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Cheap flight deals from Sint Maarten to Chicago Starting at $263

Whether you’re going for a one-way or round-trip to Chicago, we’ve got you covered! Check out these different flight options from Sint Maarten below.

  • One way
  • Round-trip
      • Cheapest nonstop
        SXM01:16 pm
        5h 54m
        Nonstop
        ORD06:10 pm
        Sun, Mar 9|Sint Maarten - Chicago|United Airlines
        $405$568
        28% OFF
        28% OFF
        $568$405

        Choose United Airlines flights from Sint Maarten to Chicago. The one-way direct flight with United Airlines departs from Princess Juliana International Airport on Sun, Mar 9, arriving at O'Hare International Airport. One-way Prices start from $405 including taxes and charges.

      • SXM02:46 pm
        5h 54m
        Nonstop
        ORD06:40 pm
        Sun, Mar 2|Sint Maarten - Chicago|United Airlines
        $426$568
        25% OFF
        25% OFF
        $568$426

        Choose United Airlines flights from Sint Maarten to Chicago. The one-way direct flight with United Airlines departs from Princess Juliana International Airport on Sun, Mar 2, arriving at O'Hare International Airport. One-way Prices start from $426 including taxes and charges.

      • SXM02:53 pm
        18h 56m
        1 stop
        ORD07:49 am
        Thu, Jan 16|Sint Maarten - Chicago|United Airlines
        $263$568
        54% OFF
        54% OFF
        $568$263

        Choose United Airlines flights from Sint Maarten to Chicago. The one-way connecting flight with United Airlines departs from Princess Juliana International Airport on Thu, Jan 16, arriving at O'Hare International Airport. One-way Prices start from $263 including taxes and charges.

      • SXM04:50 pm
        19h 5m
        1 stop
        ORD09:55 am
        Fri, Jan 31|Sint Maarten - Chicago|Jetblue Airways
        $278
        $278

        Choose Jetblue Airways flights from Sint Maarten to Chicago. The one-way connecting flight with Jetblue Airways departs from Princess Juliana International Airport on Fri, Jan 31, arriving at O'Hare International Airport. One-way Prices start from $278 including taxes and charges.

      • SXM04:50 pm
        24h 54m
        1 stop
        ORD03:44 pm
        Wed, Jan 29|Sint Maarten - Chicago|Jetblue Airways
        $278
        $278

        Choose Jetblue Airways flights from Sint Maarten to Chicago. The one-way connecting flight with Jetblue Airways departs from Princess Juliana International Airport on Wed, Jan 29, arriving at O'Hare International Airport. One-way Prices start from $278 including taxes and charges.

      • SXM03:30 pm
        28h 8m
        1 stop
        ORD06:38 pm
        Mon, Apr 7|Sint Maarten - Chicago|Delta Air Lines
        $282
        $282

        Choose Delta Air Lines flights from Sint Maarten to Chicago. The one-way connecting flight with Delta Air Lines departs from Princess Juliana International Airport on Mon, Apr 7, arriving at O'Hare International Airport. One-way Prices start from $282 including taxes and charges.

      • SXM05:56 pm
        23h 48m
        1 stop
        ORD03:44 pm
        Sat, Feb 1|Sint Maarten - Chicago|Jetblue Airways
        $287
        $287

        Choose Jetblue Airways flights from Sint Maarten to Chicago. The one-way connecting flight with Jetblue Airways departs from Princess Juliana International Airport on Sat, Feb 1, arriving at O'Hare International Airport. One-way Prices start from $287 including taxes and charges.

      • SXM04:50 pm
        24h 53m
        1 stop
        ORD03:43 pm
        Wed, Feb 5|Sint Maarten - Chicago|Jetblue Airways
        $289
        $289

        Choose Jetblue Airways flights from Sint Maarten to Chicago. The one-way connecting flight with Jetblue Airways departs from Princess Juliana International Airport on Wed, Feb 5, arriving at O'Hare International Airport. One-way Prices start from $289 including taxes and charges.

      • SXM04:25 pm
        27h 34m
        1 stop
        ORD05:59 pm
        Tue, Jan 28|Sint Maarten - Chicago|Jetblue Airways
        $291
        $291

        Choose Jetblue Airways flights from Sint Maarten to Chicago. The one-way connecting flight with Jetblue Airways departs from Princess Juliana International Airport on Tue, Jan 28, arriving at O'Hare International Airport. One-way Prices start from $291 including taxes and charges.

      • SXM02:53 pm
        28h 45m
        1 stop
        ORD05:38 pm
        Wed, Jan 29|Sint Maarten - Chicago|United Airlines
        $294
        $294

        Choose United Airlines flights from Sint Maarten to Chicago. The one-way connecting flight with United Airlines departs from Princess Juliana International Airport on Wed, Jan 29, arriving at O'Hare International Airport. One-way Prices start from $294 including taxes and charges.

      • SXM01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Thu, Jan 23|Sint Maarten - Chicago|United Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Sint Maarten to Chicago?

Explore the best time to buy affordable tickets to Chicago with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Alternative Cheap Routes from Sint Maarten to Chicago

Did you know that you can save money and time on an alternative route from Sint Maarten to Chicago? Check out some of the different available routes below.

  • Cheapest
    Frontier Airlines
    SXM
    06:31 pm
    17h 17m
    2 transfer
    MDW
    09:48 am
    Princess Juliana International Airport - Midway International Airport
    Fri, Feb 21Frontier Airlines
    $192
  • Frontier Airlines
    SXM
    06:29 pm
    21h 26m
    2 transfer
    ORD
    01:55 pm
    Princess Juliana International Airport - O'Hare International Airport
    Sat, Feb 8Frontier Airlines
    $201
  • Frontier Airlines
    SXM
    06:29 pm
    21h 26m
    2 transfer
    ORD
    01:55 pm
    Princess Juliana International Airport - O'Hare International Airport
    Sat, Feb 8Frontier Airlines
    $201
    Find More Flights

Frequently Asked Questions

  • When are flight tickets from Sint Maarten (SXM) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Sint Maarten to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Sint Maarten (SXM) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around $560.

  • How long does it take to fly from Sint Maarten (SXM) to Chicago (CHI) and what is the distance?

    It takes around 5 hours 54 minutes to fly from Sint Maarten (SXM) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Sint Maarten (SXM) to Chicago (CHI)?

    Airlines with flights from Sint Maarten (SXM) to Chicago (CHI): United Airlines.

How to find a cheap flight from Sint Maarten to Chicago

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Sint Maarten to Chicago

Cheapest nonstop flight price$263
Cheapest round-trip ticket price$638
Off-season for travelNovember
Peak season for travelOctober
Flight distance3,524.79 km
Average flight time5 hours 54 minutes
Popular airlineUnited Airlines

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