Cheap flights from Chicago to St. Maarten from $184

The cheapest month to fly to St. Maarten from Chicago is in February. Flight prices, which tend to average around $565, are often lower during this time because this is during the off-season. If you’re not able to fly to St. Maarten in February, then January is your next best option. Flight prices from Chicago to St. Maarten during January average around $595.

According to our data, Saturday is the cheapest day to fly to St. Maarten from Chicago. The lowest ticket price found for a Saturday departure recently was $782. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to St. Maarten is Thursday, with ticket prices averaging around $854.

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago - St. Maarten flight prices

You are more likely to see cheaper flights to St. Maarten from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to St. Maarten for around $695 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to St. Maarten from Chicago for as low as $457 on momondo.

There are 4 cabin classes available to choose from on Chicago to St. Maarten flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 38% on your flight if you consider stops on a Chicago to St. Maarten flight.

Air Canada, Southwest, and American Airlines are the most popular carriers operating from Chicago to St. Maarten

American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to St. Maarten from Chicago according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to St. Maarten. Keep in mind that there are 4 different airlines that fly to St. Maarten on a routine basis, so you have a few additional options to choose from.

Historically, on average around 25% of flights between Chicago and St. Maarten have experienced a delay on any given week. The average delay length over the past 12 months has been 105 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.