YTO - MDW

$194 Find Cheap Flights from Toronto to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$332
Typical prices: $209-$360
Delta
Sat 12/1Sun 12/2
YYZ - MDW • 1 stop
Cheapest one-way
$195
Typical prices: $134-$252
Multiple Airlines
Thu 1/11
YYZ - MDW • 2 stops
Top routes
YTZ - MDW
Cheapest • 10% average savings
YYZ - MDW
Most popular
Insights
Insights
Avoid delays
Delta
Most punctual • 25% on-time
Afternoon
Best time • Fewest delays
Insights
Insights
When to book
25 weeks
in advance
Our data shows that travelers who book at least 25 weeks in advance save around 66% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 14% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Detroit Metropolitan Wayne County (DTW)
Cheapest • Avg $368 (round-trip)
Orlando (MCO)
Shortest trip • 24h 55m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Toronto to Midway (YTO-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto to Midway

Wed, Nov 25 - Sun, Nov 29
Delta Logo
6:00 am - 9:46 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 1:30 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 00m1 stop Detroit Metropolitan Wayne County
$326Delta
Thu, Nov 26 - Tue, Dec 1
Delta Logo
6:00 am - 11:25 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
$329Delta
Tue, Dec 1 - Tue, Dec 8
Delta Logo
6:00 am - 9:37 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
$329Delta
Sat, Nov 28 - Tue, Dec 1
Delta Logo
12:15 pm - 6:04 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 49m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
$329Delta
Thu, Nov 26 - Sun, Nov 29
Delta Logo
6:00 am - 11:25 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:31 pm - 10:57 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
$329Delta
Fri, Nov 27 - Tue, Dec 1
Delta Logo
6:00 am - 11:25 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:07 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
$329Delta
Tue, Dec 8 - Wed, Dec 9
Delta Logo
6:00 am - 9:37 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:37 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 43m1 stop Detroit Metropolitan Wayne County
$329Delta
Fri, Nov 27 - Sun, Nov 29
Delta Logo
6:00 am - 11:25 amYYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 25m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 5:20 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 50m1 stop Detroit Metropolitan Wayne County
$329Delta
Tue, Nov 17 - Wed, Nov 25
Delta Logo
2:20 pm - 6:04 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 44m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:31 pm - 10:57 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
$329Delta
Wed, Feb 10 - Mon, Feb 15
Delta Logo
6:10 am - 1:01 pmYYZ  Toronto Pearson Intl-MDW Chicago Midway
7h 51m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 pm - 10:59 pmMDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 18m1 stop Detroit Metropolitan Wayne County
$332Delta
Booking Insights

Price, demand and travel trends for Toronto to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Toronto to Chicago Midway Airport?

Round-trip flights from Toronto to Chicago Midway Airport typically range from $209 to $360. The lowest price found in the past 5 days was $332, on Delta.

What is the cheapest Toronto to Chicago Midway Airport flight route?

Toronto Island Airport (YTZ) to Chicago Midway Airport (MDW) is the cheapest Toronto to Chicago Midway Airport route, averaging $266 round-trip. Other Toronto to Chicago Midway Airport routes average $324, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Toronto to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Toronto to Chicago Midway Airport. It’s 9% cheaper than the average day, while Friday is the most expensive, with prices 8% higher.

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

•January is the cheapest month to fly from Toronto to Chicago Midway Airport at $230 round-trip.
•October ($310) and November ($301) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 34% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Toronto to Chicago Midway Airport the cheapest?

Flights from Toronto to Chicago Midway Airport are cheapest 25 weeks before departure. Booking in this window typically costs about 66% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Toronto to Chicago Midway Airport flights

Low season

February

Cheapest flight

$195
Beat the crowds with an average 41% drop in travelers.
The most popular month to fly with an average 66% increase in travelers.
One-way flight from Toronto Pearson Intl Airport to Chicago Midway Airport

When to book flights from Toronto to Midway

Are your dates flexible? Find out the best times to travel from Toronto to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Toronto to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Toronto to Chicago Midway Airport?

    Only Economy Class is available on flights from Toronto to Chicago Midway Airport.

  • How long is a flight from Toronto to Chicago Midway Airport?

    There are currently no nonstop flights available from Toronto to Chicago Midway Airport. Flights with 1 layover take between 4h 04m and 24h 55m in total, depending on the connection.

  • Do I need a passport to fly from Toronto to Chicago Midway Airport?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Toronto to Chicago Midway Airport flight?

    Round-trip flights from Toronto to Chicago Midway Airport range from $209 to $360, with an average of $267 over the past 12 months. Anything below $209 counts as a good deal.

  • How expensive are last-minute Toronto to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 59% above the $267 route average. Book 25 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Toronto to Chicago Midway Airport?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $266 round-trip, compared to $368 via a layover through Detroit Metropolitan Wayne County (DTW).

  • How does on-time performance compare across airlines flying from Toronto to Chicago Midway Airport?

    Delta is the only airline operating Toronto to Chicago Midway Airport flights. 25% of its flights are on time.

  • What is the standard checked-bag allowance on flights from Toronto to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $29–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Have flight prices from Toronto to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $332 to $1,526. That means the highest observed fare was about 5x higher than the lowest one.

  • How are flight prices from Toronto to Chicago Midway Airport looking right now?

    One-way fares from Toronto to Chicago Midway Airport are currently higher than usual. Average one-way flight prices are about $197, which is 6% above the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $86 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Toronto to Chicago Midway Airport?

    Flights from Toronto to Chicago Midway Airport may depart from several airports in Toronto area, including Toronto Region of Waterloo Intl (YKF), Toronto Island (YTZ) and Toronto Pearson Intl (YYZ). Flights usually arrive at Chicago Midway (MDW).

  • What time of day has the fewest delays on flights from Toronto to Chicago Midway Airport?

    Afternoon flights have the fewest delays on this route.

  • At what point is a flight considered delayed from Toronto to Chicago Midway Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Toronto to Chicago Midway Airport route, 75% of flights were delayed in the past 3 months, with delays averaging 1h 57m.

  • Which airports do connecting flights from Toronto to Chicago Midway Airport pass through?

    Connecting flights from Toronto to Chicago Midway Airport most commonly pass through:

    • Detroit Metropolitan Wayne County (DTW) - 98% of one-stop connections
    • Orlando (MCO) - 2% of one-stop connections

  • Can I save money by using flexible dates for flights from Toronto to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 17% on flights from Toronto to Chicago Midway Airport. Tuesday is the cheapest departure day at $243 round-trip on average, while Friday is the most expensive at $291, a difference of $48.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Toronto to Chicago Midway Airport?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 04m, compared with 24h 55m via Orlando (MCO).

  • What is the time difference between Toronto and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Toronto (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Toronto to Chicago Midway Airport flights?

    Among airlines operating Toronto to Chicago Midway Airport flights:

    • Porter Airlines: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Toronto to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Porter Airlines: a cabin bag and a checked bag in Economy Class
    • Air Transat: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Toronto to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Friday. On this route, Tuesday flights average $243, about $48 less than Friday fares (16% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 25 weeks before you fly. On this route, that window historically saves about 66% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Toronto to Chicago Midway Airport trip for January. Fares historically average $230 round-trip in that month - typically $80 less than the most expensive month, which is October (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

More options for your flight from Toronto to Midway

Complete your trip to Chicago with a hotel stay or car rental

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