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$323+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$623
(American Airlines)

One-way from

$323

Good one-way deal

$574 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
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From St. Maarten to Chicago (CHI)
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One-way flight from St. Maarten to Chicago (CHI)
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Price to beat on a one-way flight from St. Maarten to Chicago (CHI).
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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 April 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 10/92:40 pmSXM - ORD
1 stop8h 54mAmerican Airlines
Wed 10/156:57 amORD - SXM
1 stop7h 13mAmerican Airlines
Deal found 4/28$623
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Thu 6/122:10 pmSXM - ORD
1 stop26h 40mMultiple Airlines
Thu 6/1910:31 amORD - SXM
3 stops26h 29mMultiple Airlines
Deal found 4/28$716
This WestJet deal was found by Cheapflights users on 4/28. 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.
Thu 10/92:10 pmSXM - ORD
2 stops27h 33mWestJet
Wed 10/157:00 amORD - SXM
2 stops29h 19mWestJet
Deal found 4/28$1,256
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Thu 10/911:55 amSXM - ORD
3 stops31h 55mUnited Airlines
Wed 10/152:20 pmORD - SXM
2 stops20h 00mUnited Airlines
Deal found 4/28$8,197

Cheapflights Fare Finder

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 April 29, 2025.
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

Fly from

St. Maarten

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

2:40 pm-10:34 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 10/15

6:57 am-3:10 pm

1 stop7h 13m

$623

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 6/12

2:10 pm-3:50 pm

1 stop26h 40m

Chicago O'Hare Intl

Thu 6/19

10:31 am-2:00 pm

3 stops26h 29m

$716

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

2:10 pm-4:43 pm

2 stops27h 33m

Chicago O'Hare Intl

Wed 10/15

7:00 am-1:19 pm

2 stops29h 19m

$1,256

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

11:55 am-6:50 pm

3 stops31h 55m

Chicago O'Hare Intl

Wed 10/15

2:20 pm-11:20 am

2 stops20h 00m

$8,197

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 6/21

12:36 pm-8:17 pm

1 stop8h 41m

$323

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/21

3:03 pm-11:25 pm

1 stop9h 22m

$466

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 6/22

3:55 pm-11:30 pm

1 stop8h 35m

$695

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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?

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 April 29, 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 April 29, 2025.
United Airlines
7.4
Good
8,696 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
United Airlines
7.4
Good
8,696 reviews
United Airlines
7.4
Good
8,696 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
JetBlue
7.3
Good
2,922 reviews
United Airlines
7.4
Good
8,696 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,696 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
WestJet
7.2
Good
2,823 reviews
United Airlines
7.4
Good
8,696 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
Frontier
6.0
Okay
3,284 reviews
United Airlines
7.4
Good
8,696 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

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?

    $323 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and United Airlines, with prices starting from $466 and $695, 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 $605, our data indicates the cheapest price to be $538. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $348.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for St. Maarten to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%

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