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Billy Bishop Toronto City Airport to Chicago Midway International Airport flight

Search for flights from Toronto to Chicago and check out affordable one-way and round-trip options.

      • Cheapest nonstop
        YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sat, Jun 13 | Porter Airlines
        MDW 10:25
        1h 40m
        Direct
        YTZ 13:05
        Chicago - Toronto | Sat, Jun 20 | Porter Airlines
        JPY 27,550 JPY 36,130
        24% off
        24% off
        JPY 36,130 JPY 27,550
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Thu, May 14 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Sat, May 16 | Porter Airlines
        JPY 28,150 JPY 36,130
        22% off
        22% off
        JPY 36,130 JPY 28,150
      • YTZ 08:45
        1h 50m
        Direct
        MDW 09:35
        Toronto - Chicago | Thu, Jun 4 | Porter Airlines
        MDW 10:15
        1h 40m
        Direct
        YTZ 12:55
        Chicago - Toronto | Sat, Jun 6 | Porter Airlines
        JPY 28,360 JPY 36,130
        22% off
        22% off
        JPY 36,130 JPY 28,360
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Fri, May 29 | Porter Airlines
        MDW 10:30
        1h 40m
        Direct
        YTZ 13:10
        Chicago - Toronto | Tue, Jun 2 | Porter Airlines
        JPY 28,410
        21% off
        JPY 36,130 JPY 28,410
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Thu, May 28 | Porter Airlines
        MDW 10:30
        1h 40m
        Direct
        YTZ 13:10
        Chicago - Toronto | Sat, May 30 | Porter Airlines
        JPY 28,760
        20% off
        JPY 36,130 JPY 28,760
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Wed, Jun 17 | Porter Airlines
        MDW 10:25
        1h 40m
        Direct
        YTZ 13:05
        Chicago - Toronto | Sat, Jun 20 | Porter Airlines
        JPY 28,760
        20% off
        JPY 36,130 JPY 28,760
      • YTZ 08:45
        1h 50m
        Direct
        MDW 09:35
        Toronto - Chicago | Tue, Jun 16 | Porter Airlines
        MDW 10:15
        1h 40m
        Direct
        YTZ 12:55
        Chicago - Toronto | Thu, Jun 18 | Porter Airlines
        JPY 28,780
        20% off
        JPY 36,130 JPY 28,780
      • YTZ 08:45
        1h 50m
        Direct
        MDW 09:35
        Toronto - Chicago | Thu, Jun 11 | Porter Airlines
        MDW 10:15
        1h 40m
        Direct
        YTZ 12:55
        Chicago - Toronto | Sat, Jun 13 | Porter Airlines
        JPY 28,870
        20% off
        JPY 36,130 JPY 28,870
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Sat, May 16 | Porter Airlines
        MDW 10:30
        1h 40m
        Direct
        YTZ 13:10
        Chicago - Toronto | Thu, May 21 | Porter Airlines
        JPY 29,170
        19% off
        JPY 36,130 JPY 29,170
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Sat, May 30 | Porter Airlines
        MDW 10:25
        1h 40m
        Direct
        YTZ 13:05
        Chicago - Toronto | Thu, Jun 4 | Porter Airlines
        JPY 29,980
        17% off
        JPY 36,130 JPY 29,980
      • YTO 13:00
        17h 25m
        1 stop
        CHI 14:00
        Toronto - Chicago | Fri, May 15 | Normal Airline
        CHI 15:00
        6h
        Direct
        YTO 16:00
        Chicago - Toronto | Sun, May 17 | Normal Airline
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      • Cheapest nonstop
        YTZ 15:35
        1h 49m
        Direct
        MDW 16:24
        Toronto - Chicago | Fri, Jun 26 | Apg Airlines
        JPY 16,490 JPY 23,750
        31% off
        31% off
        JPY 23,750 JPY 16,490
      • YTZ 08:45
        1h 50m
        Direct
        MDW 09:35
        Toronto - Chicago | Thu, Jun 11 | Porter Airlines
        JPY 17,260 JPY 23,750
        27% off
        27% off
        JPY 23,750 JPY 17,260
      • YTZ 08:45
        1h 50m
        Direct
        MDW 09:35
        Toronto - Chicago | Wed, Jun 3 | Porter Airlines
        JPY 17,670 JPY 23,750
        26% off
        26% off
        JPY 23,750 JPY 17,670
      • YTZ 08:50
        1h 50m
        Direct
        MDW 09:40
        Toronto - Chicago | Mon, Jun 22 | Porter Airlines
        JPY 17,700
        25% off
        JPY 23,750 JPY 17,700
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sat, Jun 27 | Porter Airlines
        JPY 17,930
        25% off
        JPY 23,750 JPY 17,930
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Mon, Jun 1 | Porter Airlines
        JPY 18,180
        23% off
        JPY 23,750 JPY 18,180
      • YTZ 08:45
        1h 50m
        Direct
        MDW 09:35
        Toronto - Chicago | Thu, Jun 4 | Porter Airlines
        JPY 18,230
        23% off
        JPY 23,750 JPY 18,230
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Wed, Jun 24 | Porter Airlines
        JPY 18,250
        23% off
        JPY 23,750 JPY 18,250
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sun, Jun 21 | Porter Airlines
        JPY 18,250
        23% off
        JPY 23,750 JPY 18,250
      • YTZ 08:50
        1h 50m
        Direct
        MDW 09:40
        Toronto - Chicago | Fri, Jun 12 | Air Transat
        JPY 19,710
        17% off
        JPY 23,750 JPY 19,710
      • YTO 13:00
        17h 25m
        1 stop
        CHI 14:00
        Toronto - Chicago | Fri, May 15 | Normal Airline
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Displayed flight fares from Toronto to Chicago 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 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 July, with an average price of JPY 22,960. It is best to avoid October, when the average price can reach JPY 40,090.

