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Toronto Pearson International Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Toronto Pearson International Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from €126 and round-trip from €197. Based on Trip.com's latest 7-day flight data.

      • YYZ 12:10
        6h 50m
        1 stop
        MDW 18:00
        Toronto - Chicago | Tue, Oct 20 | Delta Air Lines
        ORD 11:19
        5h
        1 stop
        YYZ 17:19
        Chicago - Toronto | Thu, Oct 22 | Delta Air Lines
        €197 €320
        38% off
        38% off
        €320 €197
      • YYZ 09:45
        4h 6m
        1 stop
        MDW 12:51
        Toronto - Chicago | Mon, Nov 23 | Delta Air Lines
        ORD 14:44
        7h 13m
        1 stop
        YYZ 22:57
        Chicago - Toronto | Wed, Nov 25 | Delta Air Lines
        €199 €320
        38% off
        38% off
        €320 €199
      • YYZ 14:20
        4h 44m
        1 stop
        MDW 18:04
        Toronto - Chicago | Fri, Nov 13 | Delta Air Lines
        MDW 09:30
        6h 50m
        1 stop
        YYZ 17:20
        Chicago - Toronto | Tue, Nov 17 | Delta Air Lines
        €242 €320
        24% off
        24% off
        €320 €242
      • YYZ 09:45
        4h 6m
        1 stop
        MDW 12:51
        Toronto - Chicago | Sat, Nov 21 | Delta Air Lines
        ORD 08:29
        4h 1m
        1 stop
        YYZ 13:30
        Chicago - Toronto | Wed, Nov 25 | Delta Air Lines
        €246
        23% off
        €320 €246
      • YYZ 09:45
        4h 16m
        1 stop
        MDW 13:01
        Toronto - Chicago | Sat, Dec 12 | Delta Air Lines
        ORD 17:05
        5h 2m
        1 stop
        YYZ 23:07
        Chicago - Toronto | Tue, Dec 15 | Delta Air Lines
        €246
        23% off
        €320 €246
      • YYZ 06:00
        7h 47m
        1 stop
        MDW 12:47
        Toronto - Chicago | Thu, Oct 29 | Delta Air Lines
        MDW 09:29
        6h 50m
        1 stop
        YYZ 17:19
        Chicago - Toronto | Tue, Nov 3 | Delta Air Lines
        €246
        23% off
        €320 €246
      • YYZ 06:00
        7h 51m
        1 stop
        MDW 12:51
        Toronto - Chicago | Sun, Nov 22 | Delta Air Lines
        MDW 09:30
        6h 50m
        1 stop
        YYZ 17:20
        Chicago - Toronto | Wed, Nov 25 | Delta Air Lines
        €247
        23% off
        €320 €247
      • YYZ 06:00
        4h 32m
        1 stop
        MDW 09:32
        Toronto - Chicago | Fri, Oct 30 | Delta Air Lines
        MDW 13:27
        8h 29m
        1 stop
        YYZ 22:56
        Chicago - Toronto | Sun, Nov 1 | Delta Air Lines
        €248
        23% off
        €320 €248
      • YYZ 12:15
        6h 49m
        1 stop
        MDW 18:04
        Toronto - Chicago | Wed, Nov 18 | Delta Air Lines
        MDW 09:30
        6h 50m
        1 stop
        YYZ 17:20
        Chicago - Toronto | Tue, Nov 24 | Delta Air Lines
        €248
        23% off
        €320 €248
      • YYZ 09:45
        4h 6m
        1 stop
        MDW 12:51
        Toronto - Chicago | Thu, Nov 26 | Delta Air Lines
        MDW 09:30
        6h 50m
        1 stop
        YYZ 17:20
        Chicago - Toronto | Mon, Nov 30 | Delta Air Lines
        €248
        23% off
        €320 €248
      • YYZ 06:00
        4h 32m
        1 stop
        MDW 09:32
        Toronto - Chicago | Mon, Nov 2 | Delta Air Lines
        ORD 17:29
        4h 27m
        1 stop
        YYZ 22:56
        Chicago - Toronto | Fri, Nov 6 | Delta Air Lines
        €248
        23% off
        €320 €248
      • YYZ 12:10
        6h 50m
        1 stop
        MDW 18:00
        Toronto - Chicago | Wed, Nov 4 | Delta Air Lines
        ORD 08:29
        7h 50m
        1 stop
        YYZ 17:19
        Chicago - Toronto | Sun, Nov 8 | Delta Air Lines
        €249
        22% off
        €320 €249
      • YTO 13:00
        17h 25m
        1 stop
        CHI 14:00
        Toronto - Chicago | Thu, Oct 15 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        YTO 16:00
        Chicago - Toronto | Sat, Oct 17 | Normal Airline
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      • YYZ 12:15
        6h 49m
        1 stop
        MDW 18:04
        Toronto - Chicago | Mon, Nov 30 | Delta Air Lines
        €126 €193
        35% off
        35% off
        €193 €126
      • YYZ 14:25
        4h 36m
        1 stop
        MDW 18:01
        Toronto - Chicago | Sun, Dec 6 | Delta Air Lines
        €126 €193
        35% off
        35% off
        €193 €126
      • YYZ 06:00
        4h 37m
        1 stop
        MDW 09:37
        Toronto - Chicago | Sat, Dec 5 | Delta Air Lines
        €126 €193
        35% off
        35% off
        €193 €126
      • YYZ 06:00
        7h 51m
        1 stop
        MDW 12:51
        Toronto - Chicago | Fri, Nov 20 | Delta Air Lines
        €128
        34% off
        €193 €128
      • YYZ 12:10
        6h 50m
        1 stop
        MDW 18:00
        Toronto - Chicago | Mon, Oct 19 | Delta Air Lines
        €128
        34% off
        €193 €128
      • YYZ 06:00
        4h 32m
        1 stop
        MDW 09:32
        Toronto - Chicago | Mon, Nov 2 | Delta Air Lines
        €128
        34% off
        €193 €128
      • YYZ 06:00
        7h 51m
        1 stop
        MDW 12:51
        Toronto - Chicago | Mon, Nov 23 | Delta Air Lines
        €130
        33% off
        €193 €130
      • YYZ 06:00
        7h 51m
        1 stop
        MDW 12:51
        Toronto - Chicago | Wed, Nov 25 | Delta Air Lines
        €130
        33% off
        €193 €130
      • YYZ 06:00
        7h 48m
        1 stop
        MDW 12:48
        Toronto - Chicago | Thu, Nov 5 | Delta Air Lines
        €138
        28% off
        €193 €138
      • YYZ 06:00
        6h 25m
        1 stop
        MDW 11:25
        Toronto - Chicago | Sat, Nov 28 | Delta Air Lines
        €149
        23% off
        €193 €149
      • YYZ 09:45
        4h 16m
        1 stop
        MDW 13:01
        Toronto - Chicago | Mon, Dec 7 | Delta Air Lines
        €150
        22% off
        €193 €150
      • YYZ 06:00
        7h 51m
        1 stop
        MDW 12:51
        Toronto - Chicago | Fri, Nov 13 | Delta Air Lines
        €150
        22% off
        €193 €150
      • YTO 13:00
        17h 25m
        1 stop
        CHI 14:00
        Toronto - Chicago | Thu, Oct 15 | Normal Airline
        Find more flights
        Find more flights

