Cheap flights from Chicago to Saint Martin

View AU$105 flight on Fri, 17 Oct. 2025Opens in a new window

Popular airlines from Chicago to Saint Martin

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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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.

United
Fri, 17 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$274 Return, found 15 hours ago
AU$274
Return
found 15 hours ago
Select United flight, departing Fri, 17 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$274 found 15 hours ago
Air Canada
Fri, 5 Sep. - Thu, 18 Sep.
ORD
Chicago
YYZ
Toronto
AU$287 Return, found 18 hours ago
AU$287
Return
found 18 hours ago
Select Air Canada flight, departing Fri, 5 Sep. from Chicago to Toronto, returning Thu, 18 Sep., priced at AU$287 found 18 hours ago
American Airlines
Fri, 17 Oct. - Mon, 20 Oct.
ORD
Chicago
YYZ
Toronto
AU$323 Return, found 15 hours ago
AU$323
Return
found 15 hours ago
Select American Airlines flight, departing Fri, 17 Oct. from Chicago to Toronto, returning Mon, 20 Oct., priced at AU$323 found 15 hours ago
Delta
Wed, 10 Sep. - Wed, 17 Sep.
MDW
Chicago
YYZ
Toronto
AU$366 Return, found 2 days ago
AU$366
Return
found 2 days ago
Select Delta flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Wed, 17 Sep., priced at AU$366 found 2 days ago
Delta
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
YYZ
Toronto
AU$366 Return, found 2 days ago
AU$366
Return
found 2 days ago
Select Delta flight, departing Wed, 10 Sep. from Chicago to Toronto, returning Wed, 17 Sep., priced at AU$366 found 2 days ago
WestJet
Wed, 20 Aug. - Sun, 31 Aug.
ORD
Chicago
YYZ
Toronto
AU$501 Return, found 14 hours ago
AU$501
Return
found 14 hours ago
Select WestJet flight, departing Wed, 20 Aug. from Chicago to Toronto, returning Sun, 31 Aug., priced at AU$501 found 14 hours 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.