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

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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 $100 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Aug 22 - Mon, Aug 25
ORD
Chicago
MCO
Orlando
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Aug 22 from Chicago to Orlando, returning Mon, Aug 25, priced at $100 just found
Spirit Airlines
Sun, Oct 5 - Tue, Oct 7
ORD
Chicago
MCO
Orlando
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Oct 5 from Chicago to Orlando, returning Tue, Oct 7, priced at $100 just found
Frontier Airlines
Mon, Sep 22 - Fri, Sep 26
MDW
Chicago
MCO
Orlando
$101 Roundtrip, just found
$101
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Sep 22 from Chicago to Orlando, returning Fri, Sep 26, priced at $101 just found
Southwest Airlines
Wed, Aug 27 - Sat, Aug 30
ORD
Chicago
MCO
Orlando
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Chicago to Orlando, returning Sat, Aug 30, priced at $157 found 1 hour ago
Alaska Airlines
Tue, Oct 7 - Wed, Oct 8
ORD
Chicago
LAS
Las Vegas
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Tue, Oct 7 from Chicago to Las Vegas, returning Wed, Oct 8, priced at $178 found 2 hours ago
Hawaiian Airlines
Tue, Nov 11 - Wed, Nov 19
ORD
Chicago
LAS
Las Vegas
$178 Roundtrip, found 5 days ago
$178
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Tue, Nov 11 from Chicago to Las Vegas, returning Wed, Nov 19, priced at $178 found 5 days 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 $501
SXM
Princess Juliana Intl.
Cheapest
Flights from $501
Select flight to Clayton J. Lloyd Intl. AXA. Flights from $823
AXA
Clayton J. Lloyd Intl.
Flights from $823

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