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Cheap Flight Deals from Midway International Airport to Princess Juliana International Airport

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

  • One way
  • Round-trip
sortSort: Price (Lowest)
  • Sort: Price (Lowest)
  • Sort: Departure (Earliest)

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

Selected Airlines from Midway International Airport to Princess Juliana International Airport

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

Frontier Airlines
From €116
Southwest Airlines
From €236
Porter Airlines
From €250
Delta Air Lines
From €294
ANA airlines

Find more flights and airlines

Find Cheaper Flights from Chicago to Sint Maarten

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

  • Cheapest
    Spirit Airlines
    ORD
    18:46
    18h 19m
    1 transfer
    SXM
    14:05
    O'Hare International Airport - Princess Juliana International Airport
    Tue, Jul 16Spirit Airlines
    €89
  • Spirit Airlines
    ORD
    18:46
    18h 19m
    1 transfer
    SXM
    14:05
    O'Hare International Airport - Princess Juliana International Airport
    Tue, Jul 16Spirit Airlines
    €89
    Find More Flights
Flight Schedule from Midway International Airport to Princess Juliana International Airport

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

Flight info.
Departure
Arrival
Weekly Schedule
  1. DL1285

    06:00

    MDW

    1.9h

    08:54

    ATL

    S---TFS
  2. DL1894

    09:45

    ATL

    4.0h

    13:45

    SXM

    SMTWTFS
  3. DL1739

    15:47

    MDW

    2.0h

    18:45

    ATL

    S---TFS
  4. DL1894

    09:45

    ATL

    4.0h

    13:45

    SXM

    SMTWTFS
  5. PD2394

    17:15

    MDW

    1.7h

    19:57

    YTZ

    SMTWT-S
  6. WS2652

    08:30

    YYZ

    4.7h

    13:12

    SXM

    ---W--S
  7. DL2307

    18:50

    MDW

    1.8h

    21:40

    ATL

    S---T-S
  8. DL1894

    09:45

    ATL

    4.0h

    13:45

    SXM

    SMTWTFS
  9. WN3618

    19:45

    MDW

    2.9h

    23:40

    FLL

    -MT----
  10. NK100

    11:00

    FLL

    3.1h

    14:09

    SXM

    S-T-TF-
  11. F91458

    20:56

    MDW

    2.9h

    00:47

    MCO

    S----F-
  12. F92250

    08:01

    MCO

    3.1h

    11:05

    SJU

    SMTW-FS
  13. F9244

    13:33

    SJU

    1.0h

    14:31

    SXM

    S---T--
  14. F91458

    20:56

    MDW

    2.9h

    00:47

    MCO

    S----F-
  15. AA1896

    05:00

    MCO

    1.8h

    06:48

    CLT

    SMTWTFS
  16. AA2478

    09:00

    CLT

    3.8h

    12:50

    SXM

    SMTWTFS
  17. F93854

    21:04

    MDW

    2.7h

    00:44

    MCO

    ---W--S
  18. F93506

    10:57

    MCO

    3.0h

    13:55

    SJU

    -MT-T--
  19. F9244

    13:33

    SJU

    1.0h

    14:31

    SXM

    S---T--
  20. F93854

    21:04

    MDW

    2.7h

    00:44

    MCO

    ---W--S
  21. F92250

    08:01

    MCO

    3.1h

    11:05

    SJU

    SMTW-FS
  22. F9244

    13:33

    SJU

    1.0h

    14:31

    SXM

    S---T--
  23. F93854

    21:04

    MDW

    2.7h

    00:44

    MCO

    ---W--S
  24. F91824

    05:01

    MCO

    2.9h

    07:54

    SJU

    ---WT-S
  25. F9244

    13:33

    SJU

    1.0h

    14:31

    SXM

    S---T--

Midway International Airport to Princess Juliana International Airport Flights Info

Flight distance3,528.08km
Cheapest one-way ticket price€182
Cheapest return ticket price€601