Are direct Chicago to St Maarten flights available?
No non-stop option appears in the current route snapshot. Available itineraries may include one or more stops; use the Stops filter to compare them.
ORD to SXM
Chicago to St Maarten Flights from US$371 + Up to 20% Off
Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.
Live fares from the airlines
No hidden charges
Transparent cancellation policy
24×7 booking support
Cheapest fareUS$371Delta Air Lines
Fastest7h 22mgate to gate
Options today53flights on this route
Live flights for Tue, 18 Aug 2026
Review fares, stops, timings and baggage. Use Search or View all flights for the complete search result.
Showing flight options for the selected travel date.
Currency: USD
Delta Air Lines
DL-1716
13:59
2026-08-18
CHICAGO (ORD)
O Hare International
O Hare International22H :54 M
2 Stops
DTW
· 3h 16m Detroit (DTW), United States
ATL
· 11h 56m Atlanta (ATL), United States
13:53
2026-08-19
St Maarten (SXM)
Princess Juliana
Princess Juliana
FLYX20 Applied
$363
$371
Delta Air Lines
DL-2039
06:59
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International29H :54 M
2 Stops
DTW
· 10h 22m Detroit (DTW), United States
ATL
· 11h 56m Atlanta (ATL), United States
13:53
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$369
$377
Delta Air Lines
DL-4456
08:48
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International28H :05 M
2 Stops
DTW
· 8h 26m Detroit (DTW), United States
ATL
· 11h 56m Atlanta (ATL), United States
13:53
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$369
$377
Delta Air Lines
DL-3673
11:22
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International25H :31 M
2 Stops
DTW
· 5h 52m Detroit (DTW), United States
ATL
· 11h 56m Atlanta (ATL), United States
13:53
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$369
$377
Delta Air Lines
DL-2358
17:20
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International19H :33 M
2 Stops
DTW
· 9h 28m Detroit (DTW), United States
ATL
· 2h 37m Atlanta (ATL), United States
13:53
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$369
$377
American Airlines
AA-2984
05:00
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International7H :22 M
1 Stop
MIA
· 0h 53m Miami (MIA), United States
13:22
2026-08-18
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-2984
05:00
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International9H :39 M
1 Stop
MIA
· 3h 13m Miami (MIA), United States
15:39
2026-08-18
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-2842
05:05
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International9H :34 M
2 Stops
CLT
· 0h 58m Charlotte (CLT), United States
MIA
· 1h 07m Miami (MIA), United States
15:39
2026-08-18
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-2452
06:00
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International8H :39 M
1 Stop
MIA
· 2h 13m Miami (MIA), United States
15:39
2026-08-18
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-1875
06:59
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International7H :40 M
1 Stop
MIA
· 1h 10m Miami (MIA), United States
15:39
2026-08-18
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-512
15:05
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International21H :17 M
2 Stops
LGA
· 1h 06m New York (LGA), United States
MIA
· 11h 15m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-2840
15:25
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International20H :57 M
2 Stops
PHL
· 1h 08m Philadelphia (PHL), United States
MIA
· 10h 52m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-1809
16:00
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International20H :22 M
2 Stops
PHL
· 0h 31m Philadelphia (PHL), United States
MIA
· 10h 52m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-3188
16:53
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International19H :29 M
2 Stops
CLT
· 1h 26m Charlotte (CLT), United States
MIA
· 10h 24m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-2323
17:59
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International18H :23 M
1 Stop
MIA
· 11h 43m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-1159
18:59
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International17H :23 M
1 Stop
MIA
· 10h 49m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$424
$432
American Airlines
AA-2452
06:00
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International30H :22 M
1 Stop
MIA
· 23h 53m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-1784
06:49
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International29H :33 M
2 Stops
CLT
· 19h 25m Charlotte (CLT), United States
MIA
· 2h 38m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-1784
06:49
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International31H :50 M
2 Stops
CLT
· 21h 10m Charlotte (CLT), United States
MIA
· 3h 08m Miami (MIA), United States
15:39
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-411
07:30
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International28H :52 M
2 Stops
CLT
· 2h 54m Charlotte (CLT), United States
MIA
· 18h 20m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-411
07:30
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International31H :09 M
2 Stops
CLT
· 2h 54m Charlotte (CLT), United States
MIA
· 20h 40m Miami (MIA), United States
15:39
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-1250
08:37
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International27H :45 M
1 Stop
MIA
· 21h 10m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
Recommended hotels in St Maarten
Stay options near the arrival city for the same travel date.
No hotel result available
Open hotel search to check current stays for this destination.
