$128 Find Cheap Flights from Chicago O'Hare Airport to Simpson Bay - Compare and Save

Among airlines operating Chicago O'Hare Intl Airport to Simpson Bay flights:

• United Airlines: offers free seat selection
• American Airlines: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

2 airlines operate flights between Chicago O'Hare Intl Airport and Simpson Bay. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flights from Chicago O'Hare Intl Airport to Simpson Bay usually depart from Chicago O'Hare Intl (ORD) and arrive at Simpson Bay Princess Juliana (SXM).

Here are some options for this route, based on selected ticket types and cabin classes:

• American Airlines: a cabin bag and a checked bag in Economy Class
• Alaska Airlines: a cabin bag and a checked bag in Business Class
• United Airlines: a cabin bag and a checked bag in Business Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Two cabin classes are available on flights from Chicago O'Hare Intl Airport to Simpson Bay:

• Economy Class
• Business Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $418 round-trip via Fort Lauderdale (FLL), compared to $795 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Airbus A319 variants.

One-stop flights from Chicago O'Hare Intl Airport to Simpson Bay most commonly connect through:

• Fort Lauderdale (FLL) - 39% of one-stop connections
• Miami (MIA) - 35% of one-stop connections
• Charlotte Douglas (CLT) - 12% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 7% of one-stop connections

Fort Lauderdale (FLL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 33% on the Chicago O'Hare Intl Airport to Simpson Bay route. Monday is the cheapest departure day at $482 round-trip on average, while Saturday is the most expensive at $717, a difference of $235. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago O'Hare Intl Airport to Simpson Bay route, 25% of flights were delayed in the past 3 months, with delays averaging 1 hour 57 minutes.

These are the earliest and latest flight times available from Chicago O'Hare Intl Airport to Simpson Bay:

• Earliest: departs at 8:15 am and lands at 1:33 pm
• Latest: departs at 8:40 am and lands at 1:58 pm.

The flight takes about 5h 18m.

Last-minute fares on this route - booked within 2 weeks of departure - run 19% above the route average of $668. Book 8 weeks before departure for the lowest fares.

A nonstop flight from Chicago O'Hare Intl Airport to Simpson Bay takes 5h 18m, covering 2,204 miles.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

One-way fares from Chicago O'Hare Intl Airport to Simpson Bay are currently lower than usual. Average one-way flight prices are about $220, which is 33% below the typical average for this route.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 7h 39m, compared with 8h 10m via Orlando (MCO) and 8h 19m via Atlanta Hartsfield-Jackson (ATL).

Simpson Bay is 1 hour ahead of Chicago O'Hare Intl Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
• Ace
• Right Cars
• Europcar
• Budget
• Alamo

Round-trip flights from Chicago O'Hare Intl Airport to Simpson Bay range from $517 to $797, with an average of $668 over the past 12 months. Anything below $517 counts as a good deal.

American Airlines is the only airline on the Chicago O'Hare Intl Airport to Simpson Bay route offering in-flight Wi-Fi. Pricing depends on fare class.