What is the cheapest month to book a flight from St. Maarten to Chicago?

Currently, August is the cheapest month in which you can book a flight from St. Maarten to Chicago (average of $245). Flying from St. Maarten to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

Travelers seeking maximum savings on their St. Maarten to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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

Looking for the cheapest flight from St. Maarten to Chicago? While on average our users pay $610, our data indicates the cheapest price to be $538. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $344.

What is the cheapest day to fly round-trip from St. Maarten to Chicago?

Leaving on a Sunday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 63% on the overall cost on flights from St. Maarten to Chicago.

Can I find deals for flights from St. Maarten to Chicago that include hotel bookings?

Yes. In addition to deals on St. Maarten to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from St. Maarten to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. Maarten to Chicago.

Can I find deals for business class flights from St. Maarten to Chicago?

Yes. Cheapflights offers flight deals from St. Maarten to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$1,081+ Flights from St. Maarten to Chicago - Compare & Save Big

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Cheap flight deals from St. Maarten to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Good one-way deal	$554 or less

Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.

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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.

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Price to beat on a one-way flight from St. Maarten to Chicago (CHI).

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Cheapest flights from St. Maarten to Chicago
Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

Sat 12/63:35 pmSXM - ORD

1 stop8h 07mAmerican Airlines

Sat 12/136:45 pmORD - SXM

1 stop17h 30mAmerican Airlines

Deal found 4/25

$647

Fri 4/256:26 pmSXM - ORD

1 stop17h 32mMultiple Airlines

Tue 4/296:20 amORD - SXM

2 stops28h 01mMultiple Airlines

Deal found 4/25

$762

Sat 4/263:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Sat 5/35:36 amORD - SXM

1 stop7h 24mSpirit Airlines

Deal found 4/25

$794

Sat 12/62:46 pmSXM - ORD

Nonstop5h 54mUnited Airlines

Sat 12/138:45 amORD - SXM

Nonstop5h 07mUnited Airlines

Deal found 4/25

$1,103

Sat 4/261:46 pmSXM - MDW

1 stop9h 36mDelta

Sat 5/36:04 amMDW - SXM

1 stop7h 01mDelta

Deal found 4/25

$1,894

Last-minute flights from St. Maarten to Chicago
Discover last-minute flight deals from St. Maarten to Chicago. Data last updated April 25, 2025 and is based on user searches.

Fri 4/256:26 pmSXM - ORD

1 stop17h 32mMultiple Airlines

Tue 4/296:20 amORD - SXM

2 stops28h 01mMultiple Airlines

Deal found 4/25

$762

Sat 4/263:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Sat 5/35:36 amORD - SXM

1 stop7h 24mSpirit Airlines

Deal found 4/25

$794

Sat 4/261:46 pmSXM - MDW

1 stop9h 36mDelta

Sat 5/36:04 amMDW - SXM

1 stop7h 01mDelta

Deal found 4/25

$1,894

Best time to book a flight from St. Maarten to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Maarten with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from St. Maarten to Chicago

What is the cheapest time of day to fly from SX to CHI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from St. Maarten to Chicago as you normally would.

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Related info for your journey

What are the cheapest flights from St. Maarten to Chicago?
Looking for the cheapest flight from St. Maarten to Chicago? While on average our users pay $610, our data indicates the cheapest price to be $538. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $344.
Can I find deals for flights from St. Maarten to Chicago that include hotel bookings?
Yes. In addition to deals on St. Maarten to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from St. Maarten to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. Maarten to Chicago.
Can I find deals for business class flights from St. Maarten to Chicago?
Yes. Cheapflights offers flight deals from St. Maarten to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from St. Maarten to Chicago?
Currently, August is the cheapest month in which you can book a flight from St. Maarten to Chicago (average of $245). Flying from St. Maarten to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top airline flying from St. Maarten to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$554	Average$755	FlexibilityNo cancel fee	On-time71%

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$647+ Cheap flights from St. Maarten to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from St. Maarten to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from St. Maarten to Chicago

Keep the following information in mind while searching for St. Maarten to Chicago flight deals. Data was last updated April 25, 2025.

Most accurate provider

Most trusted provider

Good one-way deal

Find flight deals from St. Maarten to Chicago

Cheapest flights from St. Maarten to ChicagoExplore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

Best time to book a flight from St. Maarten to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Maarten with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from St. Maarten to Chicago

What is the cheapest time of day to fly from SX to CHI?

Find hourly flight availability from St. Maarten to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Related info for your journey

Find useful and relevant information for your journey from St. Maarten to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

Can I find deals for flights from St. Maarten to Chicago that include hotel bookings?

How can I find direct flights from St. Maarten to Chicago?

Can I find deals for business class flights from St. Maarten to Chicago?

What is the cheapest month to book a flight from St. Maarten to Chicago?

Traveling to a place near St. Maarten?

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Alternative routes for St. Maarten to Chicago

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Top airline flying from St. Maarten to Chicago

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Cheapest flights from St. Maarten to Chicago
Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.