How long is the flight from St. Maarten to Chicago?

Airlines like Spirit Airlines fly from St. Maarten to Chicago in about 10h 31m. The time it takes to get you to your destination can typically vary by up to . St. Maarten and Chicago are separated by a distance of 2204 mi.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the cheapest flights from St. Maarten to Chicago?

Looking for the cheapest flight from St. Maarten to Chicago? While on average our users pay $578, our data indicates the cheapest price to be $159. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $245.

Can I find deals for flights from St. Maarten to Chicago that include hotel bookings?

Yes. In addition to deals on St. Maarten to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from St. Maarten to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. Maarten to Chicago.

Can I find deals for business class flights from St. Maarten to Chicago?

Yes. Cheapflights offers flight deals from St. Maarten to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$161+ Flights from St. Maarten to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from St. Maarten to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from St. Maarten to Chicago

Cheapest flights from St. Maarten to Chicago
Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

Sun 12/212:20 pmSXM - ORD

Nonstop6h 01mUnited Airlines

Sun 12/288:45 amORD - SXM

Nonstop5h 12mUnited Airlines

Deal found 12/17

$629

Sun 12/213:40 pmSXM - ORD

1 stop21h 38mAir Canada

Sun 12/286:00 pmORD - SXM

2 stops20h 00mAir Canada

Deal found 12/17

$701

Sun 12/213:40 pmSXM - ORD

1 stop21h 38mMultiple Airlines

Sun 12/287:41 pmORD - SXM

1 stop15h 03mMultiple Airlines

Deal found 12/17

$717

Sun 12/211:45 pmSXM - MDW

1 stop10h 37mKLM

Sun 12/2812:45 pmMDW - SXM

1 stop24h 05mKLM

Deal found 12/17

$1,093

Best flights from St. Maarten to Chicago
Discover carefully curated flight deals from St. Maarten to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

Sat 1/173:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$245

Fri 1/164:20 pmSXM - ORD

2 stops27h 32mMultiple Airlines

Fri 1/238:43 pmORD - SXM

1 stop15h 27mMultiple Airlines

Deal found 12/17

$427

Thu 1/223:40 pmSXM - ORD

2 stops29h 15mAir Canada

Sun 1/256:28 pmORD - SXM

1 stop19h 32mAir Canada

Deal found 12/15

$500

Sat 2/143:20 pmSXM - ORD

1 stop10h 27mSpirit Airlines

Sat 2/215:15 amORD - SXM

1 stop7h 00mSpirit Airlines

Deal found 12/16

$256

Sat 1/173:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Sun 1/258:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Deal found 12/17

$256

Fri 1/163:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Sun 1/255:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$256

Fri 1/163:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$281

Sun 1/183:15 pmSXM - ORD

2 stops46h 32mSpirit Airlines

Sun 1/255:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$284

Sun 1/183:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Fri 1/238:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Deal found 12/17

$303

Thu 1/224:20 pmSXM - MDW

2 stops27h 35mWestJet

Mon 1/261:26 pmMDW - SXM

2 stops23h 55mWestJet

Deal found 12/15

$3,170

Last-minute flights from St. Maarten to Chicago
Discover last-minute flight deals from St. Maarten to Chicago. Data last updated December 18, 2025 and is based on user searches.

Sun 12/211:45 pmSXM - MDW

1 stop10h 37mKLM

Sun 12/2812:45 pmMDW - SXM

1 stop24h 05mKLM

Deal found 12/17

$1,093

Thu 12/251:45 pmSXM - MDW

1 stop10h 37mDelta

Sat 1/36:00 amMDW - SXM

1 stop6h 50mDelta

Deal found 12/18

$690

Fri 1/163:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Fri 1/238:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Deal found 12/17

$256

Fri 1/163:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$281

Fri 1/163:15 pmSXM - ORD

1 stop22h 07mMultiple Airlines

Sat 1/244:38 pmORD - SXM

2 stops15h 47mMultiple Airlines

Deal found 12/17

$343

Fri 1/165:00 pmSXM - ORD

2 stops27h 55mAir Canada

Sun 1/251:55 pmORD - SXM

2 stops24h 05mAir Canada

Deal found 12/17

$425

Sat 1/173:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$245

Sat 1/173:15 pmSXM - ORD

2 stops19h 57mSpirit Airlines

Sun 1/255:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$297

Sat 1/175:00 pmSXM - ORD

2 stops20h 06mMultiple Airlines

Sat 1/247:45 amORD - SXM

2 stops30h 36mMultiple Airlines

Deal found 12/17

$418

Sun 1/183:15 pmSXM - ORD

2 stops46h 32mSpirit Airlines

Sun 1/255:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$284

Sun 1/183:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Fri 1/238:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Deal found 12/17

$303

Sun 1/183:15 pmSXM - ORD

2 stops46h 32mSpirit Airlines

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/17

$308

One-way flights from St. Maarten to Chicago
Search for one-way flight options from St. Maarten to Chicago. Find affordable one-way fares based on user searches. Data last updated December 18, 2025.

