Cheap flights from Chicago to Saint Thomas Island from $131

The month of January is another great option to travel to Saint Thomas Island, with average flight prices from Chicago averaging around $529.

On average, the least expensive day to fly to Saint Thomas Island from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $610. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Saint Thomas Island for around $790.

Fly from Chicago O'Hare Intl to Saint Thomas Island Cyril E King for the best Chicago - Saint Thomas Island Cyril E King flight prices

You are more likely to see cheaper flights to Saint Thomas Island from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Saint Thomas Island for around $636 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Saint Thomas Island from Chicago for as low as $525 on momondo.

There are 2 cabin classes available to choose from on Chicago to Saint Thomas Island Cyril E King 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 51% on your flight if you consider stops on a Chicago to Saint Thomas Island flight.

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from Chicago to Saint Thomas Island Cyril E King

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Saint Thomas Island from Chicago according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Saint Thomas Island. Keep in mind that there are 4 different airlines that fly to Saint Thomas Island on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between Chicago and Saint Thomas Island have experienced a delay on any given week. The average delay length over the past 12 months has been 131 minutes.

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

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

Miami (MIA) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

Flights via Fort Lauderdale (FLL) offer the lowest average round-trip price of $147.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 6h 51m.

Atlanta (ATL) has the shortest average layover time for this route: 1h 01m.

The number of flights available between Chicago and Saint Thomas Island is 1 per day as of March 2026. The most frequent departure time is 8:00AM, with 100% of daily flights leaving at noon.

As of March 2026, there are 12 flights per week flying from Chicago to Saint Thomas Island. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.