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$265+ Cheap flights from Saint Martin Island 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Saint Martin Island to Chicago

Keep the following information in mind while searching for Saint Martin Island to Chicago flight deals. Data was last updated May 1, 2025.

Round-trip from

$345
(Flightnetwork)

One-way from

$265
(Cheapflightsfares)
From Saint Martin Island to Chicago (CHI)
Search Deals
One-way flight from Saint Martin Island to Chicago (CHI)
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Find flight deals from Saint Martin Island to Chicago

Cheapest flights from Saint Martin Island to Chicago
Explore the most affordable flight options available from Saint Martin Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Flightnetwork deal was found by Cheapflights users on 4/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/303:05 pmSXM - ORD
1 stop10h 00mMultiple Airlines
Fri 6/65:08 pmORD - SXM
1 stop17h 15mMultiple Airlines
Deal found 4/29$345
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Fri 5/303:05 pmSXM - ORD
1 stop10h 00mSpirit Airlines
Fri 6/64:35 pmORD - SXM
2 stops20h 25mSpirit Airlines
Deal found 4/29$417
This American Airlines deal was found by Cheapflights users on 4/30. 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 10/156:00 amORD - SXM
1 stop8h 10mAmerican Airlines
Deal found 4/30$623
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/213:55 pmSXM - ORD
1 stop17h 07mUnited Airlines
Sat 5/245:53 pmORD - SXM
1 stop17h 36mUnited Airlines
Deal found 4/30$812
This WestJet deal was found by Cheapflights users on 4/30. 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 10/1510:05 amORD - SXM
2 stops26h 14mWestJet
Deal found 4/30$1,358

Cheapflights Fare Finder

Customize your flight search to find flights from Saint Martin Island 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 May 1, 2025.
Use the filters below to find and compare flights from Saint Martin Island to Chicago that are best for you.

Fly from

Saint Martin Island

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 5/30

3:05 pm-12:05 am

1 stop10h 00m

Chicago O'Hare Intl

Fri 6/6

5:08 pm-11:23 am

1 stop17h 15m

$345

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 5/30

3:05 pm-12:05 am

1 stop10h 00m

Chicago O'Hare Intl

Fri 6/6

4:35 pm-2:00 pm

2 stops20h 25m

$417

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

6:00 am-3:10 pm

1 stop8h 10m

$623

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 5/21

3:55 pm-8:02 am

1 stop17h 07m

Chicago O'Hare Intl

Sat 5/24

5:53 pm-12:29 pm

1 stop17h 36m

$812

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

10:05 am-1:19 pm

2 stops26h 14m

$1,358

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 8/8

2:56 pm-8:51 am

1 stop18h 55m

$265

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 8/8

2:56 pm-8:07 am

2 stops18h 11m

$384

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Best time to book a flight from Saint Martin Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Saint Martin Island 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 Saint Martin Island to Chicago

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

Find hourly flight availability from Saint Martin Island 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 May 1, 2025.

When flying from Saint Martin Island to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 May 1, 2025.
United Airlines
7.4
Good
8,696 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

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

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

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

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

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
2,826 reviews
United Airlines
7.4
Good
8,696 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

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.
Spirit Airlines
6.3
Okay
7,963 reviews
United Airlines
7.4
Good
8,696 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

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 Saint Martin Island 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 flights from Saint Martin Island to Chicago?

    The cheapest flight price from Saint Martin Island to Chicago is $538. On average you can expect to pay $605. The most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), can usually be booked for $345.

  • Can I find deals for flights from Saint Martin Island to Chicago that include hotel bookings?

    Yes. In addition to deals on Saint Martin Island to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Saint Martin Island to Chicago?

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

  • Can I find deals for business class flights from Saint Martin Island to Chicago?

    Yes. Cheapflights offers flight deals from Saint Martin Island 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 Saint Martin Island to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Saint Martin Island to Chicago (average of $245). Flying from Saint Martin Island 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 Saint Martin Island?

Book flights to Saint Martin Island if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Saint Martin Island 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 Saint Martin Island to Chicago

Discover the top airline that operate flights from Saint Martin Island 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%

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