Chicago to Sint Maarten MDW, ORD, RFD → SXM
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Princess Juliana International Airport (SXM)
The cheapest one-way found recently is $279 with United Airlines, 30 Dec, found yesterday.
One-way
The cheapest one-way fare on each of 3 departure dates is usually $220 to $428.
Cheapest one-way found recently
$279
30 Dec · United Airlines
O'Hare International Airport (ORD) → Princess Juliana International Airport (SXM)
Leaves 5:56 p.m. · 43 h 49 min trip
2 stops
found yesterday
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$279 30 Decfound yesterdayOpen this trip
$161 27 Novfound 2 days agoOpen this trip
What have prices looked like?
Over 2 days, 17 Oct to 18 Oct, the cheapest one-way we saw each day was $161.
At $279, the cheapest one-way found recently is above that range.
2 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 3 departure dates from 27 Nov to 30 Dec, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 30 Dec to compare.
Every date we hold
5 fares on 3 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 27 Nov | $161 | Air Canada | O'Hare International Airport (ORD) → Princess Juliana International Airport (SXM) | 1 stop | found 2 days ago | Open this trip |
| 25 Dec | $576 | Southwest Airlines | Chicago Midway International Airport (MDW) → Princess Juliana International Airport (SXM) | 1 stop | found 2 days ago | Open this trip |
| 30 Dec | $279 | United Airlines | O'Hare International Airport (ORD) → Princess Juliana International Airport (SXM) | 2 stops | found yesterday | Open this trip |
Which month looks cheapest?
November 2026 is the cheapest month — from $161.
Airlines on the cheapest dates: Air Canada, Southwest Airlines, United Airlines.
Premium cabin fares from Chicago to Sint Maarten
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 30 Dec in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Sint Maarten?
One-way
Not enough history yet: we have 2 days of one-way prices, 17 Oct to 18 Oct, and compare booking times once 3 booking ranges have 7 days each.
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Chicago → Saint Martin
9 km from Sint Maarten
$1,917
19 Dec – 3 Jan 2027 · ORD → SFG · out 3 stops, back 2 stops
found today
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest one-way found recently is for 30 Dec. A live search on this page shows what those dates cost now, for one adult in economy.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work