Flights to Saint Martin from Chicago - $44

View $44 flight on Tue, Aug 19, 2025Opens in a new window

Popular airlines from Chicago to Saint Martin

  • JetBlue Airways

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  • Delta

    Delta

  • American Airlines

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  • United

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  • Spirit Airlines

    Spirit Airlines

  • Air Canada

    Air Canada

  • Copa

    Copa

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

Prices were available within the past 7 days and start at $44 for one-way flights and $88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Aug 19 - Wed, Aug 20
ORD
Chicago
LAS
Las Vegas
$88 Roundtrip, found 1 hour ago
$88
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Aug 19 from Chicago to Las Vegas, returning Wed, Aug 20, priced at $88 found 1 hour ago
Frontier Airlines
Thu, Sep 25 - Mon, Sep 29
ORD
Chicago
MCO
Orlando
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Sep 25 from Chicago to Orlando, returning Mon, Sep 29, priced at $100 just found
Frontier Airlines
Mon, Sep 29 - Sat, Oct 4
MDW
Chicago
MCO
Orlando
$101 Roundtrip, just found
$101
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Sep 29 from Chicago to Orlando, returning Sat, Oct 4, priced at $101 just found
Southwest Airlines
Sat, Oct 25 - Sat, Nov 1
ORD
Chicago
MCO
Orlando
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Oct 25 from Chicago to Orlando, returning Sat, Nov 1, priced at $157 just found
Alaska Airlines
Tue, Oct 21 - Thu, Oct 30
ORD
Chicago
LAS
Las Vegas
$178 Roundtrip, found 1 hour ago
$178
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Tue, Oct 21 from Chicago to Las Vegas, returning Thu, Oct 30, priced at $178 found 1 hour ago
Hawaiian Airlines
Tue, Dec 9 - Wed, Dec 10
ORD
Chicago
LAS
Las Vegas
$178 Roundtrip, found 4 hours ago
$178
Roundtrip
found 4 hours ago
Select Hawaiian Airlines flight, departing Tue, Dec 9 from Chicago to Las Vegas, returning Wed, Dec 10, priced at $178 found 4 hours ago

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

April is typically the cheapest month to fly

From $330 - $732 per traveler.

Graph displaying average flight prices per month

Alternative airports

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Princess Juliana Intl. SXM. Cheapest option available. Flights from $701
SXM
Princess Juliana Intl.
Cheapest
Flights from $701
Select flight to Clayton J. Lloyd Intl. AXA. Flights from $823
AXA
Clayton J. Lloyd Intl.
Flights from $823

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