Cheap Flights from Saint Martin/Sint Maarten to Chicago
Cheap Flights from Saint Martin/Sint Maarten to Chicago
Looking for cheap flights from Saint Martin/Sint Maarten to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Saint Martin/Sint Maarten to Chicago vary by season, cabin, and date, but available award flights can start around 14,413–20,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Saint Martin/Sint Maarten to Chicago for specific travel dates.
2026-12-28
SXM - ORD
Economy | 1 Stop | 2 left
From 14,413 Pts + $171.6
2026-12-28
SXM - ORD
Economy | Non stop | 9+ left
From 15,000 Pts + $141.4
2026-12-28
SXM - ORD
Economy | 1 Stop | 9+ left
From 17,500 Pts + $119
2026-12-28
SXM - ORD
Economy | Non stop | 9+ left
From 19,000 Pts + $116.7
2026-12-28
SXM - ORD
Economy | 1 Stop
From 19,500 Pts + $99
2026-12-28
SXM - ORD
Economy | Non stop | 9+ left
From 20,000 Pts + $93.4
Saint Martin/Sint Maarten to Chicago flight facts
Distance
2,204 mi
3,547 km in a straight line
Estimated flight time
about 5h
In the air, for the straight-line distance
Time difference
−2h
Chicago is 2 hours behind Saint Martin/Sint Maarten.
Airports in Saint Martin/Sint Maarten
SXM · Princess Juliana Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Basse Terre - Chicago · Basse Terre is 57 mi from Saint Martin/Sint Maarten
Flights St. Thomas - Chicago · St. Thomas is 124 mi from Saint Martin/Sint Maarten
Flights Saint Martin/Sint Maarten - Grand Rapids · Grand Rapids is 142 mi from Chicago
Premium cabin flights from Saint Martin/Sint Maarten to Chicago
Premium cabin
2026-12-28
SXM - ORD
First | 1 Stop | 1 left
From 130,000 Pts + $99
Premium cabin
2026-12-28
SXM - ORD
Business | 1 Stop | 7 left
From 35,000 Pts + $119
Premium cabin
2026-12-28
SXM - ORD
Business | 1 Stop
From 42,000 Pts + $99
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Saint Martin/Sint Maarten to Chicago depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Saint Martin/Sint Maarten to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Saint Martin/Sint Maarten to Chicago.
Saint Martin/Sint Maarten and Chicago are about 2,204 miles (3,547 km) apart in a straight line.
Flying the 2,204-mile straight-line distance takes about 5h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is 2 hours behind Saint Martin/Sint Maarten.
Departures from Saint Martin/Sint Maarten: Princess Juliana Intl (SXM). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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