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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 JPY 19,520 and round-trip from JPY 28,380. Based on Trip.com's latest 7-day flight data.

      • Cheapest nonstop
        YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Thu, Sep 24 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Wed, Sep 30 | Porter Airlines
        JPY 28,380 JPY 37,170
        24% off
        24% off
        JPY 37,170 JPY 28,380
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Fri, Oct 16 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Thu, Oct 22 | Porter Airlines
        JPY 29,720 JPY 37,170
        20% off
        20% off
        JPY 37,170 JPY 29,720
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Fri, Oct 23 | Porter Airlines
        ORD 12:20 PM
        1h 46m
        Nonstop
        YTZ 3:06 PM
        Chicago - Toronto | Tue, Oct 27 | Porter Airlines
        JPY 29,720 JPY 37,170
        20% off
        20% off
        JPY 37,170 JPY 29,720
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Tue, Oct 13 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Fri, Oct 16 | Porter Airlines
        JPY 29,740
        20% off
        JPY 37,170 JPY 29,740
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Wed, Oct 7 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Wed, Oct 14 | Porter Airlines
        JPY 29,790
        20% off
        JPY 37,170 JPY 29,790
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Wed, Oct 14 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Sun, Oct 18 | Porter Airlines
        JPY 29,840
        20% off
        JPY 37,170 JPY 29,840
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 10 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Sat, Oct 17 | Porter Airlines
        JPY 29,840
        20% off
        JPY 37,170 JPY 29,840
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Sun, Oct 18 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Tue, Oct 20 | Porter Airlines
        JPY 29,840
        20% off
        JPY 37,170 JPY 29,840
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 24 | Porter Airlines
        ORD 6:20 PM
        1h 46m
        Nonstop
        YTZ 9:06 PM
        Chicago - Toronto | Fri, Oct 30 | Porter Airlines
        JPY 29,840
        20% off
        JPY 37,170 JPY 29,840
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Thu, Oct 22 | Porter Airlines
        ORD 12:20 PM
        1h 46m
        Nonstop
        YTZ 3:06 PM
        Chicago - Toronto | Mon, Oct 26 | Porter Airlines
        JPY 29,840
        20% off
        JPY 37,170 JPY 29,840
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Thu, Oct 15 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Sun, Oct 18 | Porter Airlines
        JPY 29,860
        20% off
        JPY 37,170 JPY 29,860
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Thu, Oct 1 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Sat, Oct 3 | Porter Airlines
        JPY 30,100
        19% off
        JPY 37,170 JPY 30,100
      • YTO 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Toronto - Chicago | Fri, Sep 25 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        YTO 4:00 PM
        Chicago - Toronto | Sun, Sep 27 | Normal Airline
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      • Cheapest nonstop
        YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sun, Sep 27 | Porter Airlines
        JPY 19,520 JPY 25,680
        24% off
        24% off
        JPY 25,680 JPY 19,520
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sun, Oct 25 | Porter Airlines
        JPY 19,620 JPY 25,680
        24% off
        24% off
        JPY 25,680 JPY 19,620
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 24 | Porter Airlines
        JPY 20,250 JPY 25,680
        21% off
        21% off
        JPY 25,680 JPY 20,250
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Fri, Oct 23 | Porter Airlines
        JPY 20,300
        21% off
        JPY 25,680 JPY 20,300
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Mon, Oct 12 | Porter Airlines
        JPY 20,440
        20% off
        JPY 25,680 JPY 20,440
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Fri, Oct 16 | Porter Airlines
        JPY 20,440
        20% off
        JPY 25,680 JPY 20,440
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 3 | Porter Airlines
        JPY 20,510
        20% off
        JPY 25,680 JPY 20,510
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sun, Oct 18 | Porter Airlines
        JPY 20,730
        19% off
        JPY 25,680 JPY 20,730
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 17 | Porter Airlines
        JPY 20,730
        19% off
        JPY 25,680 JPY 20,730
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Thu, Oct 15 | Porter Airlines
        JPY 20,750
        19% off
        JPY 25,680 JPY 20,750
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Tue, Oct 20 | Porter Airlines
        JPY 20,770
        19% off
        JPY 25,680 JPY 20,770
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sun, Oct 4 | Air Transat
        JPY 20,800
        19% off
        JPY 25,680 JPY 20,800
      • YTO 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Toronto - Chicago | Fri, Sep 25 | 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 database.

