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.
SXMORDFri, 30 Oct
Fare checked before payment All fees shown upfront Transparent cancellation policy 24×7 booking support
Lowest fareUS$271Air Canada
Fastest8h 59mgate to gate
Options found48flights on this route
Find your flightSXM → ORD
Available Flights & Fares
Compare fares, timings and baggage. Pick the flight that suits your trip.
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Refundable
Fare Type
AirLine Private
0 Pieces 2 Pieces
$401
Flight DetailsSXM to ORD - 19H :31 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesRefundable fare. Final rules are verified before booking.
AA
American Airlines
AA-3316
16:39
2026-10-30
St Maarten (SXM)Princess Juliana
29H :51 M
1 Stop
MIA
· 22h 51m Miami (MIA), United States
21:30
2026-10-31
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$356
Flight DetailsSXM to ORD - 29H :51 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Refundable
Fare Type
AirLine Private
0 Pieces 2 Pieces
$401
Flight DetailsSXM to ORD - 29H :51 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesRefundable fare. Final rules are verified before booking.
United Airlines
UA-1880
13:52
2026-10-30
St Maarten (SXM)Princess Juliana
9H :26 M
1 Stop
EWR
· 1h 42m New York (EWR), United States
22:18
2026-10-30
CHICAGO (ORD)O Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
$361
Flight DetailsSXM to ORD - 9H :26 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Refundable
Fare Type
AirLine Private
0 Pieces 1 Pieces
$421
Flight DetailsSXM to ORD - 9H :26 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesRefundable fare. Final rules are verified before booking.
United Airlines
UA-1880
13:52
2026-10-30
St Maarten (SXM)Princess Juliana
11H :09 M
1 Stop
EWR
· 3h 23m New York (EWR), United States
00:01
2026-10-31
CHICAGO (ORD)O Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
$361
Flight DetailsSXM to ORD - 11H :09 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Refundable
Fare Type
AirLine Private
0 Pieces 1 Pieces
$421
Flight DetailsSXM to ORD - 11H :09 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesRefundable fare. Final rules are verified before booking.
No flights match the selected filters. Clear filters or open full search.
Airfare Highlights
From flights departing on Fri, 30 Oct 2026.
Lowest fare$271Air Canada15:45
Earliest departure$361United Airlines13:52
Shortest duration$356American Airlines16:39
Night
00:00-05:59
No optionOpen full search for moreMorning
06:00-11:59
No optionOpen full search for moreAfternoon
12:00-17:59
$271Air Canada at 15:45Evening
18:00-23:59
No optionOpen full search for more
Departure & Arrival Airport Details
St Maarten (SXM)
Princess Juliana
Netherlands Antilles
Chicago (ORD)
O Hare International
USA
Flights shown for 30 Oct 2026. View all flights opens the complete search result.
Smart travel dates
Holidays and peak dates for Chicago
Fares and hotel rates usually run higher around these dates. Booking earlier or moving your trip by a day or two often costs less.
Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).
12OctColumbus DayMondayPeak
12OctColumbus DayMondayPeak
12OctIndigenous Peoples' DayMondayPeak
11NovVeterans DayWednesdayPeak
26NovThanksgiving DayThursdayPeak
25DecChristmas DayFridayPeak
Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here, so check the exact date for your travel year.
Compare your journey
How to travel St Maarten to Chicago
Ways to make this trip that you can book on FlyX, compared by price and journey time.
OptionFromJourney timeAvailabilityAction
Connecting flight₹26,191Longer, includes a stop48 options
4 airlines operate this route.
Road distance and coach duration are approximate estimates from the air distance, not a timetable.
Airlines flying from St Maarten to Chicago
Compare fares, stops, baggage and refundability across the airlines flying this route.
AM
American Airlines Flights
from $35416 flights
Fares from
$354
Non-stop
None in these results
Departures
16 in the list above
UN
United Airlines Flights
from $36114 flights
Fares from
$361
Non-stop
None in these results
Departures
14 in the list above
AI
Air Canada Flights
from $27112 flights
Fares from
$271
Non-stop
None in these results
Departures
12 in the list above
DE
Delta Air Lines Flights
from $3016 flights
Fares from
$301
Non-stop
None in these results
Departures
6 in the list above
Route Overview & Flight Facts
Fastest flight duration
8h 59m · American Airlines
First departure of the day
13:52 · United Airlines
Last departure of the day
16:39 · American Airlines
Flight options found
48
Airport codes
St Maarten–SXM, Chicago–ORD
Fares and timings are indicative. The exact price is confirmed with the airline when you search.