Displayed flight fares from Toronto Pearson International 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.

Which airline offers the cheapest flights from Toronto Pearson International Airport to Chicago Midway International Airport?

The cheapest airline flying from Toronto Pearson International Airport to Chicago Midway International Airport is Delta Air Lines (from €126) among 2 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Delta Air Lines
From €126
WestJet
From €241

Find more flights and airlines

What is the flight schedule from Toronto Pearson International 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. DL5073

    Toronto Pearson International Airport

    09:45

    YYZ

    1h 33m

    Nonstop

    11:18

    DTW

    S M T W T F S
    Search

  2. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28

    DTW

    1h 19m

    Nonstop

    12:47

    MDW

    S M T W T F S

  3. DL5031

    Toronto Pearson International Airport

    06:00

    YYZ

    1h 40m

    Nonstop

    07:40

    DTW

    S M T W T F S
    Search

  4. DL4684

    Detroit Metropolitan Wayne County Airport

    09:10

    DTW

    1h 36m

    Nonstop

    09:46

    MDW

    S M T W T F S

  5. DL4978

    Toronto Pearson International Airport

    14:15

    YYZ

    1h 20m

    Nonstop

    15:35

    DTW

    S M T W T - S
    Search

  6. DL4677

    Detroit Metropolitan Wayne County Airport

    18:15

    DTW

    1h 22m

    Nonstop

    18:37

    MDW

    S M T W T F S

  7. DL5256

    Toronto Pearson International Airport

    12:15

    YYZ

    1h 20m

    Nonstop

    13:35

    DTW

    S M T W T F S
    Search

  8. DL4677

    Detroit Metropolitan Wayne County Airport

    18:15

    DTW

    1h 22m

    Nonstop

    18:37

    MDW

    S M T W T F S

  9. DL5031

    Toronto Pearson International Airport

    06:00

    YYZ

    1h 40m

    Nonstop

    07:40

    DTW

    S M T W T F S
    Search

  10. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28

    DTW

    1h 19m

    Nonstop

    12:47

    MDW

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

About Toronto Pearson International Airport and Chicago Midway International Airport

Learn about Toronto Pearson International Airport (YYZ) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 696.97 km
Cheapest one-way ticket price €126
Cheapest return ticket price €197

FAQs for Toronto Pearson International Airport to Chicago Midway International Airport Flights

  • What is the flight schedule from Toronto Pearson International Airport to Chicago Midway International Airport?

    The earliest flight from Toronto Pearson International Airport to Chicago Midway International Airport departs at 14:00, and the last departs at 14:00, with about 1 flights per day. Flight times may change, so please check the latest departure and arrival times before you travel.
    • The distance from O'Hare International Airport to downtown is about 25 km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.
  • One-way flights from Toronto Pearson International Airport to Chicago Midway International Airport currently start from €126, and round-trip fares start from €197. The current lowest fare is a Delta Air Lines flight departing on Mon, Nov 30; prices may vary depending on availability.
  • Yes. Delta Air Lines operate direct flights from Toronto Pearson International Airport to Chicago Midway International Airport, with an average flight time of 1 hour 14 minutes, and around 1 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 Toronto Pearson International Airport to Chicago Midway International Airport is €306. Prices may vary depending on the departure date, airline, and availability.
  • Toronto Pearson International Airport to Chicago Midway International Airport operates around 1 weekly flights, mainly by Delta Air Lines. Actual frequency may vary during holidays and seasonal schedule adjustments.
  • Enter Toronto Pearson International 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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