When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 24 days in advance, which can save you up to 105% on flights from Chicago to St. Maarten compared to booking the week you need them. Waiting 24 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $825. For sooner than that we have options available in the next 3 days from $1,267.
September can be a great time to fly to St. Maarten from Chicago with a flight ticket averaging about $858. Cheapflights users have found deals in the month of September for as cheap as $484. The most expensive prices can be found in the month of March.
When flying from Chicago to St. Maarten, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$179 - $566
Route
Depart
Return
Price
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Sat 5/18
1 stop16h 59m
Simpson Bay Princess Juliana
Sat 5/25
1 stop15h 40m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 5/18
1 stop20h 11m
Simpson Bay Princess Juliana
Sat 5/25
1 stop9h 44m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 5/18
1 stop20h 11m
Simpson Bay Princess Juliana
Sat 5/25
2 stops21h 10m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Sat 5/18
2 stops30h 14m
Simpson Bay Princess Juliana
Sat 5/25
1 stop15h 40m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Thu 5/30
1 stop18h 04m
Simpson Bay Princess Juliana
Sun 6/2
1 stop9h 54m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Thu 5/30
2 stops18h 23m
Simpson Bay Princess Juliana
Sun 6/2
1 stop9h 54m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 5/15
1 stop7h 44m
Simpson Bay Princess Juliana
Mon 5/20
1 stop20h 11m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Tue 5/28
1 stop6h 40m
Simpson Bay Princess Juliana
Thu 6/6
1 stop7h 51m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 7/23
1 stop15h 48m
Simpson Bay Princess Juliana
Tue 7/30
1 stop22h 21m
No data available for this route at this time. Please check back soon.
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Comfort
Food
Crew
Boarding
Entertainment
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Cheapflights makes it easy to find Chicago to St. Maarten flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
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Certainly. Search results for flights to St. Maarten from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
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