Cheap flights from Chicago (CHI) to St. Maarten

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How to find the cheapest flight from
Chicago (CHI) to St. Maarten

All the information you need to plan the best CHI to SXM flight in 2021: compare Chicago to St. Maarten flight prices with the expected peak season, weather and rainfall in St. Maarten.
How far in advance should I book a flight from Chicago to St. Maarten?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 38 days in advance, which can save you up to 14% on flights from Chicago to St. Maarten compared to booking the week you need them. Waiting 38 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $603. For sooner than that we have options available in the next 3 days from $653.

What is the cheapest month to fly from Chicago to St. Maarten?

September can be a great time to fly to St. Maarten from Chicago with a flight ticket averaging about $578. Cheapflights users have found deals in the month of September for as cheap as $304. The most expensive prices can be found in the month of December.

When is the cheapest time to fly from Chicago to St. Maarten (CHI - SX)?

When flying from Chicago to St. Maarten, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Chicago to St. Maarten in November, December 2021

The best prices found for CHI to St. Maarten flights for November, December
11 Dec - 25 Dec
$242pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Dec - 11 Dec
$243pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
11 Dec - 25 Dec
$246pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to St. Maarten 2022 flight deals

Cheap flights to St. Maarten from Chicago found for this year
11 Dec - 25 Dec
$242pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Dec - 11 Dec
$243pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
11 Dec - 25 Dec
$246pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to St. Maarten from Chicago

Save time with Chicago to St. Maarten direct flight deals
15 Jan - 22 Jan
$799pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
11 Dec - 25 Dec
$849pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
16 Apr - 23 Apr
$889pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to St. Maarten

Late deals on round-trip flights to St. Maarten from Chicago, departing today and this week
11 Dec - 25 Dec
$242pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
11 Dec - 25 Dec
$246pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
11 Dec - 25 Dec
$300pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to St. Maarten from Chicago

The cheapest one-way flights from Chicago to St. Maarten
1:24 am - 10:49 am
Frontier
1 Stop
7h 25m
ORD - SXM
Frontier
$77
SmartFares
4:45 pm - 9:50 am
Spirit Airlines
3 Stops
39h 05m
ORD - SXM
Spirit Airlines
$272
Kiwi.com
12:30 am - 10:45 am
JetBlue
1 Stop
8h 15m
ORD - SXM
JetBlue

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">St. Maarten</span> flights.

Flight FAQs

From Chicago to St. Maarten

Which airlines flying from Chicago to St. Maarten have flexible cancellations due to COVID-19?

American Airlines, Spirit Airlines, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to St. Maarten for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to St. Maarten for under $300. The cheapest flight booked recently is on Spirit Airlines for just $219, but on average you can expect to pay $247.

Are there nonstop flights from Chicago to St. Maarten for under $800 on Cheapflights?

Cheapflights has at least 16 direct flights from Chicago to St. Maarten under $800. A good price for a nonstop flight from Chicago to St. Maarten is less than $1,271.

Are there last-minute flights available from Chicago to St. Maarten for under $300?

There are currently 20+ open flights from Chicago to St. Maarten within the next 7 days for less than $300.

What are the cheapest airlines to fly from Chicago to St. Maarten one-way?

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $74. Frontier flights start at $77 while deals on JetBlue start at $113 one-way.

What are the most popular airlines that fly from Chicago to St. Maarten?

Consider American Airlines, Air Canada or JetBlue when booking your flight. These represent the most popular airlines when flying from Chicago to St. Maarten.

What are the cheapest flights from Chicago to St. Maarten?

Looking at all options, your cheapest flight can be booked for $86. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $219 on average our data indicates $673 when flying from Chicago to St. Maarten.

Related searches

Flights to St. Maarten from Chicago
Flights to Chicago Flights to St. Maarten Flights from Chicago

Rent a Car

Car Rentals in St. Maarten

COVID Restrictions

View COVID Travel Restrictions for St. Maarten

Do I need a COVID test to fly to St. Maarten from Chicago?

Information is based on travel restrictions from Chicago to St. Maarten

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter St. Maarten.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 for RT-PCR (NAAT) and 48 Antigen (quick-test) hours before departing to St. Maarten.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering St. Maarten.

Documents
Electronic Health Authorization System (EHAS) Form - Processing of this application can take up to 12 hours.

Health Insurance - Travelers are required to pay for health insurance when applying for their travel registration form


Do I need a test to fly back to Chicago from St. Maarten?

Returning to Chicago from St. Maarten

COVID-19 testing requirements
Visitors from St. Maarten must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from St. Maarten are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for St. Maarten

Destination information for St. Maarten

Things to know before you go - useful duration and weather info for your trip from Chicago to St. Maarten.
Today's exchange rate
$1 = ƒ1.79

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing

Simpson Bay Princess Juliana (SXM)

Top 5 airlines flying from Chicago to St. Maarten

The chart below displays the airlines Cheapflights users traveling from Chicago to St. Maarten choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
JetBlue
$190 $332 No cancel fee 62%
Spirit Airlines
$203 $388 No cancel fee 65%
American Airlines
$275 $632 No cancel fee 71%
Delta
$277 $731 No cancel fee N/A
United Airlines
$308 $806 No cancel fee 69%
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