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

What is the cheapest month for one-way flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

Data is based on average one-way flight prices from Billy Bishop Toronto City Airport to Chicago Midway International Airport in Trip.com's database over the past 12 months.

Based on Trip.com’s data from the past 12 months, if you’re looking for a low-cost one-way ticket from Billy Bishop Toronto City Airport to Chicago Midway International Airport, the best time to buy is in February, with an average price of JPY 25,290. You’ll want to avoid October, when the average price can reach as high as JPY 40,720.

JPY 40,720
JPY 33,005
JPY 25,290
JPY 17,575
    Cheapest
  • JPY 25,660
    Sep
  • JPY 40,720
    Oct
  • JPY 29,920
    Nov
  • JPY 31,460
    Dec
  • JPY 27,940
    Jan
  • JPY 25,290
    Feb
  • JPY 26,620
    Mar
  • JPY 25,310
    Apr
  • JPY 30,380
    May
  • JPY 28,170
    Jun
  • JPY 31,980
    Jul
  • JPY 29,660
    Aug

What’s the cheapest month to fly round-trip 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 round-trip 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 typically the cheapest month to find flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport, with an average price of JPY 34,570. In contrast, October is usually the most expensive month, with average fares reaching JPY 53,280.

JPY 53,280
JPY 43,925
JPY 34,570
JPY 25,215
    Cheapest
  • JPY 36,530
    Sep
  • JPY 53,280
    Oct
  • JPY 46,550
    Nov
  • JPY 46,400
    Dec
  • JPY 49,510
    Jan
  • JPY 34,570
    Feb
  • JPY 45,720
    Mar
  • JPY 43,110
    Apr
  • JPY 42,740
    May
  • JPY 42,220
    Jun
  • JPY 44,780
    Jul
  • JPY 44,110
    Aug

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 day to depart from Billy Bishop Toronto City Airport to Chicago Midway International Airport is Monday, with average fares typically lower than other days. You’ll want to avoid flying on Friday, as ticket prices are usually the highest that day.

JPY 30,250
JPY 29,545
JPY 28,840
JPY 28,135
  • JPY 28,840
    Mon
  • JPY 29,850
    Tue
  • JPY 29,190
    Wed
  • JPY 29,930
    Thu
  • JPY 30,250
    Fri
  • JPY 29,200
    Sat
  • JPY 29,520
    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 JPY 19,520) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Porter Airlines
From JPY 19,520
Air Transat
From JPY 20,800
Apg Airlines
From JPY 21,220

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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. PD2393

    Billy Bishop Toronto City Airport

    3:50 PM

    YTZ

    1h 50m

    4:40 PM

    MDW

    S M T W T F S
    Search

  2. PD2387

    Billy Bishop Toronto City Airport

    9:30 AM

    YTZ

    1h 50m

    10:20 AM

    MDW

    S M T W T F S
    Search

  3. TS7314

    Billy Bishop Toronto City Airport

    1:45 PM

    YTZ

    1h 50m

    2:35 PM

    MDW

    S M T W T F S
    Search

  4. TS7060

    Billy Bishop Toronto City Airport

    10:10 AM

    YTZ

    1h 50m

    11:00 AM

    MDW

    S M T W T F S
    Search
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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 712.43 km
Cheapest one-way ticket price JPY 19,520
Cheapest return ticket price JPY 28,380

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 35 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 JPY 48,200 in September, the most expensive month to book this route.
  • The earliest flight departs from Billy Bishop Toronto City Airport (YTZ) at 09:15 and arrives in Chicago Midway International Airport (MDW) at 10:05.
  • The latest flight departs from Billy Bishop Toronto City Airport (YTZ) at 18:15 and arrives in Chicago Midway International Airport (MDW) at 19:02.
    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Chicago Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.
  • 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 JPY 19,520, and round-trip fares start from JPY 28,380. The current lowest fare is a Porter Airlines flight departing on Sun, Sep 27; 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 32 minutes, and around 13 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 JPY 24,850. 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 JPY 19,520. 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 10 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 estimated lowest price and include all taxes and fees found in the last 24 hours.

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

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Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

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