Flight Schedule, Timings & Airfare Insights
Daily Flight Schedule & Travel Duration
The search for Fri, 30 Oct found 48 flight options. The first flight leaves around 13:52 and the last around 16:39. The fastest flight takes about 8h 59m.
Cheapest Airfare & Best Time to Book
Search your travel dates to compare current fares. Prices change with airline seat availability.
One-Way vs Round-Trip Fare Comparison
Compare the complete cost and conditions of both options for your dates. A round-trip can have different fare and change rules from two one-way tickets. One booking may contain multiple airline PNRs; confirm baggage transfer and connection protection for separate tickets.
Online Web Check-In & Boarding Pass
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How to Book Cheap Flights on FlyX
1
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2
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Sort or filter the St Maarten–Chicago results by price, departure time, stops and airline.
3
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Check baggage allowance and refundability for each fare type before continuing.
4
Review the final price
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5
Pay securely
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Destination & City Travel Guide
About Chicago
Chicago’s downtown Loop puts Millennium Park, the Art Institute and the Riverwalk within a manageable area. The lakefront creates a second axis for walking, while neighbourhoods farther out need transit time of their own. Passengers landing at O’Hare may be changing flights or visiting relatives in the wider region, so check whether an overnight hotel is near the airport or downtown. The CTA Blue Line runs from the airport into the city and avoids the road congestion that can affect a taxi.
Read more about Chicago
Tips for travellers from India
The Loop is useful for the Art Institute, Millennium Park and central rail links, while a hotel near O’Hare serves an early flight or suburban appointment. These bases are a substantial distance apart. The CTA Blue Line reaches the airport from downtown, but passengers arriving at Terminal 5 first need the airport connection to the main rail-access area. The airport train and an intercity rail departure from Union Station are separate arrangements.
Air India uses Terminal 5. United domestic flights and international departures use Terminal 1, while many international arrivals are processed through Terminal 5, so an onward connection can involve a building change. In the city, pair the Art Institute with Millennium Park rather than crossing to a distant neighbourhood between them. The Riverwalk offers another central route, while the lakefront extends far beyond the downtown section. The Obama Presidential Center opened to the public in June 2026 in Jackson Park, creating a museum outing on the South Side rather than another stop beside the Loop. Plan that visit as its own district trip. A river architecture cruise also has a specific departure dock, which should be matched to the walking route. Choose between a museum-heavy day and a longer lakefront walk before booking several timed attractions.
Best time to visit Chicago
May to June or September to October, about 12–25°C, for river and lake walks.
Places to visit in Chicago
Millennium ParkArt Institute of ChicagoChicago RiverwalkNavy PierMuseum CampusDevon Avenue
How to reach Chicago
By Air: O’Hare International Airport (ORD) is about 27 km northwest of downtown Chicago; the CTA Blue Line takes about 45 minutes to the Loop. Taxis and booked cars also operate.
By Rail: Chicago Union Station serves intercity trains; the CTA Blue Line links O’Hare with downtown.
By Road: Airport taxis and app-based cars use expressways; intercity coaches use downtown stops.
What to do in Chicago
Walk from Millennium Park to the Art Institute.
Follow the Chicago Riverwalk.
Take an architecture cruise on the Chicago River.
Explore the lakefront around Museum Campus.
Chicago airport information
O’Hare International Airport (ORD). Air India operates from O’Hare Terminal 5. United uses Terminal 1 for domestic flights and international departures, while international arrivals without preclearance generally use Terminal 5.
Why Book Your Flight with FlyX?
Compare the available St Maarten to Chicago options by total price, stops, baggage and fare conditions. Search your dates for current availability, then review traveller details and the final price before paying.
