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Cheap flights from Chicago (CHI) to Princess Juliana (SXM)

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The best prices from Chicago to Princess Juliana are usually found in September or May, booked 16 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

How to find the cheapest flight from
Chicago (CHI) to Princess Juliana (SXM)

CHI - SXM
Price
$448 - $689
SXM
Temperature
84.2 - 89.6 °F
SXM
Rainfall
1.9 - 6.2 inches

Popular in

December

High demand for flights, 24% potential price rise

Cheapest in

September

Best time to find cheap flights, 15% potential price drop

Round-trip from

$448

From Chicago to Princess Juliana

One-way from

$233

One-way flight from Chicago to Princess Juliana

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to Princess Juliana?

Departing on a Monday is a good option for securing a great price. You can expect to save up to 36% when planning your travel around this day of the week.

What is the cheapest month to fly from Chicago to Princess Juliana?

Due to multiple factors, expect to potentially pay more when booking in February. For low rates, August can be a great choice for travel to Princess Juliana. Flights to Princess Juliana from Chicago in August are about $527 on average during August, but can be found for as low as $211.

When is the cheapest time to fly from Chicago to Princess Juliana (CHI - SXM)?

It’s typically best to fly out from Chicago to Princess Juliana at noon. Doing so could potentially save you 44% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Chicago to Princess Juliana in October, November 2020

The best prices found for CHI to SXM flights for October, November
14 Nov - 21 Nov
$213pp
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
14 Nov - 21 Nov
$214pp
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
7 Nov - 21 Nov
$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

Chicago to Princess Juliana 2020 flight deals

Cheap flights to Princess Juliana from Chicago found for this year
14 Nov - 21 Nov
$213pp
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
14 Nov - 21 Nov
$214pp
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 - 12 Dec
$222pp
ORD
Chicago O'Hare Intl
Multiple 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 Princess Juliana from Chicago

Save time with Chicago to Princess Juliana direct flight deals
9 Jan - 30 Jan
$569pp
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
6 Mar - 20 Mar
$769pp
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
3 Apr - 10 Apr
$999pp
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 Princess Juliana

Late deals on round-trip flights to Princess Juliana from Chicago, departing today and this week
29 Oct - 5 Nov
$894pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 Oct - 5 Nov
$905pp
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
29 Oct - 5 Nov
$907pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SXM
Simpson Bay Princess Juliana
SXM
Simpson Bay Princess Juliana
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

One-way flights to Princess Juliana from Chicago

The cheapest one-way flights from Chicago to Princess Juliana
3:52 am - 9:37 am
Spirit Airlines
3 Stops
27h 45m
ORD - SXM
Spirit Airlines
$233
SmartFares
9:40 am - 9:42 am
Delta
1 Stop
22h 02m
ORD - SXM
Delta
$251
Delta
4:00 am - 11:00 am
United Airlines
Nonstop
5h 00m
ORD - SXM
United Airlines
$401
United

Related info for your journey

Useful info, stats and facts about Chicago to Princess Juliana flights.

Flight FAQs

From Chicago to Princess Juliana

Are flight prices decreasing from Chicago to Princess Juliana due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Princess Juliana for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago to Simpson Bay Princess Juliana to control the spread of COVID-19?

JetBlue and Delta are some of the many airlines that have implemented additional safety measures to control the spread of COVID-19. Some of the new policies that have been implemented to accommodate travelers flying from Chicago to Simpson Bay Princess Juliana are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

Which airlines flying from Chicago to Simpson Bay Princess Juliana have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like American Airlines, Spirit Airlines, and United Airlines flying from Chicago to Simpson Bay Princess Juliana have implemented new flexible cancellation policies.

Can I find flights from Chicago to Princess Juliana for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Princess Juliana for under $300. The cheapest flight booked recently is on Spirit Airlines for just $213, but on average you can expect to pay $264.

Are there nonstop flights from Chicago to Princess Juliana for under $600 on Cheapflights?

Cheapflights has at least 4 direct flights from Chicago to Princess Juliana under $600. A good price for a nonstop flight from Chicago to Princess Juliana is less than $916.

Are there last-minute flights available from Chicago to Princess Juliana for under $900?

There are currently 6+ open flights from Chicago to Princess Juliana within the next 7 days for less than $900.

Is Chicago weather warmer or cooler than Princess Juliana?

You can imagine temperatures to be in the 90 °F range in June. The weather in Princess Juliana is generally hotter than Chicago's. As flight availability is subject to become more limited as peak season approaches it is ideal to book in a timely manner.

How long is the flight from Chicago to Princess Juliana?

Delta and Spirit Airlines can get you from Chicago to Princess Juliana in just under 6h 23m. Your travel time can differ by up to 27m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Chicago to Princess Juliana round-trip?

Spirit Airlines, at $213, was found to be the cheapest airline from Chicago to Princess Juliana. An alternate airline flying to your destination would be JetBlue. Spirit Airlines is priced at 59% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Chicago to Princess Juliana one-way?

For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $70. Users have also found prices from $245 and $264 on Spirit Airlines and Delta, respectively.

Related searches

Flights to Princess Juliana from Chicago
Flights to Chicago Flights to Princess Juliana Flights from Chicago

Rent a Car

Car Rentals at Princess Juliana

Destination information for Princess Juliana

Things to know before you go. Useful info for your trip from Chicago to Princess Juliana
Today's exchange rate
$1 = ƒ1.79
Average temperature for October in Princess Juliana
87.8 °F
Avg rainfall for October in Princess Juliana
6.0 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Simpson Bay

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