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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 €110 and round-trip from €168. Based on Trip.com's latest 7-day flight data.

      • Cheapest nonstop
        YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Sat, Oct 24 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Mon, Oct 26 | Porter Airlines
        €168 €245
        31% off
        31% off
        €245 €168
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Wed, Oct 21 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Tue, Oct 27 | Porter Airlines
        €168 €245
        31% off
        31% off
        €245 €168
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Mon, Oct 12 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Mon, Oct 19 | Porter Airlines
        €168 €245
        31% off
        31% off
        €245 €168
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sun, Oct 18 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Sat, Oct 24 | Porter Airlines
        €168
        31% off
        €245 €168
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Fri, Oct 23 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Sun, Oct 25 | Porter Airlines
        €168
        31% off
        €245 €168
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Thu, Oct 29 | Porter Airlines
        ORD 6:20 PM
        1h 46m
        Nonstop
        YTZ 9:06 PM
        Chicago - Toronto | Wed, Nov 4 | Porter Airlines
        €168
        31% off
        €245 €168
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Tue, Oct 27 | Porter Airlines
        ORD 12:20 PM
        1h 46m
        Nonstop
        YTZ 3:06 PM
        Chicago - Toronto | Sat, Oct 31 | Porter Airlines
        €168
        31% off
        €245 €168
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Tue, Oct 6 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Thu, Oct 8 | Porter Airlines
        €170
        31% off
        €245 €170
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Thu, Oct 8 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Sun, Oct 11 | Porter Airlines
        €170
        31% off
        €245 €170
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Fri, Oct 9 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Tue, Oct 13 | Porter Airlines
        €170
        31% off
        €245 €170
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Mon, Oct 5 | Porter Airlines
        MDW 11:45 AM
        1h 40m
        Nonstop
        YTZ 2:25 PM
        Chicago - Toronto | Fri, Oct 9 | Porter Airlines
        €170
        31% off
        €245 €170
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Sun, Oct 4 | Porter Airlines
        MDW 3:20 PM
        1h 40m
        Nonstop
        YTZ 6:00 PM
        Chicago - Toronto | Tue, Oct 6 | Porter Airlines
        €171
        30% off
        €245 €171
      • YTO 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Toronto - Chicago | Mon, Oct 5 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        YTO 4:00 PM
        Chicago - Toronto | Wed, Oct 7 | Normal Airline
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      • Cheapest nonstop
        YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Fri, Oct 23 | Porter Airlines
        €110 €236
        53% off
        53% off
        €236 €110
      • YTZ 10:10 AM
        1h 50m
        Nonstop
        MDW 11:00 AM
        Toronto - Chicago | Sun, Oct 11 | Porter Airlines
        €116 €236
        51% off
        51% off
        €236 €116
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 17 | Porter Airlines
        €117 €236
        50% off
        50% off
        €236 €117
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Fri, Oct 16 | Porter Airlines
        €117
        50% off
        €236 €117
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Wed, Oct 14 | Porter Airlines
        €117
        50% off
        €236 €117
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Fri, Oct 23 | Air Transat
        €131
        44% off
        €236 €131
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sun, Oct 11 | Air Transat
        €134
        43% off
        €236 €134
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Fri, Oct 16 | Air Transat
        €136
        42% off
        €236 €136
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Wed, Oct 14 | Air Transat
        €136
        42% off
        €236 €136
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 17 | Air Transat
        €136
        42% off
        €236 €136
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 24 | Apg Airlines
        €163
        31% off
        €236 €163
      • YTZ 1:45 PM
        1h 50m
        Nonstop
        MDW 2:35 PM
        Toronto - Chicago | Sat, Oct 24 | Air Transat
        €165
        30% off
        €236 €165
      • YTO 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Toronto - Chicago | Mon, Oct 5 | Normal Airline
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Flight fares from Billy Bishop Toronto City Airport to Chicago Midway International Airport are based on average airline prices for the next 3 months, according to Trip.com’s latest data.

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

Which month has the lowest one-way flight price from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

The data is based on the average one-way flight prices on Trip.com for flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport across different months over the past 12 months.

Based on Trip.com data from the past 12 months, if you’re looking for low one-way flight fares from Billy Bishop Toronto City Airport to Chicago Midway International Airport, the best time to book is in February, with an average price of €143. Try to avoid October, when prices are highest, averaging around €230.

€230
€187
€143
€100
    Cheapest
  • €163
    Sep
  • €230
    Oct
  • €169
    Nov
  • €178
    Dec
  • €158
    Jan
  • €143
    Feb
  • €150
    Mar
  • €143
    Apr
  • €171
    May
  • €159
    Jun
  • €180
    Jul
  • €167
    Aug

Which month is the cheapest for round-trip flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport?

The data is based on the average round-trip flight prices on Trip.com for flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport across different months over the past 12 months.

Based on Trip.com data from the past 12 months, February is usually the cheapest month to find flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport, with an average price of €195. In contrast, October is typically the most expensive month, with average prices reaching €300.

€300
€248
€195
€143
    Cheapest
  • €221
    Sep
  • €300
    Oct
  • €262
    Nov
  • €262
    Dec
  • €279
    Jan
  • €195
    Feb
  • €258
    Mar
  • €243
    Apr
  • €241
    May
  • €238
    Jun
  • €253
    Jul
  • €249
    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 average flight prices on Trip.com from Billy Bishop Toronto City Airport to Chicago Midway International Airport across different days of the week over the past 12 months.

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

€171
€167
€162
€158
  • €162
    Mon
  • €168
    Tue
  • €165
    Wed
  • €170
    Thu
  • €171
    Fri
  • €170
    Sat
  • €166
    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 €107) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Porter Airlines
From €107
Air Transat
From €125
Apg Airlines
From €129

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. 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
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 712.43 km
Cheapest one-way ticket price €110
Cheapest return ticket price €168

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 29 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 €266 in October, the most expensive month to book this route.
    • 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 €110, and round-trip fares start from €168. The current lowest fare is a Porter Airlines flight departing on Fri, Oct 23; 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 30 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 €192. 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 €110. 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 lowest estimated prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before payment. Charges for checked baggage, onboard meals, Wi-Fi, and other optional services may also appear in the flight cards where applicable.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and for many routes the data may refresh in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to 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 based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.