Cheap flights from Chicago to Philipsburg

Flight deals from Chicago to Philipsburg

Below you can see the best deals on flights Chicago — Philipsburg for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 25 October, from $288.

Top 10 cheap flights from Chicago to Philipsburg

About the Chicago — Philipsburg flight

Looking for cheap flights from Chicago to Philipsburg? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Philipsburg ticket online at the best price.

The route has direct flights — around 9 flights per week, flights are operated by United Airlines, American Airlines, a nonstop flight takes about 6 h 55 min, the distance between the cities is around 3,526 km.

Planning your trip? You may find our Philipsburg travel guide, how to get from the airport into town and Philipsburg weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

from $262Min. price

MarchCheapest

NovemberPeak season

YesDirect flights

3,526 kmDistance

6 h 55 minTravel time

2Airlines

9 / wkFlights

Below is a calendar of the lowest flight ticket prices for Chicago — Philipsburg by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $262 in March, and the most expensive are around $290 in November. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

Prices by month

Average one-way fares from Chicago to Philipsburg by month. Tickets are usually cheapest in September (around $209) and priciest in February (about $327) — use the table and chart below to pick the best time to fly.

Month	Average price	Level	Month	Average price	Level	Month	Average price	Level
Jan	$309	high	May	$245	medium	Sep	$209	low
Feb	$327	high	Jun	$227	low	Oct	$218	low
Mar	$327	high	Jul	$218	low	Nov	$264	medium
Apr	$273	medium	Aug	$218	low	Dec	$300	high

Some values are estimated based on seasonality.

When to fly

Weather in Philipsburg: it is warmest in September (up to 28 °C on average) and coolest in February (around 26 °C). The driest month is March.

Tickets are usually cheapest in March and most expensive in November. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Philipsburg

Dry and wet days · Philipsburg

Wind speed and direction · Philipsburg

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How to get the best deal on a Chicago — Philipsburg ticket

Book ahead: fares for Chicago — Philipsburg are usually lower 3–8 weeks before departure than at the last minute.
Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
Chicago is served by more than one airport — compare fares and travel time to each before you book.
The cheapest month to fly to Philipsburg is usually March — plan your trip around it if your dates are flexible.
Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Flights on the Chicago — Philipsburg route are operated by 2 airlines; United Airlines runs the most flights (around 67% of all flights). Compare carriers, flight shares and schedules below.

United AirlinesUA
2x/week
WebsiteFleet: 956165M pax/year
- Direct flight ORD → SXM2x/week
66.7%Open →
American AirlinesAA
1x/week
WebsiteFleet: 965211M pax/year
- Direct flight ORD → SXM1x/week
33.3%Open →

Cities and airports on the Chicago — Philipsburg route

Flights Chicago — Philipsburg depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Princess Juliana International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI

United States

About the city How to get there Weather All about the country United States

Arrival

Philipsburg

SXM

Sint Maarten

About the city How to get there Weather All about the country Sint Maarten

Departure airports

O'Hare International AirportORD
About the airport
Chicago Midway International AirportMDW
About the airport
Midway International AirportNOH
About the airport
Chicago Rockford International AirportRFD
About the airport

Arrival airports

Princess Juliana International AirportSXM
About the airport

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Frequently asked questions about the Chicago — Philipsburg flight

How long is the flight from Chicago to Philipsburg?

A nonstop Chicago — Philipsburg flight takes about 6 h 55 min — the distance between the cities is around 3,526 km.

How far is it from Chicago to Philipsburg?

The distance from Chicago to Philipsburg is about 3,526 km, which a nonstop flight covers in around 6 h 55 min.

Are there direct flights from Chicago to Philipsburg?

Yes, there are nonstop flights Chicago — Philipsburg — around 9 flights per week.

Which airlines fly from Chicago to Philipsburg?

Airlines operating Chicago — Philipsburg include United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Philipsburg flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Princess Juliana International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Philipsburg?

The price of a Chicago — Philipsburg ticket depends on your travel date, season and demand: it is usually cheapest to fly in March, and most expensive in November. Tickets typically cost between $262 and $290. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Philipsburg?

Flights Chicago — Philipsburg are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is March. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Philipsburg?

To catch a low fare Chicago — Philipsburg, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually March.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.