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Cheap Flights from Sint Maarten to Chicago
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Cheap Flights from Sint Maarten to Chicago starting at S$ 358

Discover our range of affordable one-way and round-trip flights from Sint Maarten to Chicago and kick-start your next adventure today!

  • One way
  • Round-trip
      • Cheapest nonstop
        SXM14:46
        5h 54m
        Nonstop
        ORD18:40
        Sun, Dec 22|Sint Maarten - Chicago|United Airlines
        S$ 525S$ 601
        13% OFF
        13% OFF
        S$ 601S$ 525

        Fly from Sint Maarten to Chicago on Sun, Dec 22 with United Airlines. One-way direct flights with United Airlines depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 525 including taxes and charges.

      • SXM14:46
        5h 54m
        Nonstop
        ORD18:40
        Sun, Dec 29|Sint Maarten - Chicago|United Airlines
        S$ 541S$ 601
        10% OFF
        10% OFF
        S$ 601S$ 541

        Fly from Sint Maarten to Chicago on Sun, Dec 29 with United Airlines. One-way direct flights with United Airlines depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 541 including taxes and charges.

      • SXM14:53
        18h 56m
        1 stop
        ORD07:49
        Thu, Jan 16|Sint Maarten - Chicago|United Airlines
        S$ 358S$ 601
        40% OFF
        40% OFF
        S$ 601S$ 358

        Fly from Sint Maarten to Chicago on Thu, Jan 16 with United Airlines. One-way connecting flights with United Airlines depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 358 including taxes and charges.

      • SXM16:24
        17h 26m
        1 stop
        ORD07:50
        Thu, Jan 9|Sint Maarten - Chicago|Jetblue Airways
        S$ 373
        S$ 373

        Fly from Sint Maarten to Chicago on Thu, Jan 9 with Jetblue Airways. One-way connecting flights with Jetblue Airways depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 373 including taxes and charges.

      • SXM16:10
        20h 10m
        1 stop
        MDW10:20
        Tue, Dec 24|Sint Maarten - Chicago|Westjet
        S$ 376
        S$ 376

        Fly from Sint Maarten to Chicago on Tue, Dec 24 with Westjet. One-way connecting flights with Westjet depart Princess Juliana International Airport and arrive Midway International Airport starting at S$ 376 including taxes and charges.

      • SXM16:50
        24h 54m
        1 stop
        ORD15:44
        Wed, Jan 29|Sint Maarten - Chicago|Jetblue Airways
        S$ 379
        S$ 379

        Fly from Sint Maarten to Chicago on Wed, Jan 29 with Jetblue Airways. One-way connecting flights with Jetblue Airways depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 379 including taxes and charges.

      • SXM18:25
        14h 40m
        1 stop
        ORD07:05
        Sat, Jan 11|Sint Maarten - Chicago|Sun Country Airlines
        S$ 402
        S$ 402

        Fly from Sint Maarten to Chicago on Sat, Jan 11 with Sun Country Airlines. One-way connecting flights with Sun Country Airlines depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 402 including taxes and charges.

      • SXM16:50
        24h 54m
        1 stop
        ORD15:44
        Wed, Jan 15|Sint Maarten - Chicago|Jetblue Airways
        S$ 403
        S$ 403

        Fly from Sint Maarten to Chicago on Wed, Jan 15 with Jetblue Airways. One-way connecting flights with Jetblue Airways depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 403 including taxes and charges.

      • SXM14:53
        10h 7m
        1 stop
        ORD23:00
        Wed, Dec 18|Sint Maarten - Chicago|United Airlines
        S$ 421
        S$ 421

        Fly from Sint Maarten to Chicago on Wed, Dec 18 with United Airlines. One-way connecting flights with United Airlines depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 421 including taxes and charges.

      • SXM14:53
        19h 49m
        1 stop
        ORD08:42
        Wed, Feb 5|Sint Maarten - Chicago|United Airlines
        S$ 427
        S$ 427

        Fly from Sint Maarten to Chicago on Wed, Feb 5 with United Airlines. One-way connecting flights with United Airlines depart Princess Juliana International Airport and arrive O'Hare International Airport starting at S$ 427 including taxes and charges.

      • SXM01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Mon, Dec 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.

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 lowest average weekly prices of the corresponding route on Trip.com.

Cheapest Airlines flying from Sint Maarten to Chicago

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from Sint Maarten to Chicago.

Frontier Airlines
From S$ 282
Silver Airways
From S$ 332
United Airlines
From S$ 357
Jetblue Airways
From S$ 373
Westjet
From S$ 376
Sun Country Airlines
From S$ 402
Air Canada
From S$ 441
Copa Airlines
From S$ 482
Caribbean Airlines
From S$ 485
Delta Air Lines
From S$ 504

Find more flights and airlines

Alternative Routes from Sint Maarten to Chicago

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Chicago from Sint Maarten which could help you save money and time.

  • Cheapest
    Frontier Airlines
    SXM
    18:29
    22h 52m
    2 transfer
    MDW
    15:21
    Princess Juliana International Airport - Midway International Airport
    Sat, Feb 8Frontier Airlines
    S$ 282
  • Frontier Airlines
    SXM
    18:29
    21h 26m
    2 transfer
    ORD
    13:55
    Princess Juliana International Airport - O'Hare International Airport
    Sat, Feb 8Frontier Airlines
    S$ 283
  • Frontier Airlines
    SXM
    18:29
    21h 26m
    2 transfer
    ORD
    13:55
    Princess Juliana International Airport - O'Hare International Airport
    Sat, Feb 8Frontier Airlines
    S$ 283
    Find More Flights

Frequently Asked Questions

  • When to buy 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 is a flight from Sint Maarten (SXM) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 762.

  • How long is a 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?

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

Find cheapest flight ticket from Sint Maarten to Chicago

Cheapest direct flight priceS$ 358
Cheapest return ticket priceS$ 853
Off-season for travelNovember
Peak season for travelSeptember
Flight distance3,524.79km
Average flight time5 hours 54 minutes
Popular airlineUnited Airlines

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