Cheap flights from Chicago to Saint Martin

View AU$119 flight on Tue, 16 Sep. 2025Opens in a new window

Popular airlines from Chicago to Saint Martin

  • American Airlines

    American Airlines

  • Delta

    Delta

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Cheap Flights from Chicago (CHI) to Saint Martin (SXM)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 20 Sep. - Sat, 27 Sep.
ORD
Chicago
MCO
Orlando
AU$238 Return, found 12 hours ago
AU$238
Return
found 12 hours ago
Select American Airlines flight, departing Sat, 20 Sep. from Chicago to Orlando, returning Sat, 27 Sep., priced at AU$238 found 12 hours ago
Delta
Sat, 20 Sep. - Sat, 27 Sep.
MDW
Chicago
MCO
Orlando
AU$299 Return, found 12 hours ago
AU$299
Return
found 12 hours ago
Select Delta flight, departing Sat, 20 Sep. from Chicago to Orlando, returning Sat, 27 Sep., priced at AU$299 found 12 hours ago
Delta
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
MCO
Orlando
AU$299 Return, found 12 hours ago
AU$299
Return
found 12 hours ago
Select Delta flight, departing Wed, 10 Sep. from Chicago to Orlando, returning Wed, 17 Sep., priced at AU$299 found 12 hours ago
United
Sat, 20 Sep. - Sat, 27 Sep.
ORD
Chicago
MCO
Orlando
AU$345 Return, found 12 hours ago
AU$345
Return
found 12 hours ago
Select United flight, departing Sat, 20 Sep. from Chicago to Orlando, returning Sat, 27 Sep., priced at AU$345 found 12 hours ago
Alaska Airlines
Sat, 6 Sep. - Fri, 12 Sep.
ORD
Chicago
LAX
Los Angeles
AU$346 Return, found 5 days ago
AU$346
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 6 Sep. from Chicago to Los Angeles, returning Fri, 12 Sep., priced at AU$346 found 5 days ago
Hawaiian Airlines
Fri, 8 Aug. - Wed, 13 Aug.
ORD
Chicago
LAX
Los Angeles
AU$499 Return, found 2 days ago
AU$499
Return
found 2 days ago
Select Hawaiian Airlines flight, departing Fri, 8 Aug. from Chicago to Los Angeles, returning Wed, 13 Aug., priced at AU$499 found 2 days ago

Find the cheapest month to fly from Chicago (CHI) to Simpson Bay (SXM)

April is typically the cheapest month to fly

From AU$507 - AU$1,123 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.