$265 Cheap Flights from Sint Maarten to Chicago (SXM to CHI)

App

Customer Support

USD

Find Bookings

Trip.com

Flights

Flights to United States

Flights to Illinois

Flights to Chicago

Flights from Sint Maarten to Chicago

Worldwide Coverage

Flights to over 5,000 cities

One-stop Service Guarantee

Price guaranteed upon confirmed payment, booking guaranteed once tickets issued

Secure Payment

Convenient & reliable booking and payment system

Cheap flight deals from Sint Maarten to Chicago Starting at $265

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

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.

Find cheap airlines flights from Sint Maarten to Chicago

Which airline provides the cheapest flights from Sint Maarten to Chicago? Discover the option that best suits your travel needs before embarking on your journey.

Frontier Airlines

From $209

Silver Airways

From $246

United Airlines

From $265

Jetblue Airways

From $277

WestJet

From $279

Sun Country Airlines

From $298

Air Canada

From $327

Copa Airlines

From $357

Caribbean Airlines

From $359

Delta Air Lines

From $373

Find more flights and airlines

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
SXM
18:29
22h 52m
2 transfer
MDW
15:21
Princess Juliana International Airport - Midway International Airport
Sat, Feb 8Frontier Airlines
$209
SXM
18:29
21h 26m
2 transfer
ORD
13:55
Princess Juliana International Airport - O'Hare International Airport
Sat, Feb 8Frontier Airlines
$210
SXM
18:29
21h 26m
2 transfer
ORD
13:55
Princess Juliana International Airport - O'Hare International Airport
Sat, Feb 8Frontier Airlines
$210
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 $565.
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.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

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	$265
Cheapest round-trip ticket price	$632
Off-season for travel	November
Peak season for travel	September
Flight distance	3,524.79 km
Average flight time	5 hours 54 minutes
Popular airline	United Airlines