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
$180 - $640
Route
Depart
Return
Price
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
1 stop9h 45m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 5/18
2 stops20h 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
Wed 5/22
1 stop7h 44m
Simpson Bay Princess Juliana
Wed 5/29
1 stop27h 56m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 5/18
2 stops18h 54m
Simpson Bay Princess Juliana
Sat 5/25
1 stop9h 45m
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 stop27h 56m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/21
1 stop15h 50m
Simpson Bay Princess Juliana
Tue 5/28
1 stop8h 17m
Chicago MidwaySimpson Bay Princess Juliana
MDW - SXM
MDWSXM
Chicago Midway
Tue 5/21
1 stop6h 40m
Simpson Bay Princess Juliana
Tue 5/28
1 stop17h 45m
Chicago O'Hare IntlSimpson Bay Princess Juliana
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 5/18
1 stop14h 15m
Simpson Bay Princess Juliana
Sat 5/25
Nonstop5h 44m
No data available for this route at this time. Please check back soon.
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
Boarding
Entertainment
Food
Crew
Comfort
Overall
Reviews
Terrible flight crew that skipped our row for service multiple times.
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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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