HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$178+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Keep the following information in mind while searching for St. Maarten to Chicago flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$362
(Booking.com)

One-way from

$178
(Kiwi.com)

Popular in

April

Cheapest in

February

Average price

$338

Good one-way deal

$459 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
Highest demand for flights based on searches. 4% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
Price to beat on a one-way flight from St. Maarten to Chicago (CHI).
Search Deals

Find 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 February 20, 2025.

This Booking.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/302:34 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Fri 5/95:05 amORD - SXM
1 stop7h 56mSpirit Airlines
Deal found 2/18$362
This Kiwi.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/302:34 pmSXM - ORD
1 stop11h 07mMultiple Airlines
Fri 5/94:15 pmORD - SXM
2 stops18h 05mMultiple Airlines
Deal found 2/18$421
This eDestinos deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1212:18 pmSXM - ORD
2 stops24h 14mFrontier
Fri 8/16:00 amORD - SXM
2 stops27h 58mFrontier
Deal found 2/19$555
This American Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/292:14 pmSXM - ORD
2 stops10h 35mAmerican Airlines
Fri 5/95:00 amORD - SXM
2 stops9h 31mAmerican Airlines
Deal found 2/18$662
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/303:55 pmSXM - MDW
2 stops25h 45mMultiple Airlines
Mon 4/75:35 pmMDW - SXM
1 stop19h 41mMultiple Airlines
Deal found 2/20$781
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/191:25 pmSXM - ORD
Nonstop5h 43mUnited Airlines
Fri 4/254:15 pmORD - SXM
1 stop19h 14mUnited Airlines
Deal found 2/20$806
This Flysmarter deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/91:16 pmSXM - ORD
Nonstop5h 54mLufthansa
Sun 3/167:40 pmORD - SXM
1 stop16h 11mLufthansa
Deal found 2/20$861
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/91:40 pmSXM - MDW
1 stop9h 43mDelta
Sun 3/164:59 pmMDW - SXM
1 stop20h 02mDelta
Deal found 2/20$1,016
This WestJet deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/112:10 pmSXM - ORD
2 stops27h 34mWestJet
Sat 5/175:30 pmORD - SXM
2 stops18h 45mWestJet
Deal found 2/20$1,138
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/303:10 pmSXM - MDW
2 stops28h 08mWestJet
Mon 4/71:15 pmMDW - SXM
2 stops24h 01mWestJet
Deal found 2/20$1,202
This Gotogate deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/93:55 pmSXM - ORD
2 stops28h 43mAir Canada
Sun 3/169:40 pmORD - SXM
2 stops16h 35mAir Canada
Deal found 2/20$1,754

Find flights from St. Maarten to Chicago within your budget

Customize your flight search to find flights from St. Maarten to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

St. Maarten

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/30

2:34 pm-12:41 am

1 stop11h 07m

Chicago O'Hare Intl

Fri 5/9

5:05 am-2:01 pm

1 stop7h 56m

$362

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 4/30

2:34 pm-12:41 am

1 stop11h 07m

Chicago O'Hare Intl

Fri 5/9

4:15 pm-11:20 am

2 stops18h 05m

$421

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 7/12

12:18 pm-11:32 am

2 stops24h 14m

Chicago O'Hare Intl

Fri 8/1

6:00 am-10:58 am

2 stops27h 58m

$555

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 4/29

2:14 pm-11:49 pm

2 stops10h 35m

Chicago O'Hare Intl

Fri 5/9

5:00 am-3:31 pm

2 stops9h 31m

$662

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 3/30

3:55 pm-4:40 pm

2 stops25h 45m

Chicago Midway

Mon 4/7

5:35 pm-2:16 pm

1 stop19h 41m

$781

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/19

1:25 pm-6:08 pm

Nonstop5h 43m

Chicago O'Hare Intl

Fri 4/25

4:15 pm-12:29 pm

1 stop19h 14m

$806

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 3/9

1:16 pm-6:10 pm

Nonstop5h 54m

Chicago O'Hare Intl

Sun 3/16

7:40 pm-12:51 pm

1 stop16h 11m

$861

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 3/9

1:40 pm-10:23 pm

1 stop9h 43m

Chicago Midway

Sun 3/16

4:59 pm-2:01 pm

1 stop20h 02m

$1,016

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 5/11

2:10 pm-4:44 pm

2 stops27h 34m

Chicago O'Hare Intl

Sat 5/17

5:30 pm-1:15 pm

2 stops18h 45m

$1,138

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 3/30

3:10 pm-6:18 pm

2 stops28h 08m

Chicago Midway

Mon 4/7

1:15 pm-2:16 pm

2 stops24h 01m

$1,202

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 20 results
1
2

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.

Travel insights for flights from St. Maarten to Chicago

Get recent, data-driven insights about flights from St. Maarten to Chicago including ideal travel times, pricing trends, and more.

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 February 20, 2025.

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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 20, 2025.
To help decide which airline to fly from St. Maarten to Chicago, see what other customers have to say about Delta, United Airlines and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.2
Good
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Canada
7.0
Good
8,748 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines to fly from St. Maarten to Chicago one-way?

    $239 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Air Canada and American Airlines, with prices starting from $375 and $390, respectively.

  • 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 $809, our data indicates the cheapest price to be $446. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $362.

  • 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.

  • What is the cheapest month to book a flight from St. Maarten to Chicago?

    Currently, August is the cheapest month in which you can book a flight from St. Maarten to Chicago (average of $245). Flying from St. Maarten to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near St. Maarten?

Book flights to St. Maarten if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Nassau to Midway flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
George Town to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to O'Hare Intl flights
Kingston to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
Nassau to St. Louis flights
Saint Thomas Island to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Simpson Bay to Midway flights
Christiansted to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Port Au Prince to Midway flights
St. John's to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Vieques to O'Hare Intl flights
Oranjestad to St. Louis flights
St. George's to St. Louis flights
Culebra to O'Hare Intl flights
Aguadilla to Midway flights

Top airline flying from St. Maarten to Chicago

Discover the top airline that operate flights from St. Maarten to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%
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.