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Billy Bishop Toronto City Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from NZD 231 and round-trip from NZD 337. Based on Trip.com's latest 7-day flight data.

      • Cheapest nonstop
        YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Tue, Oct 20 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Mon, Oct 26 | Porter Airlines
        NZD 337 NZD 474
        28% off
        28% off
        NZD 474 NZD 337
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sun, Oct 11 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Sun, Oct 18 | Porter Airlines
        NZD 337 NZD 474
        28% off
        28% off
        NZD 474 NZD 337
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sat, Oct 17 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Fri, Oct 23 | Porter Airlines
        NZD 338 NZD 474
        28% off
        28% off
        NZD 474 NZD 338
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Thu, Oct 22 | Porter Airlines
        MDW 11:45
        1h 40m
        Direct
        YTZ 14:25
        Chicago - Toronto | Sat, Oct 24 | Porter Airlines
        NZD 338
        28% off
        NZD 474 NZD 338
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Wed, Oct 28 | Porter Airlines
        ORD 18:20
        1h 46m
        Direct
        YTZ 21:06
        Chicago - Toronto | Tue, Nov 3 | Porter Airlines
        NZD 338
        28% off
        NZD 474 NZD 338
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Mon, Oct 26 | Porter Airlines
        ORD 12:20
        1h 46m
        Direct
        YTZ 15:06
        Chicago - Toronto | Fri, Oct 30 | Porter Airlines
        NZD 338
        28% off
        NZD 474 NZD 338
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Sat, Oct 24 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Wed, Oct 28 | Porter Airlines
        NZD 344
        27% off
        NZD 474 NZD 344
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Sat, Oct 10 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Wed, Oct 14 | Porter Airlines
        NZD 344
        27% off
        NZD 474 NZD 344
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Fri, Oct 16 | Porter Airlines
        MDW 11:45
        1h 40m
        Direct
        YTZ 14:25
        Chicago - Toronto | Thu, Oct 22 | Porter Airlines
        NZD 351
        26% off
        NZD 474 NZD 351
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Thu, Oct 15 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Thu, Oct 22 | Porter Airlines
        NZD 351
        26% off
        NZD 474 NZD 351
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Wed, Oct 21 | Porter Airlines
        MDW 11:45
        1h 40m
        Direct
        YTZ 14:25
        Chicago - Toronto | Sun, Oct 25 | Porter Airlines
        NZD 355
        25% off
        NZD 474 NZD 355
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Tue, Oct 27 | Porter Airlines
        ORD 07:05
        6h 16m
        1 stop
        YTZ 14:21
        Chicago - Toronto | Sun, Nov 1 | Air Canada
        NZD 346
        27% off
        NZD 474 NZD 346
      • YTO 13:00
        17h 25m
        1 stop
        CHI 14:00
        Toronto - Chicago | Sat, Oct 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        YTO 16:00
        Chicago - Toronto | Mon, Oct 12 | Normal Airline
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      • Cheapest nonstop
        YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Sun, Oct 25 | Porter Airlines
        NZD 231 NZD 551
        57% off
        57% off
        NZD 551 NZD 231
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sun, Oct 25 | Air Transat
        NZD 269 NZD 551
        51% off
        51% off
        NZD 551 NZD 269
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Wed, Oct 28 | Porter Airlines
        NZD 357 NZD 551
        35% off
        35% off
        NZD 551 NZD 357
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Fri, Oct 23 | Porter Airlines
        NZD 366
        34% off
        NZD 551 NZD 366
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Tue, Oct 20 | Porter Airlines
        NZD 366
        34% off
        NZD 551 NZD 366
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sat, Oct 24 | Porter Airlines
        NZD 366
        34% off
        NZD 551 NZD 366
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Mon, Oct 26 | Porter Airlines
        NZD 381
        31% off
        NZD 551 NZD 381
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Tue, Oct 27 | Porter Airlines
        NZD 388
        30% off
        NZD 551 NZD 388
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Wed, Oct 21 | Porter Airlines
        NZD 395
        28% off
        NZD 551 NZD 395
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sat, Oct 24 | Air Transat
        NZD 397
        28% off
        NZD 551 NZD 397
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Thu, Oct 22 | Porter Airlines
        NZD 408
        26% off
        NZD 551 NZD 408
      • YTZ 10:10
        1h 50m
        Direct
        MDW 11:00
        Toronto - Chicago | Wed, Oct 28 | Air Transat
        NZD 413
        25% off
        NZD 551 NZD 413
      • YTO 13:00
        17h 25m
        1 stop
        CHI 14:00
        Toronto - Chicago | Sat, Oct 10 | Normal Airline
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Displayed flight fares from Billy Bishop Toronto City Airport to Chicago Midway International Airport are based on average prices across airlines for the next 3 months according to the latest Trip.com data.

Trip.com Price Insights: Flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport

What is the cheapest month to fly from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

The data is based on the past 12 months and shows the average one-way ticket prices from Billy Bishop Toronto City Airport to Chicago Midway International Airport for each month in the Trip.com database.

Based on Trip.com's data from the past 12 months, the cheapest one-way flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport are usually in February, with an average price of NZD 287. It is best to avoid October, when the average price can reach NZD 461.

