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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 HK$1,379 and round-trip from HK$1,489. Based on Trip.com's latest 7-day flight data.

    • Cheapest
      YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 24 | Porter Airlines
      HK$1,379 HK$3,088
      55% off
      55% off
      HK$3,088 HK$1,379
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 24 | Air Transat
      HK$1,600 HK$3,443
      54% off
      54% off
      HK$3,443 HK$1,600
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sun, Oct 25 | Porter Airlines
      HK$1,709 HK$3,407
      50% off
      50% off
      HK$3,407 HK$1,709
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Porter Airlines
      HK$1,914
      38% off
      HK$3,088 HK$1,914
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sun, Oct 25 | Air Transat
      HK$1,983
      42% off
      HK$3,407 HK$1,983
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Air Transat
      HK$2,233
      28% off
      HK$3,088 HK$2,233
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Mon, Oct 26 | Porter Airlines
      HK$2,261
      34% off
      HK$3,407 HK$2,261
    • YTZ 10:10
      1h 50m
      Direct
      MDW 11:00
      Toronto - Chicago | Fri, Oct 23 | Porter Airlines
      HK$2,261
      34% off
      HK$3,407 HK$2,261
    • YTZ 10:10
      1h 50m
      Direct
      MDW 11:00
      Toronto - Chicago | Thu, Oct 22 | Porter Airlines
      HK$2,261
      34% off
      HK$3,407 HK$2,261
    • YTO 13:00
      17h 25m
      1 stop
      CHI 14:00
      Toronto - Chicago | Fri, Oct 23 | Normal Airline
      Find more flights
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    • Cheapest nonstop
      YTZ 10:10
      1h 50m
      Direct
      MDW 11:00
      Toronto - Chicago | Tue, Oct 27 | Porter Airlines
      MDW 11:45
      1h 40m
      Direct
      YTZ 14:25
      Chicago - Toronto | Thu, Oct 29 | Porter Airlines
      HK$1,489 HK$3,939
      62% off
      62% off
      HK$3,939 HK$1,489
    • YTZ 10:10
      1h 50m
      Direct
      MDW 11:00
      Toronto - Chicago | Tue, Oct 27 | Air Transat
      MDW 11:45
      1h 40m
      Direct
      YTZ 14:25
      Chicago - Toronto | Thu, Oct 29 | Porter Airlines
      HK$1,822 HK$3,939
      54% off
      54% off
      HK$3,939 HK$1,822
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 30 | Porter Airlines
      ORD 18:20
      1h 46m
      Direct
      YTZ 21:06
      Chicago - Toronto | Thu, Nov 5 | Porter Airlines
      HK$2,708 HK$3,939
      31% off
      31% off
      HK$3,939 HK$2,708
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Thu, Oct 29 | Porter Airlines
      ORD 18:20
      1h 46m
      Direct
      YTZ 21:06
      Chicago - Toronto | Thu, Nov 5 | Porter Airlines
      HK$2,708
      31% off
      HK$3,939 HK$2,708
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Mon, Nov 2 | Porter Airlines
      ORD 12:20
      1h 46m
      Direct
      YTZ 15:06
      Chicago - Toronto | Fri, Nov 6 | Porter Airlines
      HK$2,773
      30% off
      HK$3,939 HK$2,773
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 31 | Porter Airlines
      MDW 11:45
      1h 40m
      Direct
      YTZ 14:25
      Chicago - Toronto | Mon, Nov 2 | Porter Airlines
      HK$2,815
      28% off
      HK$3,939 HK$2,815
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sun, Nov 1 | Porter Airlines
      ORD 18:20
      1h 46m
      Direct
      YTZ 21:06
      Chicago - Toronto | Fri, Nov 6 | Porter Airlines
      HK$2,825
      28% off
      HK$3,939 HK$2,825
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Thu, Oct 29 | Air Transat
      ORD 18:20
      1h 46m
      Direct
      YTZ 21:06
      Chicago - Toronto | Thu, Nov 5 | Air Transat
      HK$3,161
      20% off
      HK$3,939 HK$3,161
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 30 | Air Transat
      ORD 12:20
      1h 46m
      Direct
      YTZ 15:06
      Chicago - Toronto | Thu, Nov 5 | Air Transat
      HK$3,161
      20% off
      HK$3,939 HK$3,161
    • YTO 13:00
      17h 25m
      1 stop
      CHI 14:00
      Toronto - Chicago | Fri, Oct 23 | Normal Airline
      CHI 15:00
      6h
      Direct
      YTO 16:00
      Chicago - Toronto | Sun, Oct 25 | Normal Airline
      Find more flights
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    • Cheapest nonstop
      YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 24 | Porter Airlines
      HK$1,379 HK$3,088
      55% off
      55% off
      HK$3,088 HK$1,379
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Porter Airlines
      HK$1,914 HK$3,088
      38% off
      38% off
      HK$3,088 HK$1,914
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Air Transat
      HK$2,233 HK$3,088
      28% off
      28% off
      HK$3,088 HK$2,233
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Thu, Oct 22 | Porter Airlines
      HK$2,563
      17% off
      HK$3,088 HK$2,563
    • YTO 13:00
      17h 25m
      1 stop
      CHI 14:00
      Toronto - Chicago | Fri, Oct 23 | Normal Airline
      Find more flights
      Find more flights
    • Cheapest nonstop
      YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 24 | Porter Airlines
      HK$1,379 HK$3,088
      55% off
      55% off
      HK$3,088 HK$1,379
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Porter Airlines
      HK$1,914 HK$3,088
      38% off
      38% off
      HK$3,088 HK$1,914
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Air Transat
      HK$2,233 HK$3,088
      28% off
      28% off
      HK$3,088 HK$2,233
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Thu, Oct 22 | Porter Airlines
      HK$2,563
      17% off
      HK$3,088 HK$2,563
    • YTO 13:00
      17h 25m
      1 stop
      CHI 14:00
      Toronto - Chicago | Fri, Oct 23 | Normal Airline
      Find more flights
      Find more flights
    • Cheapest nonstop
      YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 24 | Porter Airlines
      HK$1,379 HK$3,088
      55% off
      55% off
      HK$3,088 HK$1,379
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Porter Airlines
      HK$1,914 HK$3,088
      38% off
      38% off
      HK$3,088 HK$1,914
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Air Transat
      HK$2,233 HK$3,088
      28% off
      28% off
      HK$3,088 HK$2,233
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Thu, Oct 22 | Porter Airlines
      HK$2,563
      17% off
      HK$3,088 HK$2,563
    • YTO 13:00
      17h 25m
      1 stop
      CHI 14:00
      Toronto - Chicago | Fri, Oct 23 | Normal Airline
      Find more flights
      Find more flights
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Air Transat
      HK$2,233 HK$3,443
      35% off
      35% off
      HK$3,443 HK$2,233
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Fri, Oct 23 | Porter Airlines
      HK$1,914 HK$3,443
      44% off
      44% off
      HK$3,443 HK$1,914
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Thu, Oct 22 | Air Transat
      HK$2,857 HK$3,443
      17% off
      17% off
      HK$3,443 HK$2,857
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 24 | Air Transat
      HK$1,600
      54% off
      HK$3,443 HK$1,600
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Sat, Oct 24 | Porter Airlines
      HK$1,379
      60% off
      HK$3,443 HK$1,379
    • YTZ 13:45
      1h 50m
      Direct
      MDW 14:35
      Toronto - Chicago | Thu, Oct 22 | Porter Airlines
      HK$2,563
      26% off
      HK$3,443 HK$2,563
    • YTO 13:00
      17h 25m
      1 stop
      CHI 14:00
      Toronto - Chicago | Fri, Oct 23 | Normal Airline
      Find more flights
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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 February, with an average price of HK$1,262. It is best to avoid October, when the average price can reach HK$1,963.

