Cheap flights from Chicago to Simpson Bay from $132

In general, February is the cheapest month to fly from Chicago to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $512. If you aren’t able to travel to Simpson Bay during the month of February, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $566.

Our data shows that Sunday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $553. Flights from Chicago to Simpson Bay on a Saturday will generally be more expensive and average around $782. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago - Simpson Bay Princess Juliana flight prices

You are more likely to see cheaper flights to Simpson Bay from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $676 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Chicago for as low as $548 on momondo.

There are 4 cabin classes available to choose from on Chicago to Simpson Bay flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 10% on your flight if you consider stops on a Chicago to Simpson Bay flight.

Air Canada, JetBlue, and Southwest are the most popular carriers operating from Chicago to Simpson Bay Princess Juliana

American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Simpson Bay from Chicago according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

Historically, on average around 25% of flights between Chicago and Simpson Bay have experienced a delay on any given week. The average delay length over the past 12 months has been 105 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

Washington, D.C. (IAD) was the most common stop: 31% of momondo users choosing 1-stop flights on this route connected there.

Flights via Washington, D.C. (IAD) offer the lowest average round-trip price of $587.

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 6h 59m.

Miami (MIA) has the shortest average layover time for this route: 1h 23m.