American Airlines
AA-1250
08:37
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International30H :02 M
1 Stop
MIA
· 23h 30m Miami (MIA), United States
15:39
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-2080
08:54
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International27H :28 M
2 Stops
CLT
· 17h 17m Charlotte (CLT), United States
MIA
· 2h 38m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-2080
08:54
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International29H :45 M
2 Stops
CLT
· 21h 02m Charlotte (CLT), United States
MIA
· 1h 07m Miami (MIA), United States
15:39
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
American Airlines
AA-3056
09:55
2026-08-18
CHICAGO (ORD)O Hare International
O Hare International26H :27 M
1 Stop
MIA
· 19h 52m Miami (MIA), United States
13:22
2026-08-19
St Maarten (SXM)Princess Juliana
Princess Juliana
FLYX20 Applied
$430
$437
No flights match the selected filters. Clear filters or open full search.
Fare highlights
Selected flight highlights for 18 Aug 2026.
Lowest fare
$371
Delta Air Lines
13:59
Earliest departure
$432
American Airlines
05:00
Shortest duration
$432
American Airlines
05:00
Night
00:00-05:59
$432
American Airlines at 05:00
Morning
06:00-11:59
$377
Delta Air Lines at 06:59
Afternoon
12:00-17:59
$371
Delta Air Lines at 13:59
Evening
18:00-23:59
$432
American Airlines at 18:59
Chicago to St Maarten flight booking guide
Quick answers to the most common questions about flying Chicago to St Maarten.
Best time or month to book
There is no permanently cheapest month because airline inventory changes continuously. As a practical starting point, compare nearby dates and begin checking international trips 6–12 weeks before departure; peak holidays may need earlier booking.
Cheapest days for this route
Among the dates currently shown, Tuesday has the lowest displayed fare at $371. This is a live snapshot, not a guaranteed weekly rule.
Baggage rules
Allowance is fare-specific, not just airline-specific. Current cards show examples such as 0 Pieces, 1 Pieces check-in baggage. Open the fare choices and verify cabin/check-in baggage before continuing.
Cancellation and refund explanation
Refundable and non-refundable labels are shown on each card. Exact airline cancellation charges, no-show rules and refund timelines are verified for the selected fare before booking; promotional discounts and applicable charges are adjusted from any refund.
Secure booking support
FlyX rechecks the live fare before payment, shows the payable amount and provides 24×7 booking support. Payment, refund, cancellation and help links are available in the footer.
Airlines flying from Chicago to St Maarten
Compare fares, stops, baggage and refundability across the airlines flying this route.
American Airlines Chicago to St Maarten flights
American Airlines cheap flights Chicago to St Maarten
Fares start from $432 on this route.
Chicago to St Maarten American Airlines flight schedule
40 departures — compare timings in the list above.
Delta Air Lines Chicago to St Maarten flights
Delta Air Lines cheap flights Chicago to St Maarten
Fares start from $371 on this route.
Chicago to St Maarten Delta Air Lines flight schedule
10 departures — compare timings in the list above.
Chicago to St Maarten flight details
| Cheapest fare | US$371 · Tue, 18 Aug |
|---|---|
| Fastest flight duration | 7h 22m · American Airlines |
| First departure of the day | 05:00 · American Airlines |
| Last departure of the day | 20:53 · American Airlines |
| Flights currently available | 53 |
| Popular airlines on this route | American Airlines, Delta Air Lines, Klm Royal Dutch, Air France |
| Airport codes | Chicago–ORD, St Maarten–SXM |
Fares and timings are indicative — the exact price is confirmed with the airline when you search.
Chicago to St Maarten flight schedule, timing and fares
Chicago to St Maarten flight schedule and timing
Around 53 flights operate on this route. Departures run through the day — the first flight leaves around 05:00 and the last around 20:53. The fastest flight takes about 7h 22m.
Morning vs evening Chicago–St Maarten fares
Lowest fare by departure window: Afternoon from $371, Morning from $377, Night from $432, Evening from $432. Early-morning and late-night flights are often cheaper than peak daytime slots.
What is today’s lowest airfare from Chicago to St Maarten?
The lowest fare we are currently showing is US$371, on a Tuesday departure. Airfares change through the day, so search your dates for the exact price.
Should I book one-way or round-trip for Chicago to St Maarten?
Domestic fares are usually priced per leg, so two one-ways often cost about the same as a round-trip and keep your return date flexible. Round-trip is worth choosing when you want a single PNR for both legs, and eligible coupons like FLYX20 apply either way.
Which airlines should I consider for Chicago to St Maarten?
American Airlines (40 flights, from $432), Delta Air Lines (10 flights, from $371), Klm Royal Dutch (2 flights, from $4,706), Air France (1 flight, from $5,145). Compare fare type, baggage and refundability — the cheapest airline is not always the best value for your dates.