Payment confirmation and ticket issuance are separate steps. If your booking is awaiting a PNR or ticket, follow its status and contact FlyX support when you need help. Your issued ticket contains the airline reference and itinerary. Change and cancellation charges depend on the purchased fare and any separately disclosed service fee.
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Frequently Asked Questions
Is it worth booking St Maarten to Chicago flights in advance?
There is no guaranteed cheapest booking window. Compare your planned dates early, check nearby dates and consider baggage, connection time and change conditions as well as price. On the St Maarten to Chicago dates shown on this page, the lowest fare is on a Friday at $271. This can change from week to week.
How far is St Maarten from Chicago by air?
The flying distance depends on the routing the airline selects. The flight cards above show duration and stop details for each result.
Are there non-stop flights from SXM to ORD?
Not on the dates shown here. Every St Maarten to Chicago option on this page has at least one stop. Non-stop service can differ by season and by day, so check nearby dates before you decide.
Which airlines fly St Maarten to Chicago?
American Airlines, United Airlines, Air Canada and Delta Air Lines are listed on this route for the dates shown here. Fares, baggage allowance and refund rules differ by airline and by fare type, so compare the fare conditions and not only the headline price.
How long is the flight from St Maarten to Chicago?
Every option on this page has at least one stop, and the shortest total journey time is about 8h 59m including the layover. Non-stop service on this route can vary by season and by day.
What is the cheapest St Maarten to Chicago flight fare?
The lowest St Maarten to Chicago fare on this page is $271. Fares on the same dates run up to $637, depending on airline, timing and fare type. Airline prices change often, so search your dates for the current fare.
What time do St Maarten to Chicago flights depart?
On the dates shown here, the first departure is around 13:52 and the last around 16:39, local time at St Maarten. Use the departure-time filter on the results above to narrow to a morning, afternoon or evening slot.
Why does the price change after clicking Book Now?
Airline seat inventory and fares change continuously. Selecting Book Now runs a live fare verification with the airline so the price you approve is the price you pay. If it has moved, you see the new figure before any payment.
Before you book this route
Check the airport codes SXM–ORD, local departure and arrival dates, and every connecting airport. Connections can have different document and baggage requirements from your final destination.
Where these fares come from
The fares, durations, stops and baggage shown here come from real airline search results for this route. They are examples for the dates on this page, not a full timetable and not a locked price. Run a search to see what is available for your own dates.
Fares shown are for departures on .
Check official travel requirements
Confirm passport, visa and transit rules for your nationality and full itinerary with the relevant government and operating airline. IATA travel-document information explains why requirements vary.
The SXM to ORD 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
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Lowest St Maarten to Chicago airfare, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare
$271
30/10/2026
Air Canada
15:45
Cheapest Airfare Within 30 Days
$266
07/11/2026
Air Canada
15:45
Cheapest Airfare Within 90 Days
$258
06/01/2027
Air Canada
15:45
Book St Maarten to Chicago Flight Tickets on FlyX
FlyX lists each St Maarten to Chicago flight in these results with its fare, departure time, stops, layover airport and baggage, so you can compare air tickets side by side. To find a cheap ticket, sort by price and check what baggage the fare includes. The fare is checked with the airline again before you pay.
St Maarten to Chicago Flight Schedule and Timing
The search for these dates returned 48 flight options. The first departure from St Maarten is at 13:52 and the last is at 16:39. Flights leave from Princess Juliana and land at O Hare International.
Flight Route Details & Analysis
Flight Details
Information
Route
St Maarten to Chicago
Flight Duration
8h 59m - 31h 22m
Airport Codes
St Maarten - SXM, Chicago - ORD
Total Flights Available
48 flights0 direct48 with layovers
First Flight Departure
Departs at 13:52
Last Flight Departure
Departs at 16:39
Early Morning Flights (12 AM - 8 AM)
No flights in this time slot
Morning Flights (8 AM - 12 PM)
No flights in this time slot
Afternoon Flights (12 PM - 4 PM)
41 flights0 direct41 with layovers
Evening Flights (4 PM - 8 PM)
7 flights0 direct7 with layovers
Night Flights (8 PM - 12 AM)
No flights in this time slot
Airport Information & Terminals
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.
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.
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St Maarten to Chicago
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Princess Juliana
O Hare International