HK$1,963
HK$1,613
HK$1,262
HK$912
    Cheapest
  • HK$1,963
    Oct
  • HK$1,493
    Nov
  • HK$1,570
    Dec
  • HK$1,395
    Jan
  • HK$1,262
    Feb
  • HK$1,329
    Mar
  • HK$1,263
    Apr
  • HK$1,516
    May
  • HK$1,406
    Jun
  • HK$1,596
    Jul
  • HK$1,480
    Aug
  • HK$1,309
    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 HK$1,725. October is usually the most expensive month, with an average price reaching HK$2,503.

HK$2,503
HK$2,114
HK$1,725
HK$1,336
    Cheapest
  • HK$2,503
    Oct
  • HK$2,323
    Nov
  • HK$2,316
    Dec
  • HK$2,471
    Jan
  • HK$1,725
    Feb
  • HK$2,282
    Mar
  • HK$2,151
    Apr
  • HK$2,133
    May
  • HK$2,107
    Jun
  • HK$2,235
    Jul
  • HK$2,202
    Aug
  • HK$1,983
    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 Tuesday, with average prices usually lower than other days. Avoid departing on Friday as prices are typically highest on that day.

HK$1,530
HK$1,450
HK$1,370
HK$1,290
  • HK$1,430
    Mon
  • HK$1,370
    Tue
  • HK$1,445
    Wed
  • HK$1,469
    Thu
  • HK$1,530
    Fri
  • HK$1,510
    Sat
  • HK$1,494
    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 HK$1,627) among 2 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Porter Airlines
From HK$1,627
Air Transat
From HK$1,885

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

    - M T W T F -
    Search

  2. TS7060

    Billy Bishop Toronto City Airport

    10:10

    YTZ

    1h 50m

    11:00

    MDW

    - M T W T F -
    Search

  3. PD2393

    Billy Bishop Toronto City Airport

    15:50

    YTZ

    1h 50m

    16:40

    MDW

    - M T W T F -
    Search

  4. TS7314

    Billy Bishop Toronto City Airport

    13:45

    YTZ

    1h 50m

    14:35

    MDW

    - M T W T F -
    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 HK$1,379
Cheapest return ticket price HK$1,489

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 36 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 HK$2,857 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 HK$1,709, and round-trip fares start from HK$1,489. 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 34 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 HK$1,933. 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 HK$1,709. 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.

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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Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
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