Web check-in for your Chicago to St Maarten flight
Most airlines open web check-in 24–48 hours before departure on their own website or app using your PNR. Checking in early lets you pick better seats free of charge on many fares; FlyX also links every booking’s airline check-in page from Web Check-in.
How to book a Chicago to St Maarten flight on FlyX
- 1Enter your travel details
Choose one-way or round-trip, pick your dates and travellers in the search form above.
- 2Compare live results
Sort or filter the Chicago–St Maarten results by price, departure time, stops and airline.
- 3Open the fare choices
Check baggage allowance and refundability for each fare type before continuing.
- 4Review the final price
FlyX rechecks the live fare with the airline; any eligible coupon is applied automatically.
- 5Pay securely
UPI, cards, net banking and wallets supported; your e-ticket is emailed within minutes.
Chicago and St Maarten travel guide
About Chicago
Chicago, the most populous city in Illinois and the third most populous in the United States, is a bustling metropolis known for its iconic skyline, vibrant arts scene, and diverse neighborhoods. Often referred to as the Windy City, Chicago offers a blend of architectural marvels, cultural landmarks, and a dynamic urban atmosphere. From world-class museums to sandy beaches along Lake Michigan, Chicago is a city that captivates visitors with its charm and energy.
Read more about Chicago
Airports
Chicago is served by two major airports:
• O'Hare International Airport (ORD) - Located approximately 18 miles northwest of downtown Chicago
• Chicago Midway International Airport (MDW) - Situated about 10 miles southwest of the city center
Hotels and Restaurants
Chicago offers a wide range of accommodation options to suit every budget:
• The Ritz-Carlton Chicago - Luxury hotel with stunning views of Lake Michigan
• The Drake Hotel - Historic hotel with elegant rooms and top-notch service
• Hotel Lincoln - Boutique hotel with a rooftop bar and quirky decor
• HI Chicago Hostel - Budget-friendly option with modern amenities
When it comes to dining, Chicago is a food lover's paradise:
• Alinea - Renowned for its innovative and artistic dishes
• Lou Malnati's Pizzeria - Famous for its deep-dish pizza
• Girl & the Goat - Popular spot for creative small plates
• Portillo's - Iconic for its Chicago-style hot dogs
Transportation
Getting around Chicago is convenient with various transportation options:
• Chicago Transit Authority (CTA) - Extensive network of buses and 'L' trains
• Metra - Commuter rail system connecting the suburbs to the city
• Taxis and Rideshares - Widely available across the city
• Divvy Bikes - Bike-sharing program with numerous docking stations
Must-See Places
Chicago boasts numerous attractions that should not be missed:
• Millennium Park - Home to the iconic Cloud Gate sculpture (The Bean)
• The Art Institute of Chicago - Houses an impressive collection of artworks
• Navy Pier - Entertainment hub with rides, restaurants, and shops
• Willis Tower Skydeck - Offers breathtaking views from the 103rd floor
• Museum Campus - Includes the Field Museum, Shedd Aquarium, and Adler Planetarium
Climate
Chicago experiences a continental climate with distinct seasons:
• Winter (December to February) - Cold and snowy, ideal for winter sports
• Spring (March to May) - Mild temperatures and blooming flowers
• Summer (June to August) - Warm and humid, perfect for outdoor activities
• Autumn (September to November) - Cool and crisp, great for sightseeing
The best time to visit Chicago is during late spring to early autumn when the weather is pleasant and outdoor events are in full swing. Whether you're exploring its architectural wonders, indulging in its culinary delights, or enjoying its vibrant cultural scene, Chicago promises an unforgettable experience.
Why book your Chicago to St Maarten flight with FlyX?
If you are looking for Chicago to St Maarten flight tickets at the best possible fare, FlyX keeps the process simple and transparent. Enter your dates and travellers, compare live fares across every major airline on this route, and filter by price, departure time, stops or airline to find the flight that actually fits your plan. Every fare you see is rechecked live with the airline before payment, so the price you approve is the price you pay — no hidden charges added at checkout.
And that is not all — eligible discounts like FLYX20 are applied automatically on the review page, payments run over 256-bit SSL with UPI, cards, net banking and wallets, and our 24x7 support team backs every booking as an IATA-accredited travel company. Refund and cancellation rules are shown clearly for each fare before you pay, and your e-ticket lands in your inbox within minutes. So why wait? Book your Chicago to St Maarten flight on FlyX and take off with genuine savings today.
Chicago to St Maarten flight offers & coupon codes
| Coupon code | Offer | Max saving |
|---|---|---|
| FLYX20 | Up to 20% Off on Flights | ₹1,500 |
Your discount is applied automatically on the review page before you pay. View full terms.
