr 13
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island
Delta
Apr 10
YYZ6:15 amToronto Pearson Intl
3h 35m
1 stop
MDW8:50 amChicago Midway
Apr 15
MDW11:20 amChicago Midway
6h 01m
1 stop
YYZ6:21 pmToronto Pearson Intl

Best airlines flying from Toronto to Chicago Midway Airport

Compare and see reviews for airlines that fly from Toronto to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $205Free CancellationRating
7.4
450 reviews
Search Porter Airlines flights
  • Porter Airlines Flights From Toronto to Chicago Midway Airport

    Porter Airlines is one of the most popular airlines flying from Toronto to Chicago Midway Airport, operating 14 flights/week on average for this route. A good Porter Airlines flight deal for Toronto to Chicago Midway Airport starts from $205 round-trip, up to an average price of $288. Our users have rated Porter Airlines at 7.4/10.


Porter Airlines flights from Toronto to Chicago Midway Airport

Our best Porter Airlines deals on Toronto to Chicago Midway Airport flight tickets
Porter Airlines
Apr 25
YTZ8:50 pmToronto Island
1h 47m
MDW9:37 pmChicago Midway
May 2
MDW5:15 pmChicago Midway
1h 42m
YTZ7:57 pmToronto Island
Porter Airlines
Apr 17
YTZ9:20 amToronto Island
1h 47m
MDW10:07 amChicago Midway
Apr 17
MDW5:15 pmChicago Midway
1h 42m
YTZ7:57 pmToronto Island
Porter Airlines
Apr 23
YTZ3:30 pmToronto Island
1h 47m
MDW4:17 pmChicago Midway
Apr 30
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island

Delta flights from Toronto to Chicago Midway Airport

Our best Delta deals on Toronto to Chicago Midway Airport flight tickets
Delta
Apr 18
YYZ12:30 pmToronto Pearson Intl
4h 54m
1 stop
MDW4:24 pmChicago Midway
Apr 24
MDW6:00 pmChicago Midway
3h 46m
1 stop
YYZ10:46 pmToronto Pearson Intl
Delta
Apr 23
YYZ6:15 amToronto Pearson Intl
3h 35m
1 stop
MDW8:50 amChicago Midway
Apr 29
MDW5:05 pmChicago Midway
5h 10m
1 stop
YYZ11:15 pmToronto Pearson Intl
Delta
Apr 24
YYZ12:30 pmToronto Pearson Intl
4h 54m
1 stop
MDW4:24 pmChicago Midway
Apr 29
MDW5:05 pmChicago Midway
5h 10m
1 stop
YYZ11:15 pmToronto Pearson Intl

  • How far is Toronto to Chicago Midway by plane?

    There are 443.1 mi between Toronto and Chicago Midway. Typically, this will take 1h 47m by plane in normal conditions.

  • When did momondo last update prices for flights from Toronto to Chicago Midway Airport?

    Prices for flights from Toronto to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Toronto to Chicago Midway Airport?

  • How old do you have to be to fly from Toronto to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.


Alternative routes for Toronto to Chicago Midway Airport

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Toronto to Chicago O'Hare Intl Airport Flights
Fastest flight time1h 52m
Cheapest price$232
Ottawa to Chicago O'Hare Intl Airport Flights
Fastest flight time2h 17m
Cheapest price$335
Ottawa to Chicago Midway Airport Flights
Fastest flight time3h 37m
Cheapest price$235
London, Ontario to Chicago O'Hare Intl Airport Flights
Fastest flight time4h 03m
Cheapest price$598
London, Ontario to Chicago Midway Airport Flights
Fastest flight time24h 11m
Cheapest price$1,811

Similar Toronto to Chicago Midway Airport flights

Flexible with your destination? Broaden your search and find flights similar to your Toronto to Chicago Midway Airport route

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Toronto to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Toronto which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Toronto to Chicago?

Once all potential Toronto to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


An easier way to manage your Chicago Midway Airport trip

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