Find Cheap Flights from Chicago to Sint Maarten (CHI - SXM)

Flights overview

Useful information for finding cheap flights from Chicago to Sint Maarten and booking your next trip

Cheapest round-trip flights	$272	Spirit 1 stop 18 hr Sat, May 2 — Sat, May 9	The cheapest round-trip flight from Chicago to Sint Maarten is currently $272
Cheapest one-way flight	$143	Air Canada 1 stop 20 hr Wed, Jun 3	The cheapest one-way flight from Chicago to Sint Maarten is currently $143
Cheapest nonstop flights	$1,020	United Nonstop 6 hr Sat, Apr 18 — Sat, Apr 25	The cheapest nonstop round-trip flight from Chicago to Sint Maarten is currently $1,020
Last-minute weekend getaway	$435	Air Canada 1 stop 22 hr Thu, Apr 16 — Mon, Apr 20	The cheapest last-minute weekend getaway from Chicago to Sint Maarten is currently $435
Cheapest business class flights	$1,073	COPA 1 stop 20 hr Thu, May 28 — Wed, Jun 3	The cheapest business class round-trip flight from Chicago to Sint Maarten is currently $1,073

Fastest flight	5 hr 14 min	The fastest nonstop flight from Chicago to Sint Maarten takes 5 hr 14 min
Nonstop flights	Some days	There are direct flights on this route 1 days a week: Sat.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Sint Maarten is typically January. The most expensive month to fly is typically September.

January Cheapest	Typical prices: $270–485
September Most expensive	Typical prices: $495–640

Popular airlines from Chicago to Sint Maarten

Southwest

from $520

Typical price: $590–900

873 weekly connecting flights

MDW, ORD - SXM Every day
American

from $665

Typical price: $560–940

477 weekly connecting flights

ORD - SXM Every day
Delta

from $665

Typical price: $610–1,350

256 weekly connecting flights

MDW, ORD - SXM Every day
United

Nonstop

from $665

Typical price: $580–1,250

1 weekly nonstop flight

ORD - SXM Every Sat

86 weekly connecting flights

ORD - SXM Every day
JetBlue

from $705

Typical price: $640–1,750

21 weekly connecting flights

ORD - SXM Every day
Spirit

from $272

Typical price: $325–680

15 weekly connecting flights

ORD - SXM Every Tue, Wed, Thu, Fri, Sat, Sun

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 25 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 24 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Sint Maarten

Princess Juliana International Airport (SXM)

Sint Maarten Sint Maarten 20 min 3 mi
Grand Case-Espérance Airport (SFG)

Saint Martin St. Martin 19 min 4 mi

Frequently asked questions about flying from Chicago to Sint Maarten

The cheapest flights from Chicago to Sint Maarten are usually in January. Typical ticket prices in January range from $270 to $485.

The cheapest round-trip flight from Chicago to Sint Maarten recently found on Google Flights was with Spirit from $272. The cheapest one-way flight was with Air Canada from $143.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Sint Maarten is $520, flying from May 11 to May 20.
The cheapest American flight from Chicago to Sint Maarten is $665, flying from Jul 4 to Jul 10.
The cheapest Delta flight from Chicago to Sint Maarten is $665, flying from May 18 to May 27.
The cheapest United flight from Chicago to Sint Maarten is $665, flying from May 28 to Jun 3.
The cheapest JetBlue flight from Chicago to Sint Maarten is $705, flying from Jun 12 to Jun 20.
The cheapest Spirit flight from Chicago to Sint Maarten is $272, flying from May 2 to May 9.

The cheapest round-trip flight from Chicago to Sint Maarten starts at $272 from Sat, May 2 to Sat, May 9. The cheapest one-way flight starts at $143 and departs on Wed, Jun 3.

5 hr 14 min is the shortest flight time from Chicago to Sint Maarten.

The climate is tropical, with warm temperatures year-round and rain possible at any time. Peak beach season is Dec–May. The well-known St. Maarten Regatta (Mar) attracts competitors from all over the world. Calypso music provides the soundtrack to the annual Carnival parades (Apr). St. Maarten's Day (Nov 11) is a traditional Dutch Christian festival in honor of St. Martin of Tours. Official hurricane season is Jun–Nov.

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Sint Maarten.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Chicago to Sint Maarten really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Sint Maarten.

In terms of nonstop flights, United is the most popular. United offers 1 nonstop flights and 86 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM) .

In terms of flights, Southwest is the most popular. Southwest offers 873 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM) .

Other popular airlines flying from Chicago to Sint Maarten are:

American offers 477 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM) .
Delta offers 256 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM) .
JetBlue offers 21 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM) .
Spirit offers 15 connecting flights per week. Spirit flies from Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM) .

The number of connecting flights refers to distinct flights with at least one stop between Chicago and Sint Maarten.

The cheapest round-trip flight from Chicago to Sint Maarten recently found on Google Flights was with Spirit from $272. The cheapest one-way flight was with Air Canada from $143.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Sint Maarten is $520, flying from May 11 to May 20.
The cheapest American flight from Chicago to Sint Maarten is $665, flying from Jul 4 to Jul 10.
The cheapest Delta flight from Chicago to Sint Maarten is $665, flying from May 18 to May 27.
The cheapest United flight from Chicago to Sint Maarten is $665, flying from May 28 to Jun 3.
The cheapest JetBlue flight from Chicago to Sint Maarten is $705, flying from Jun 12 to Jun 20.
The cheapest Spirit flight from Chicago to Sint Maarten is $272, flying from May 2 to May 9.

United flies direct from Chicago to Sint Maarten.

There are 1 United direct flights from Chicago to Sint Maarten per week. Flights are available on Saturday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Chicago and Sint Maarten at price $435 is offered by Air Canada from Thu, Apr 16 to Mon, Apr 20.

United flies direct from Chicago to Sint Maarten.

There are 1 United direct flights from Chicago to Sint Maarten per week. Flights are available on Saturday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

Direct flights from Chicago to Sint Maarten are only available on Saturday.

The cheapest direct (nonstop) round-trip flights between Chicago and Sint Maarten start at $1,020 from Sat, Apr 18 to Sat, Apr 25 with United.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Sint Maarten, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Chicago and Sint Maarten start at $1,073 from Thu, May 28 to Wed, Jun 3 with COPA.

The cheapest economy class round-trip flights between Chicago and Sint Maarten start at $272 from Sat, May 2 to Sat, May 9.

To book business class trips from Chicago to Sint Maarten, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Chicago and Sint Maarten starts at $435 from Thu, Apr 16 to Mon, Apr 20 with Air Canada.

The cheapest last-minute deal between Chicago and Sint Maarten at price $435 is offered by Air Canada from Thu, Apr 16 to Mon, Apr 20.

To find last-minute flight deals from Chicago to Sint Maarten, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.