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Flights from Sint Maarten to Chicago
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Flights from Sint Maarten to Chicago Starting at £215

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
        SXM13:16
        5h 54m
        Nonstop
        ORD18:10
        Sun, Mar 9|Sint Maarten - Chicago|United Airlines
        £331£464
        28% OFF
        28% OFF
        £464£331

        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 £331 including taxes and charges.

      • SXM14:46
        5h 54m
        Nonstop
        ORD18:40
        Sun, Mar 2|Sint Maarten - Chicago|United Airlines
        £348£464
        25% OFF
        25% OFF
        £464£348

        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 £348 including taxes and charges.

      • SXM14:53
        18h 56m
        1 stop
        ORD07:49
        Thu, Jan 16|Sint Maarten - Chicago|United Airlines
        £215£464
        54% OFF
        54% OFF
        £464£215

        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 £215 including taxes and charges.

      • SXM16:50
        19h 5m
        1 stop
        ORD09:55
        Fri, Jan 31|Sint Maarten - Chicago|Jetblue Airways
        £227
        £227

        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 £227 including taxes and charges.

      • SXM16:50
        24h 54m
        1 stop
        ORD15:44
        Wed, Jan 29|Sint Maarten - Chicago|Jetblue Airways
        £228
        £228

        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 £228 including taxes and charges.

      • SXM15:30
        28h 8m
        1 stop
        ORD18:38
        Mon, Apr 7|Sint Maarten - Chicago|Delta Air Lines
        £231
        £231

        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 £231 including taxes and charges.

      • SXM17:56
        23h 48m
        1 stop
        ORD15:44
        Sat, Feb 1|Sint Maarten - Chicago|Jetblue Airways
        £235
        £235

        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 £235 including taxes and charges.

      • SXM16:50
        24h 53m
        1 stop
        ORD15:43
        Wed, Feb 5|Sint Maarten - Chicago|Jetblue Airways
        £236
        £236

        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 £236 including taxes and charges.

      • SXM16:25
        27h 34m
        1 stop
        ORD17:59
        Tue, Jan 28|Sint Maarten - Chicago|Jetblue Airways
        £238
        £238

        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 £238 including taxes and charges.

      • SXM14:53
        28h 45m
        1 stop
        ORD17:38
        Wed, Jan 29|Sint Maarten - Chicago|United Airlines
        £240
        £240

        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 £240 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.

Find the best time to fly from Sint Maarten to Chicago

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Sint Maarten have changed and are set to move below.

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

Alternative Routes from Sint Maarten to Chicago

There are various non-direct routes from Sint Maarten to Chicago which could be cheaper and faster! Check out these alternative options to see if they could work for your trip.

  • Cheapest
    Frontier Airlines
    SXM
    18:31
    17h 17m
    2 transfer
    MDW
    09:48
    Princess Juliana International Airport - Midway International Airport
    Fri, Feb 21Frontier Airlines
    £157
  • Frontier Airlines
    SXM
    18:29
    21h 26m
    2 transfer
    ORD
    13:55
    Princess Juliana International Airport - O'Hare International Airport
    Sat, Feb 8Frontier Airlines
    £165
  • Frontier Airlines
    SXM
    18:29
    21h 26m
    2 transfer
    ORD
    13:55
    Princess Juliana International Airport - O'Hare International Airport
    Sat, Feb 8Frontier Airlines
    £165
    Find More Flights

FAQ

  • 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 date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

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

    According to Trip.com's data, the lowest price is around £458.

  • How long is the flight from Sint Maarten (SXM) to Chicago (CHI)?

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

  • 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.

  • What's the most popular airline for direct flights from Sint Maarten (SXM) to Chicago (CHI)?

    United Airlines operates 1 direct flights from Sint Maarten (SXM) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Sint Maarten to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
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 Information from Sint Maarten to Chicago

Cheapest direct flight price£215
Cheapest return ticket price£522
Off-season travel monthNovember
Peak season for travelOctober
Flight distance3,524.79km
Average flight time5 hours 54 minutes
Popular airlineUnited Airlines

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