$163 Find Cheap Flights from Chicago to Simpson Bay - Compare and Save

These are the earliest and latest flight times available from Chicago to Simpson Bay:

• Earliest: departs at 8:06 am and lands at 1:23 pm
• Latest: departs at 8:40 am and lands at 1:57 pm.

The flight takes about 5h 17m.

Two cabin classes are available on flights from Chicago to Simpson Bay:

• Economy Class
• Business Class

A nonstop flight from Chicago to Simpson Bay takes 5h 17m, covering 2,188 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.

Round-trip flights from Chicago to Simpson Bay range from $542 to $796, with an average of $678 over the past 12 months. Anything below $542 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 18% above the $678 route average. Book 8 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $424 round-trip via Montreal Pierre Elliott Trudeau Intl (YUL), compared to $780 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $411 to $3,905. That means the highest observed fare was about 10x higher than the lowest one.

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

One-way fares from Chicago to Simpson Bay are currently lower than usual. Average one-way flight prices are about $259, which is 22% below the typical average for this route.

Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates averaging $40 for economy cars. Top options include:

• Right Cars
• Ace
• Budget
• Europcar
• Alamo

Flights from Chicago to Simpson Bay may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Simpson Bay Princess Juliana (SXM).

Morning flights have the fewest delays on this route.

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 to Simpson Bay route, 25% of flights were delayed in the past 3 months, with delays averaging 1h 57m.

One-stop flights from Chicago to Simpson Bay most commonly connect through:

• Miami (MIA) - 31% of one-stop connections
• Fort Lauderdale (FLL) - 31% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 14% of one-stop connections
• Charlotte Douglas (CLT) - 9% of one-stop connections

Yes. Flexible dates can save you up to 32% on flights from Chicago to Simpson Bay. Monday is the cheapest departure day at $505 round-trip on average, while Saturday is the most expensive at $737, a difference of $232.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

2 airlines operate flights between Chicago and Simpson Bay. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flying via Baltimore/Washington (BWI) gives the shortest average 1-stop total travel time at 7h 42m, compared with 7h 48m via Charlotte Douglas (CLT) and 8h 05m via Atlanta Hartsfield-Jackson (ATL).

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

Among airlines operating Chicago 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.

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 always check the fare details before booking.