Frequently asked questions - Chicago to St Maarten flights
Is it worth booking Chicago to St Maarten flights in advance?
Yes, booking flights in advance helps you secure cheap flight tickets. Comparing air ticket prices 3–4 weeks early gives you better visibility of airline timings, baggage policies, and fare rules before high-demand periods push prices up.
How far is Chicago from St Maarten by air?
The flying distance depends on the routing selected by the airline. Live flight cards show duration and stop details for each result.
Are there non-stop flights from ORD to SXM?
Non-stop flight availability depends on the airline schedule and departure date. You can filter the live search results by stops to view direct flights, one-stop connections, and transit flights instantly.
Why does the price change after clicking Book Now?
Airline seat inventory and airfares change dynamically in real-time. Selecting 'Book Now' runs a live fare verification check to ensure you get the most accurate price before final booking confirmation.
Can I compare nearby dates?
Yes, you can easily compare flights for nearby dates. Select any date on the date calendar strip to refresh the fares, compare air ticket pricing, and choose the most budget-friendly travel day.
Chicago to St Maarten - what to expect when booking
The ORD to SXM cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.
Before you book
Compare nearby dates
The date strip opens the complete search result for the route and selected date.
Use filters
Shortlist by price, stops, departure time and refundable fare preference.
Check fare choices
Continue to Booking opens the verified fare choices, including baggage and refundability, before review.
Book Cheapest Flight from Chicago to St Maarten on FlyX
Securing the best airfare from Chicago to St Maarten is all about planning. FlyX's real-time fare tracking system allows you to check flight options and lock in the lowest ticket prices before they rise:
- Book at least 3-4 weeks in advance to secure the most competitive Chicago to St Maarten airfares.
- Consider traveling mid-week (Tuesdays or Wednesdays) to bypass weekend pricing surges.
- Early morning or late-night departure flights consistently offer lower fares than afternoon slots.
- Use our live calendar view above to easily spot fare changes on nearby dates.
Find the Lowest airfare from Chicago to St Maarten
| Cheapest Fare | Fare | Date | Airline | Departure |
|---|---|---|---|---|
| Lowest Airfare Today | $371 | 18/08/2026 | Delta Air Lines | 13:59 |
| Cheapest Airfare Within 30 Days | $364 | 29/08/2026 | Delta Air Lines | 13:59 |
| Cheapest Airfare Within 90 Days | $353 | 28/10/2026 | Delta Air Lines | 13:59 |
Book Chicago to St Maarten Flight Tickets on FlyX
Planning to fly from Chicago to St Maarten? FlyX lets you compare flight rates, airline timings, layovers, and baggage allowances all in one simple list. From quick non-stop routes to flexible connecting options, finding and booking cheap air tickets has never been easier.
Chicago to St Maarten Flight Schedule and Timing
Around 53 flights operate on this route, providing plenty of choices for your travel window. The earliest morning flight departs from Chicago at 05:00, while the last night flight leaves at 20:53. Flights depart from O Hare International and land at Princess Juliana.
Flight Route Details & Analysis
| Flight Details | Information |
|---|---|
| Route | Chicago to St Maarten |
| Flight Duration | 7H :22 M - 31H :50 M |
| Airport Codes | Chicago - ORD, St Maarten - SXM |
| Total Flights Available | 53 flights (0 direct) |
| First Flight Departure | Departs at 05:00 |
| Last Flight Departure | Departs at 20:53 |
| Early Morning Flights (12 AM - 8 AM) | 11 direct/indirect flights |
| Morning Flights (8 AM - 12 PM) | 10 direct/indirect flights |
| Afternoon Flights (12 PM - 4 PM) | 11 direct/indirect flights |
| Evening Flights (4 PM - 8 PM) | 19 direct/indirect flights |
| Night Flights (8 PM - 12 AM) | 2 direct/indirect flights |
Airport Information & Terminals
ORD: Chicago airport system. Chicago flights commonly use O'Hare or Midway. O'Hare is a huge hub with rail access; Midway can be easier for some city-side trips. Winter weather and traffic should be part of the booking decision.
SXM: St. Marteen airport. Airport access in St. Marteen depends on arrival time, terminal, hotel location and local traffic. Confirm the airport name on the ticket, then choose between official taxi, app cab, airport bus, rail or hotel transfer based on luggage and time of day.
SXM: St. Marteen airport. Airport access in St. Marteen depends on arrival time, terminal, hotel location and local traffic. Confirm the airport name on the ticket, then choose between official taxi, app cab, airport bus, rail or hotel transfer based on luggage and time of day.
