Cheap flights from Chicago to St. Maarten from $199
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to St. Maarten departing on 6/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines flights from Chicago to St. Maarten
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Delta flights from Chicago to St. Maarten
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How to get the cheapest flight ticket from Chicago to St. Maarten
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to St. Maarten?
The cheapest month to fly to St. Maarten from Chicago is in September. Flight prices, which tend to average around $607, are often lower during this time because this is during the off-season. If you’re not able to fly to St. Maarten in September, then October is your next best option. Flight prices from Chicago to St. Maarten during October average around $656.
What is the cheapest day to depart on your flight to St. Maarten?
According to our data, Monday is the cheapest day to fly to St. Maarten from Chicago. The lowest ticket price found for a Monday departure recently was $636. 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 Saturday, with ticket prices averaging around $931.
What is the cheapest time of day to depart on your flight to St. Maarten?
At noon is the cheapest time of day to fly from Chicago to St. Maarten when you can find flight prices for as low as $417. Flying to St. Maarten at noon is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to St. Maarten is in the morning when prices are around $913.
What is the cheapest Chicago to St. Maarten flight route?
Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago - St. Maarten flight prices
How far in advance should I book a flight to St. Maarten?
You are more likely to see cheaper flights to St. Maarten from Chicago when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to St. Maarten for around $746 when searching 6 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 $606 on momondo.
What cabin class options are available on Chicago to St. Maarten flights?
There are 3 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.
What is the cheapest airline that flies from Chicago to St. Maarten?
Spirit Airlines, American Airlines, and Delta are the most popular carriers operating from Chicago to St. Maarten
What airlines fly to St. Maarten?
American Airlines, United Airlines and Spirit Airlines 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 49% 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.
Cheap Chicago to St. Maarten flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to St. Maarten
When did momondo last update prices for flights from Chicago to St. Maarten?
Prices for flights from Chicago to St. Maarten were last updated today.
How many operators does momondo search for flights from Chicago to St. Maarten?
As of May 2025, there are 4 operators available to choose from for flights from Chicago to St. Maarten.
How old do you have to be to fly from Chicago to St. Maarten?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to St. Maarten.
What documentation or ID do you need to fly to St. Maarten?
The travel and health documents required for your trip to St. Maarten can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at St. Maarten. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to St. Maarten?
Based on momondo bookings for flights between Chicago and St. Maarten, the leading plane model is Boeing 737-700, making up 100.00% of the total bookings.
Best airlines flying from Chicago to St. Maarten
Compare and see reviews for airlines that fly from Chicago to St. Maarten with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $325 | Free Cancellation | Rating 6.3 7,963 reviews | |||
| PriceFrom $554 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $606 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $647 | Free Cancellation | Rating 7.4 8,696 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to St. Maarten?
Finding the right flight to St. Maarten from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to St. Maarten quick and easy, saving you time and money.
Can I find flights from Chicago to St. Maarten with flexible booking policies on momondo?
momondo does allow users to show only those flights to St. Maarten from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to St. Maarten?
momondo helps you find the best flight between Chicago and St. Maarten by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to St. Maarten right now. Can momondo alert me if prices change?
If you are simply researching potential flights to St. Maarten, momondo offers a useful price alert feature which will track prices for flights to St. Maarten from Chicago and alert you when they change.