Rome2Rio

How to get fromChicago to Sint Maartenby plane or train

Find Transport to Sint Maarten

See all options
QR code to download the Rome2Rio app

Download the Rome2Rio travel app

Scan QR code with your phone to download the app

Download on the App StoreGet it on Google Play

There are 3 ways to get from Chicago to Sint Maarten by plane or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly from Chicago Midway International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Princess Juliana International Airport (SXM)plane plane MDW - SXM
    9h 49m
    $272–1,025
  2. Fly from Chicago O'Hare International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM)plane plane ORD - SXM
    8h 7m
    $182–625
  3. Train to General Mitchell International Airport, fly

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Princess Juliana International Airport (SXM)plane plane MKE - SXM
    11h 13m
    $329–1,156

Chicago Midway International Airport (MDW) to Princess Juliana International Airport (SXM) flights

Calendar15Weekly Planes
Duration7h 11mAverage Duration
Ticket$229Cheapest Price
See schedules

Comparing Your Travel Options

What companies run services between Chicago, IL, USA and Sint Maarten?

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Princess Juliana International Airport (SXM) twice daily.

Airlines
Train operators

Want to know more about travelling around Sint Maarten

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides