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

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $139. Delta flights start at $308 while deals on American Airlines start at $378 one-way.

What is the cheapest day to fly from Chicago to St. Maarten?

Travelers seeking maximum savings on their Chicago to St. Maarten flight should consider departing on Sunday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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

Looking at all options, your cheapest flight can be booked for $757. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $337 on average our data indicates $1,043 when flying from Chicago to St. Maarten.

What are the most popular airlines that fly from Chicago to St. Maarten?

Consider American Airlines, Delta or Spirit Airlines when booking your flight. These represent the most popular airlines when flying from Chicago to St. Maarten.

What is the cheapest day to fly round-trip from Chicago to St. Maarten?

Friday flights are found to be more expensive to fly from Chicago to St. Maarten. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to St. Maarten.

How far in advance should I book a flight from Chicago to St. Maarten?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 51 days in advance, which can save you up to 78% on flights from Chicago to St. Maarten compared to booking the week you need them. Waiting 51 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $442. For sooner than that we have options available in the next 3 days from $1,114.

What is the cheapest month to fly from Chicago to St. Maarten?

September can be a great time to fly to St. Maarten from Chicago with a flight ticket averaging about $733. Cheapflights users have found deals in the month of September for as cheap as $369. The most expensive prices can be found in the month of March.

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

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

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

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

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

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

$659+ Flights from Chicago to St. Maarten

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Cheap flight deals from Chicago to St. Maarten

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$377 (Cheapflightsfares)
One-way from	$139 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$727
Good round-trip deal	$795 or less

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

Search Deals

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

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From Chicago (CHI) to St. Maarten

Search Deals

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

Search Deals

Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.

Search Deals

Find flight deals from Chicago to St. Maarten

Cheapest flights from Chicago to St. Maarten
Explore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2025.

Fri 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

Sat 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

Sat 5/175:05 amORD - SXM

1 stop7h 55mMultiple Airlines

Sat 5/2412:34 pmSXM - ORD

1 stop20h 48mMultiple Airlines

Deal found 4/1

$403

Fri 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

Sat 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/1

$431

Thu 7/35:10 amORD - SXM

2 stops53h 18mFrontier

Mon 7/76:26 pmSXM - ORD

2 stops30h 02mFrontier

Deal found 4/1

$499

Fri 4/118:25 pmORD - SXM

1 stop18h 20mAir Canada

Mon 4/144:15 pmSXM - ORD

1 stop17h 40mAir Canada

Deal found 4/1

$571

Tue 5/135:30 amORD - SXM

1 stop7h 24mDelta

Tue 5/203:19 pmSXM - ORD

1 stop9h 39mDelta

Deal found 4/1

$622

Sat 5/37:17 pmORD - SXM

1 stop16h 57mAmerican Airlines

Wed 5/73:24 pmSXM - ORD

2 stops16h 02mAmerican Airlines

Deal found 4/1

$627

Tue 7/81:07 amORD - SXM

1 stop9h 17mCopa Airlines

Sun 7/1312:23 pmSXM - ORD

1 stop12h 57mCopa Airlines

Deal found 4/1

$783

Sat 4/266:04 amMDW - SXM

1 stop7h 01mDelta

Sat 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/1

$792

Wed 5/216:00 amORD - SXM

1 stop7h 43mUnited Airlines

Fri 5/301:35 pmSXM - ORD

1 stop9h 37mUnited Airlines

Deal found 4/1

$805

Fri 5/169:42 amMDW - SXM

3 stops27h 18mMultiple Airlines

Fri 5/233:05 pmSXM - MDW

3 stops27h 09mMultiple Airlines

Deal found 4/1

$814

Wed 6/181:40 pmORD - SXM

2 stops22h 35mWestJet

Sun 6/222:10 pmSXM - ORD

2 stops51h 34mWestJet

Deal found 4/1

$827

Best flights from Chicago to St. Maarten
Discover carefully curated flight deals from Chicago to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 2, 2025.

Fri 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

Sat 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

Sat 5/175:05 amORD - SXM

1 stop7h 55mMultiple Airlines

Sat 5/2412:34 pmSXM - ORD

1 stop20h 48mMultiple Airlines

Deal found 4/1

$403

Fri 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

Sat 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/1

$431

Fri 4/118:25 pmORD - SXM

1 stop18h 20mAir Canada

Mon 4/144:15 pmSXM - ORD

1 stop17h 40mAir Canada

Deal found 4/1

$571

Tue 5/135:30 amORD - SXM

1 stop7h 24mDelta

Thu 5/223:19 pmSXM - ORD

1 stop9h 39mDelta

Deal found 4/1

$622

Sat 5/37:17 pmORD - SXM

1 stop16h 57mAmerican Airlines

Wed 5/73:24 pmSXM - ORD

2 stops16h 02mAmerican Airlines

Deal found 4/1

$627

Tue 7/81:07 amORD - SXM

1 stop9h 17mCopa Airlines

Sun 7/1312:23 pmSXM - ORD

1 stop12h 57mCopa Airlines

Deal found 4/1

$783

Wed 5/216:00 amORD - SXM

1 stop7h 43mUnited Airlines

Fri 5/301:35 pmSXM - ORD

1 stop9h 37mUnited Airlines

Deal found 4/1

$805

Sat 6/141:40 pmORD - SXM

2 stops22h 35mWestJet

Sun 6/222:10 pmSXM - ORD

2 stops51h 34mWestJet

Deal found 4/1

$848

Thu 7/35:10 amORD - SXM

2 stops53h 18mFrontier

Mon 7/76:26 pmSXM - ORD

2 stops30h 02mFrontier

Deal found 4/1

$499

Sat 4/266:04 amMDW - SXM

1 stop7h 01mDelta

Sat 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/1

$792

Fri 5/169:42 amMDW - SXM

3 stops27h 18mMultiple Airlines

Fri 5/233:05 pmSXM - MDW

3 stops27h 09mMultiple Airlines

Deal found 4/1

$814

Last-minute flights from Chicago to St. Maarten
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated April 2, 2025 and is based on user searches.

Wed 4/95:00 amORD - SXM

1 stop7h 14mAmerican Airlines

Tue 4/153:18 pmSXM - ORD

1 stop9h 36mAmerican Airlines

Deal found 4/1

$842

Wed 4/96:00 amORD - SXM

1 stop7h 43mUnited Airlines

Tue 4/151:35 pmSXM - ORD

1 stop11h 05mUnited Airlines

Deal found 4/1

$932

Wed 4/912:48 pmMDW - SXM

2 stops48h 28mWestJet

Tue 4/153:10 pmSXM - MDW

2 stops42h 57mWestJet

Deal found 4/1

$3,428

Thu 4/107:33 pmORD - SXM

1 stop17h 27mSpirit Airlines

Wed 4/163:05 pmSXM - ORD

1 stop10h 15mSpirit Airlines

Deal found 4/1

$496

Thu 4/106:15 amORD - SXM

2 stops31h 01mWestJet

Tue 4/153:10 pmSXM - ORD

2 stops49h 46mWestJet

Deal found 4/1

$2,383

Fri 4/117:05 pmORD - SXM

1 stop20h 18mMultiple Airlines

Wed 4/163:05 pmSXM - ORD

1 stop10h 15mMultiple Airlines

Deal found 4/1

$410

Fri 4/118:25 pmORD - SXM

1 stop18h 20mAir Canada

Mon 4/144:15 pmSXM - ORD

1 stop17h 40mAir Canada

Deal found 4/1

$571

Fri 4/116:00 amMDW - SXM

1 stop6h 59mDelta

Tue 4/151:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/1

$907

Sat 4/125:45 amORD - SXM

1 stop7h 14mDelta

Wed 4/161:46 pmSXM - ORD

1 stop8h 04mDelta

Deal found 4/1

$907

Fri 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

Sat 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

Sat 4/266:04 amMDW - SXM

1 stop7h 01mDelta

Sat 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/1

$792

Sat 5/37:17 pmORD - SXM

1 stop16h 57mAmerican Airlines

Wed 5/73:24 pmSXM - ORD

2 stops16h 02mAmerican Airlines

Deal found 4/1

$627

One-way flights from Chicago to St. Maarten
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated April 2, 2025.

Fri 4/255:36 amORD - SXM

1 stop7h 24mSpirit Airlines

Deal found 3/31

$139

Sat 4/1911:45 amORD - SXM

2 stops22h 35mMultiple Airlines

Deal found 3/31

$233

Sun 4/1310:19 amMDW - SXM

2 stops26h 41mMultiple Airlines

Deal found 4/1

$260

Mon 5/125:30 amORD - SXM

1 stop7h 24mDelta

Deal found 4/1

$308

Fri 5/165:00 amORD - SXM

1 stop7h 15mAmerican Airlines

Deal found 4/1

$378

Sun 4/136:00 amMDW - SXM

1 stop6h 59mDelta

Deal found 4/1

$443

Sat 4/1210:37 amORD - SXM

Nonstop5h 12mUnited Airlines

Deal found 4/1

$463

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/18

7:47 pm-2:00 pm

1 stop17h 13m

Simpson Bay Princess Juliana

Sat 5/3

3:05 pm-12:58 am

1 stop10h 53m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/17

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 5/24

12:34 pm-8:22 am

1 stop20h 48m

$403

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$431

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 7/3

5:10 am-11:28 am

2 stops53h 18m

Simpson Bay Princess Juliana

Mon 7/7

6:26 pm-11:28 pm

2 stops30h 02m

$499

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 5/13

5:30 am-1:54 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Tue 5/20

3:19 pm-11:58 pm

1 stop9h 39m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/3

7:17 pm-1:14 pm

1 stop16h 57m

Simpson Bay Princess Juliana

Wed 5/7

3:24 pm-6:26 am

2 stops16h 02m

$627

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 7/8

1:07 am-11:24 am

1 stop9h 17m

Simpson Bay Princess Juliana

Sun 7/13

12:23 pm-12:20 am

1 stop12h 57m

$783

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/26

6:04 am-2:05 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Sat 5/3

1:46 pm-10:22 pm

1 stop9h 36m

$792

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 5/21

6:00 am-2:43 pm

1 stop7h 43m

Simpson Bay Princess Juliana

Fri 5/30

1:35 pm-10:12 pm

1 stop9h 37m

$805

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/16

9:42 am-2:00 pm

3 stops27h 18m

Simpson Bay Princess Juliana

Fri 5/23

3:05 pm-5:14 pm

3 stops27h 09m

$814

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 21 results

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

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Chicago 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 Chicago to St. Maarten

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

Currently, September is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $459). Flying from Chicago to St. Maarten in July is currently the most expensive (average of $675). 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.

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

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

Reviews of airlines servicing St. Maarten

See what other customers who have flown with Delta, Copa Airlines and United Airlines from Chicago to St. Maarten have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,898 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Copa Airlines

7.6

Good

1,400 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines

7.4

Good

8,615 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet

7.2

Good

2,789 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

What are the cheapest airlines to fly from Chicago to St. Maarten one-way?
To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $139. Delta flights start at $308 while deals on American Airlines start at $378 one-way.
What are the cheapest flights from Chicago to St. Maarten?
Looking at all options, your cheapest flight can be booked for $757. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $337 on average our data indicates $1,043 when flying from Chicago to St. Maarten.
Can I find deals for flights from Chicago to St. Maarten that include hotel bookings?
Yes. In addition to deals on Chicago to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to St. Maarten?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to St. Maarten.
Can I find deals for business class flights from Chicago to St. Maarten?
Yes. Cheapflights offers flight deals from Chicago to St. Maarten 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 Chicago to St. Maarten?
Currently, September is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $459). Flying from Chicago to St. Maarten in July is currently the most expensive (average of $675). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to St. Maarten

O'Hare Intl to Luis Munoz Marin Intl flights

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Midway to Nassau flights

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O'Hare Intl to George Town flights

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O'Hare Intl to Puerto Plata flights

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O'Hare Intl to Providenciales flights

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Midway to Providenciales flights

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Moline to Montego Bay flights

St. Louis to Oranjestad flights

St. Louis to George Town flights

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O'Hare Intl to Road Town flights

Midway to Simpson Bay flights

St. Louis to Castries flights

O'Hare Intl to St. John's flights

O'Hare Intl to Gregory Town flights

Midway to George Town flights

O'Hare Intl to Santiago de los Caballeros flights

O'Hare Intl to Port of Spain flights

St. Louis to Simpson Bay flights

O'Hare Intl to Basseterre flights

O'Hare Intl to St. George's flights

Moline to Punta Cana flights

O'Hare Intl to Freeport flights

O'Hare Intl to Castries flights

St. Louis to Willemstad flights

Top 4 airlines flying from Chicago to St. Maarten

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$325	Average$401	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$554	Average$799	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$603	Average$725	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$610	Average$896	FlexibilityNo cancel fee	On-time69%

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$139+ Cheap flights from Chicago (CHI) to St. Maarten

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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to St. Maarten with Cheapflights

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Cheap flight deals from Chicago to St. Maarten

Keep the following information in mind while searching for Chicago to St. Maarten flight deals. Data was last updated April 2, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Find flight deals from Chicago to St. Maarten

Cheapest flights from Chicago to St. MaartenExplore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2025.

Explore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2025.

Cheapflights Fare Finder

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

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

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

Cheapflights Insights

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

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

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

Find hourly flight availability from Chicago to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 2, 2025.

Reviews of airlines servicing St. Maarten

See what other customers who have flown with Delta, Copa Airlines and United Airlines from Chicago to St. Maarten have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to St. Maarten. 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 Chicago to St. Maarten one-way?

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

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

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

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

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

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 Chicago to St. Maarten

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

Top 4 airlines flying from Chicago to St. Maarten

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Cheapest flights from Chicago to St. Maarten
Explore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2025.