NZD 461
NZD 374
NZD 287
NZD 200
    Cheapest
  • NZD 461
    Oct
  • NZD 339
    Nov
  • NZD 356
    Dec
  • NZD 317
    Jan
  • NZD 287
    Feb
  • NZD 302
    Mar
  • NZD 287
    Apr
  • NZD 344
    May
  • NZD 319
    Jun
  • NZD 362
    Jul
  • NZD 336
    Aug
  • NZD 297
    Sep

What is the cheapest month to fly return from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

The data is based on the past 12 months and shows the average monthly return fares from Billy Bishop Toronto City Airport to Chicago Midway International Airport in the Trip.com database.

Based on Trip.com's data from the past 12 months, February is often the month to find the lowest fares from Billy Bishop Toronto City Airport to Chicago Midway International Airport, with an average price of NZD 392. October is usually the most expensive month, with an average price reaching NZD 637.

NZD 637
NZD 515
NZD 392
NZD 270
    Cheapest
  • NZD 637
    Oct
  • NZD 527
    Nov
  • NZD 525
    Dec
  • NZD 560
    Jan
  • NZD 392
    Feb
  • NZD 518
    Mar
  • NZD 488
    Apr
  • NZD 484
    May
  • NZD 478
    Jun
  • NZD 507
    Jul
  • NZD 499
    Aug
  • NZD 450
    Sep

What is the cheapest day of the week to fly from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

The data is based on the past 12 months and shows the average ticket prices from Billy Bishop Toronto City Airport to Chicago Midway International Airport for each day of the week in the Trip.com database.

Based on Trip.com's data from the past 12 months, the cheapest departure day from Billy Bishop Toronto City Airport to Chicago Midway International Airport is Monday, with average prices usually lower than other days. Avoid departing on Friday as prices are typically highest on that day.

NZD 343
NZD 332
NZD 320
NZD 309
  • NZD 320
    Mon
  • NZD 341
    Tue
  • NZD 328
    Wed
  • NZD 336
    Thu
  • NZD 343
    Fri
  • NZD 339
    Sat
  • NZD 337
    Sun

Which airline offers the cheapest flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

The cheapest airline flying from Billy Bishop Toronto City Airport to Chicago Midway International Airport is Porter Airlines (from NZD 231) among 2 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Porter Airlines
From NZD 231
Air Transat
From NZD 269

Find more flights and airlines

What is the flight schedule from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

Check the schedule for flights from Toronto to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. PD2387

    Billy Bishop Toronto City Airport

    09:30

    YTZ

    1h 50m

    10:20

    MDW

    S M T W T F S
    Search

  2. PD2393

    Billy Bishop Toronto City Airport

    15:50

    YTZ

    1h 50m

    16:40

    MDW

    S M T W T F S
    Search

  3. TS7314

    Billy Bishop Toronto City Airport

    13:45

    YTZ

    1h 50m

    14:35

    MDW

    S M T W T F S
    Search

  4. TS7060

    Billy Bishop Toronto City Airport

    10:10

    YTZ

    1h 50m

    11:00

    MDW

    S M T W T F S
    Search
Find more flights and airlines

About Billy Bishop Toronto City Airport and Chicago Midway International Airport

Learn about Billy Bishop Toronto City Airport (YTZ) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 712.43km
Cheapest one-way ticket price NZD 231
Cheapest return ticket price NZD 337

FAQs for Billy Bishop Toronto City Airport to Chicago Midway International Airport Flights

  • How long is the flight from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

    Billy Bishop Toronto City Airport to Chicago Midway International Airport takes about 1 hour 32 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 4 daily flights from Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW).
  • The earliest flight from Billy Bishop Toronto City Airport to Chicago Midway International Airport departs at 10:10, and the last departs at 13:45, with about 2 flights per day. Flight times may change, so please check the latest departure and arrival times before you travel.
  • The route from Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around NZD 568 in October, the most expensive month to book this route.
    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.
  • Porter Airlines is a very popular airline operating an average of 1249 flights per month.
  • One-way flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport currently start from NZD 231, and round-trip fares start from NZD 337. The current lowest fare is a Porter Airlines flight departing on Sun, Oct 25; prices may vary depending on availability.
  • Yes. Porter Airlines operate direct flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport, with an average flight time of 1 hour 29 minutes, and around 14 weekly flights. Actual flight frequency may vary by season.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from Billy Bishop Toronto City Airport to Chicago Midway International Airport is NZD 410. Prices may vary depending on the departure date, airline, and availability.
  • Porter Airlines and Air Transat are the most popular budget airlines flying from Billy Bishop Toronto City Airport to Chicago Midway International Airport, with one-way fares starting from NZD 231. Compare final prices carefully, as baggage, seat selection and payment fees may apply.
  • Billy Bishop Toronto City Airport to Chicago Midway International Airport operates around 14 weekly flights, mainly by Porter Airlines. Actual frequency may vary during holidays and seasonal schedule adjustments.
  • Enter Billy Bishop Toronto City Airport and Chicago Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

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Note: Prices shown on this page are the estimated lowest prices and include all taxes and fees found in the last 24 hours.

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Prices displayed on this page are all-inclusive (including taxes, fuel surcharges, civil aviation development fund, etc.), with all fees confirmed before payment. Fees for luggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours—sometimes even in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the cancellation and change policies for each flight ticket during the booking process, including any fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply according to the airline's ticket policy.
Cancellation/change due to a flight schedule change:
If the flight schedule has changed and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please visit the customer support pages.