JPY 40,090
JPY 31,525
JPY 22,960
JPY 14,395
    Cheapest
  • JPY 31,170
    May
  • JPY 23,100
    Jun
  • JPY 22,960
    Jul
  • JPY 29,180
    Aug
  • JPY 23,050
    Sep
  • JPY 40,090
    Oct
  • JPY 29,460
    Nov
  • JPY 30,980
    Dec
  • JPY 27,520
    Jan
  • JPY 24,910
    Feb
  • JPY 26,220
    Mar
  • JPY 24,920
    Apr

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, September 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 JPY 32,810. October is usually the most expensive month, with an average price reaching JPY 52,460.

JPY 52,460
JPY 42,635
JPY 32,810
JPY 22,985
    Cheapest
  • JPY 39,970
    May
  • JPY 34,450
    Jun
  • JPY 37,970
    Jul
  • JPY 38,790
    Aug
  • JPY 32,810
    Sep
  • JPY 52,460
    Oct
  • JPY 45,840
    Nov
  • JPY 45,700
    Dec
  • JPY 48,750
    Jan
  • JPY 34,040
    Feb
  • JPY 45,020
    Mar
  • JPY 42,450
    Apr

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 Saturday, with average prices usually lower than other days. Avoid departing on Friday as prices are typically highest on that day.

JPY 29,350
JPY 27,655
JPY 25,960
JPY 24,265
    Cheapest
  • JPY 26,480
    Mon
  • JPY 28,190
    Tue
  • JPY 28,930
    Wed
  • JPY 26,770
    Thu
  • JPY 29,350
    Fri
  • JPY 25,960
    Sat
  • JPY 27,740
    Sun

Selected Airlines from Billy Bishop Toronto City Airport to Chicago Midway International Airport

See which airlines fly from Toronto to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

Porter Airlines
From JPY 17,700
Air Transat
From JPY 19,710
Apg Airlines
From JPY 19,950

Find more flights and airlines

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 - S
    Search

  4. TS7060

    Billy Bishop Toronto City Airport

    08:50

    YTZ

    1h 50m

    09:40

    MDW

    S M T W T F S
    Search
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Billy Bishop Toronto City Airport to Chicago Midway International Airport Flights Info

Flight distance712.43km
Cheapest one-way ticket priceJPY 16,490
Cheapest return ticket priceJPY 27,550

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

  • How long does it take to fly from Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW)?

    It takes around 1 hour 50 minutes to fly from Billy Bishop Toronto City Airport (ytz) to Chicago Midway International Airport(mdw).
  • There are around 3 daily flights from Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW).
  • Tickets cost around JPY 27,600 in June, making it the cheapest month to book. Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW) is a popular route, so don't forget to book your tickets in advance.
  • 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 41,650 in May, the most expensive month to book this route.
    • The distance from Chicago 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 Chicago O'Hare International Airport. The distance is around 25km.
  • Porter Airlines is a very popular airline operating an average of 1249 flights per month.

Find Cheap Flights with Trip.com

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 on 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, 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 were updated within the last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

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Cancellation/change due to a flight schedule change:
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