Thu 1/153:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/16

$161

Sat 1/243:10 pmSXM - ORD

1 stop9h 34mFrontier

Deal found 12/17

$167

Fri 1/163:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Deal found 12/17

$169

Thu 2/123:15 pmSXM - ORD

1 stop10h 09mMultiple Airlines

Deal found 12/16

$170

Mon 1/123:15 pmSXM - ORD

1 stop22h 07mSpirit Airlines

Deal found 12/15

$178

Sat 2/143:20 pmSXM - ORD

1 stop9h 19mFrontier

Deal found 12/15

$184

Tue 2/173:15 pmSXM - ORD

2 stops27h 37mMultiple Airlines

Deal found 12/15

$192

Fri 1/163:15 pmSXM - ORD

2 stops25h 24mMultiple Airlines

Deal found 12/17

$201

Mon 1/123:15 pmSXM - ORD

2 stops22h 53mMultiple Airlines

Deal found 12/16

$202

Sun 1/183:15 pmSXM - ORD

2 stops46h 32mSpirit Airlines

Deal found 12/17

$204

Sun 3/811:30 amSXM - MDW

2 stops27h 11mMultiple Airlines

Deal found 12/16

$332

Fri 3/201:45 pmSXM - MDW

2 stops24h 56mMultiple Airlines

Deal found 12/16

$393

Find flight deals from St. Maarten to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$245 (Super.com)
One-way from	$161 (Cheapflightsfares)
Good one-way deal	$294 or less

Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.

Search Deals

From St. Maarten to Chicago (CHI)

Search Deals

One-way flight from St. Maarten to Chicago (CHI)

Search Deals

Price to beat on a one-way flight from St. Maarten to Chicago (CHI).

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-11:46 pm

1 stop10h 31m

Chicago O'Hare Intl

Sat 1/24

5:15 am-2:10 pm

1 stop6h 55m

$245

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

3:20 pm-11:47 pm

1 stop10h 27m

Chicago O'Hare Intl

Sat 2/21

5:15 am-2:15 pm

1 stop7h 00m

$256

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-11:46 pm

1 stop10h 31m

Chicago O'Hare Intl

Sun 1/25

8:43 pm-2:10 pm

1 stop15h 27m

$256

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 1/16

3:15 pm-11:22 am

1 stop22h 07m

Chicago O'Hare Intl

Sun 1/25

5:15 am-2:10 pm

1 stop6h 55m

$256

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 1/16

3:15 pm-11:22 am

1 stop22h 07m

Chicago O'Hare Intl

Sat 1/24

5:15 am-2:10 pm

1 stop6h 55m

$281

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 1/18

3:15 pm-11:47 am

2 stops46h 32m

Chicago O'Hare Intl

Sun 1/25

5:15 am-2:10 pm

1 stop6h 55m

$284

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 1/18

3:15 pm-11:46 pm

1 stop10h 31m

Chicago O'Hare Intl

Fri 1/23

8:43 pm-2:10 pm

1 stop15h 27m

$303

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 1/16

4:20 pm-5:52 pm

2 stops27h 32m

Chicago O'Hare Intl

Fri 1/23

8:43 pm-2:10 pm

1 stop15h 27m

$427

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 1/22

3:40 pm-6:55 pm

2 stops29h 15m

Chicago O'Hare Intl

Sun 1/25

6:28 pm-4:00 pm

1 stop19h 32m

$500

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 1/22

4:20 pm-5:55 pm

2 stops27h 35m

Chicago Midway

Mon 1/26

1:26 pm-3:21 pm

2 stops23h 55m

$3,170

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 25 results

Best time to book a flight from St. Maarten to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Maarten with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from St. Maarten to Chicago

What is the cheapest time of day to fly from SX to CHI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from St. Maarten to Chicago as you normally would.

Related info for your journey

How long is the flight from St. Maarten to Chicago?
Airlines like Spirit Airlines fly from St. Maarten to Chicago in about 10h 31m. The time it takes to get you to your destination can typically vary by up to . St. Maarten and Chicago are separated by a distance of 2204 mi.
What are the cheapest flights from St. Maarten to Chicago?
Looking for the cheapest flight from St. Maarten to Chicago? While on average our users pay $578, our data indicates the cheapest price to be $159. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $245.
Can I find deals for flights from St. Maarten to Chicago that include hotel bookings?
Yes. In addition to deals on St. Maarten to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from St. Maarten to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. Maarten to Chicago.
Can I find deals for business class flights from St. Maarten to Chicago?
Yes. Cheapflights offers flight deals from St. Maarten to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Lansing

Merrillville

Hammond

Porter

Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$161+ Cheap flights from St. Maarten to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from St. Maarten to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from St. Maarten to Chicago

Cheapest flights from St. Maarten to ChicagoExplore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

Find flight deals from St. Maarten to Chicago

Keep the following information in mind while searching for St. Maarten to Chicago flight deals. Data was last updated December 18, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Good one-way deal

Cheapflights Fare Finder

Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

Best time to book a flight from St. Maarten to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Maarten with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from St. Maarten to Chicago

What is the cheapest time of day to fly from SX to CHI?

Find hourly flight availability from St. Maarten to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Related info for your journey

Find useful and relevant information for your journey from St. Maarten to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

How long is the flight from St. Maarten to Chicago?

What are the cheapest flights from St. Maarten to Chicago?

Can I find deals for flights from St. Maarten to Chicago that include hotel bookings?

How can I find direct flights from St. Maarten to Chicago?

Can I find deals for business class flights from St. Maarten to Chicago?

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for St. Maarten to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from St. Maarten to Chicago
Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.