Cheap flights from Chicago to the U.S. Virgin Islands from $128

In general, May is the cheapest month to fly from Chicago to U.S. Virgin Islands. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $370. If you aren’t able to travel to U.S. Virgin Islands during the month of May, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $529.

According to our data, Thursday is the cheapest day to fly to U.S. Virgin Islands from Chicago. The lowest ticket price found for a Thursday departure recently was $610. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $790.

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

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

There are 2 cabin classes available to choose from on Chicago to U.S. Virgin Islands 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 U.S. Virgin Islands flight.

Spirit Airlines, Southwest, and Delta are the most popular carriers operating from Chicago to U.S. Virgin Islands

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to U.S. Virgin Islands from Chicago according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to U.S. Virgin Islands. Keep in mind that there are 4 different airlines that fly to U.S. Virgin Islands on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between Chicago and U.S. Virgin Islands 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.

2 flights are operational daily from Chicago to U.S. Virgin Islands as of March 2026. The most popular departure time for this route is 8:00AM, with 100% of flights per day taking off at noon.

15 flights are operational weekly from Chicago to U.S. Virgin Islands as of March 2026. The most popular departure day for this route is Sat, with 20% of flights per week taking off on this day.