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Toronto Pearson International Airport to Midway International Airport flight
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Cheap Flight Deals from Toronto Pearson International Airport to Midway International Airport

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

  • One way
  • Round-trip
sortSort: Price (Lowest)
  • Sort: Price (Lowest)
  • Sort: Departure (Earliest)
      • YYZ12:30
        5h 46m
        1 stop
        MDW17:16
        Toronto - Chicago|Sat, Oct 5|Delta Air Lines
        €123€169
        27% OFF
        27% OFF
        €169€123
      • YYZ12:20
        5h 43m
        1 stop
        MDW17:03
        Toronto - Chicago|Wed, Oct 23|Delta Air Lines
        €124€169
        26% OFF
        26% OFF
        €169€124
      • YYZ06:30
        8h 1m
        1 stop
        MDW13:31
        Toronto - Chicago|Mon, Oct 14|Delta Air Lines
        €130€169
        23% OFF
        23% OFF
        €169€130
      • YYZ06:00
        7h 32m
        1 stop
        MDW12:32
        Toronto - Chicago|Thu, Oct 31|Delta Air Lines
        €131
        €131
      • YYZ12:20
        5h 43m
        1 stop
        MDW17:03
        Toronto - Chicago|Tue, Nov 5|Delta Air Lines
        €131
        €131
      • YYZ12:15
        5h 47m
        1 stop
        MDW17:02
        Toronto - Chicago|Thu, Nov 21|Delta Air Lines
        €132
        €132
      • YYZ06:00
        7h 50m
        1 stop
        MDW12:50
        Toronto - Chicago|Tue, Dec 17|Delta Air Lines
        €133
        €133
      • YYZ12:20
        5h 44m
        1 stop
        MDW17:04
        Toronto - Chicago|Wed, Sep 25|Delta Air Lines
        €133
        €133
      • YYZ12:20
        5h 43m
        1 stop
        MDW17:03
        Toronto - Chicago|Wed, Oct 16|Delta Air Lines
        €133
        €133
      • YYZ06:30
        8h 1m
        1 stop
        MDW13:31
        Toronto - Chicago|Wed, Oct 9|Delta Air Lines
        €134
        €134
      • YYZ13:00
        3h 5m
        Direct
        MDW14:00
        Toronto - Chicago|Sun, Sep 29|Delta Air Lines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Selected Airlines from Toronto Pearson International Airport to 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.

Delta Air Lines
From €123
WestJet
From €150
Air Transat
From €161
Air Canada
From €649

Find more flights and airlines

Find Cheaper Flights from Toronto to Chicago. Enjoy direct flights with 2 airlines

Explore other flights from Toronto to Chicago to find the best alternative options.

  • Cheapest
    Porter Airlines
    YTZ
    15:30
    1h 47m
    Direct
    MDW
    16:17
    Billy Bishop Toronto City Airport - Midway International Airport
    Wed, Oct 9Porter Airlines
    €106
  • American Airlines
    YYZ
    06:30
    1h 54m
    Direct
    ORD
    07:24
    Toronto Pearson International Airport - O'Hare International Airport
    Wed, Oct 23American Airlines
    €117
  • Air Canada
    YTZ
    10:20
    5h 19m
    1 transfer
    ORD
    14:39
    Billy Bishop Toronto City Airport - O'Hare International Airport
    Wed, Oct 23Air Canada
    €119
  • Air Canada
    YTZ
    10:20
    5h 19m
    1 transfer
    ORD
    14:39
    Billy Bishop Toronto City Airport - O'Hare International Airport
    Wed, Oct 23Air Canada
    €119
    Find More Flights
Flight Schedule from Toronto Pearson International Airport to 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. DL5031

    Delta Air Lines

    06:00

    YYZ

    1.6h

    07:35

    DTW

    SMTWTFS
    Search

  2. DL3867

    Delta Air Lines

    12:15

    DTW

    1.2h

    12:28

    MDW

    SMTWT-S

  3. DL5031

    Delta Air Lines

    06:00

    YYZ

    1.6h

    07:35

    DTW

    SMTWTFS
    Search

  4. DL3858

    Delta Air Lines

    08:25

    DTW

    1.3h

    08:45

    MDW

    SMTWTFS

  5. DL3823

    Delta Air Lines

    06:30

    YYZ

    2.4h

    07:52

    MSP

    SMTWTFS
    Search

  6. DL3792

    Delta Air Lines

    11:58

    MSP

    1.6h

    13:37

    MDW

    SMTWT-S

  7. DL3823

    Delta Air Lines

    06:30

    YYZ

    2.4h

    07:52

    MSP

    SMTWTFS
    Search

  8. DL3799

    Delta Air Lines

    17:10

    MSP

    1.7h

    18:50

    MDW

    SMTWTFS

  9. DL3836

    Delta Air Lines

    09:45

    YYZ

    1.3h

    11:02

    DTW

    S--WT-S
    Search

  10. DL3869

    Delta Air Lines

    16:10

    DTW

    1.3h

    16:27

    MDW

    SMTWTFS

  11. DL5256

    Delta Air Lines

    13:50

    YYZ

    1.4h

    15:16

    DTW

    SMTWTFS
    Search

  12. DL3869

    Delta Air Lines

    16:10

    DTW

    1.3h

    16:27

    MDW

    SMTWTFS
Find more flights and airlines

Toronto Pearson International Airport to Midway International Airport Flights Info

Flight distance696.97km
Cheapest one-way ticket price€123
Cheapest return ticket price€232

FAQs for Toronto Pearson International Airport to Midway International Airport Flights

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • What's the closest airport to Midway International Airport (MDW)?

    The closest airport to Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.

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