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Key West International Airport to Midway International Airport flight
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Cheap Flights from Key West International Airport to Midway International Airport

Search for flights from Key West 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)
      • EYW17:05
        8h 12m
        1 stop
        MDW00:17
        Key West - Chicago|Thu, Jul 18|United Airlines
        HK$ 1,044HK$ 1,756
        41% OFF
        41% OFF
        HK$ 1,756HK$ 1,044
      • EYW17:05
        8h 12m
        1 stop
        MDW00:17
        Key West - Chicago|Thu, Jul 18|Silver Airways
        HK$ 1,061HK$ 1,756
        40% OFF
        40% OFF
        HK$ 1,756HK$ 1,061
      • EYW13:05
        11h 31m
        1 stop
        MDW23:36
        Key West - Chicago|Fri, Jul 5|United Airlines
        HK$ 1,072HK$ 1,756
        39% OFF
        39% OFF
        HK$ 1,756HK$ 1,072
      • EYW10:00
        9h 48m
        1 stop
        MDW18:48
        Key West - Chicago|Mon, Sep 9|United Airlines
        HK$ 1,206
        HK$ 1,206
      • EYW10:00
        9h 48m
        1 stop
        MDW18:48
        Key West - Chicago|Mon, Sep 9|Silver Airways
        HK$ 1,231
        HK$ 1,231
      • EYW15:20
        19h
        1 stop
        MDW09:20
        Key West - Chicago|Wed, Jul 31|Silver Airways
        HK$ 1,299
        HK$ 1,299
      • EYW09:00
        16h 21m
        1 stop
        MDW00:21
        Key West - Chicago|Sun, Jul 14|United Airlines
        HK$ 1,299
        HK$ 1,299
      • EYW13:05
        11h 34m
        1 stop
        MDW23:39
        Key West - Chicago|Mon, Jul 1|United Airlines
        HK$ 1,303
        HK$ 1,303
      • EYW09:00
        16h 21m
        1 stop
        MDW00:21
        Key West - Chicago|Sun, Jul 14|Silver Airways
        HK$ 1,310
        HK$ 1,310
      • EYW13:05
        11h 34m
        1 stop
        MDW23:39
        Key West - Chicago|Mon, Jul 1|Silver Airways
        HK$ 1,317
        HK$ 1,317
      • EYW13:00
        3h 5m
        Direct
        MDW14:00
        Key West - Chicago|Fri, Jun 28|United Airlines
        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 Key West International Airport to Midway International Airport

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

United Airlines
From HK$ 1,044
Silver Airways
From HK$ 1,061
American Airlines
From HK$ 1,744
Delta Air Lines
From HK$ 2,072
ANA airlines

Find more flights and airlines

Find Cheaper Flights from Key West to Chicago

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

  • Cheapest
    American Airlines
    EYW
    12:05
    6h 34m
    1 transfer
    ORD
    17:39
    Key West International Airport - O'Hare International Airport
    Thu, Jul 4American Airlines
    HK$ 804
  • American Airlines
    EYW
    12:05
    6h 34m
    1 transfer
    ORD
    17:39
    Key West International Airport - O'Hare International Airport
    Thu, Jul 4American Airlines
    HK$ 804
    Find More Flights
Flight Schedule from Key West International Airport to Midway International Airport

Check the schedule for flights from Key West to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL1072

    Delta Air Lines

    07:25

    EYW

    2.0h

    09:23

    ATL

    SMTWTFS
    Search

  2. DL2417

    Delta Air Lines

    11:05

    ATL

    1.9h

    11:57

    MDW

    SMTWTFS

  3. 3M134

    Silver Airways

    09:00

    EYW

    1.3h

    10:15

    TPA

    SMTWTFS
    Search

  4. F93053

    Frontier Airlines

    13:08

    TPA

    1.7h

    14:52

    ATL

    S-T-T--

  5. F92779

    Frontier Airlines

    19:54

    ATL

    1.9h

    20:49

    MDW

    -M-W--S

  6. UA3135

    United Airlines

    10:00

    EYW

    1.3h

    11:15

    TPA

    SMTWTFS
    Search

  7. F93899

    Frontier Airlines

    19:16

    TPA

    2.7h

    20:59

    MDW

    S---T--

  8. 3M135

    Silver Airways

    10:00

    EYW

    1.3h

    11:15

    TPA

    SMTWTFS
    Search

  9. F91185

    Frontier Airlines

    19:16

    TPA

    2.7h

    20:59

    MDW

    -MT--F-

  10. UA3135

    United Airlines

    10:00

    EYW

    1.3h

    11:15

    TPA

    SMTWTFS
    Search

  11. F91185

    Frontier Airlines

    19:16

    TPA

    2.7h

    20:59

    MDW

    -MT--F-

  12. DL1281

    Delta Air Lines

    12:37

    EYW

    1.9h

    14:33

    ATL

    SMTWTFS
    Search

  13. DL2241

    Delta Air Lines

    17:08

    ATL

    1.9h

    18:02

    MDW

    SMTWT-S

  14. 3M137

    Silver Airways

    17:50

    EYW

    1.3h

    19:05

    TPA

    SMTWTFS
    Search

  15. F91185

    Frontier Airlines

    19:16

    TPA

    2.7h

    20:59

    MDW

    -MT--F-

  16. UA3137

    United Airlines

    17:50

    EYW

    1.3h

    19:05

    TPA

    SMTWTFS
    Search

  17. F91185

    Frontier Airlines

    19:16

    TPA

    2.7h

    20:59

    MDW

    -MT--F-

  18. 3M137

    Silver Airways

    17:50

    EYW

    1.3h

    19:05

    TPA

    SMTWTFS
    Search

  19. F93899

    Frontier Airlines

    19:16

    TPA

    2.7h

    20:59

    MDW

    S---T--

  20. DL2168

    Delta Air Lines

    18:16

    EYW

    2.0h

    20:14

    ATL

    SMTWTFS
    Search

  21. DL1076

    Delta Air Lines

    20:45

    ATL

    1.9h

    21:38

    MDW

    SMTWTFS
Find more flights and airlines

Key West International Airport to Midway International Airport Flights Info

Flight distance1,996.61km
Cheapest one-way ticket priceHK$ 1,044

FAQs for Key West 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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