$269 Find Cheap Flights from U.S. Virgin Islands to Chicago - Compare and Save

Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $486. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $606 on average.

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, when round-trip flights cost $395 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $580.

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Saint Thomas Island, which takes 5h 45m, and Christiansted, which takes 24h 26m.

There are around 5,973 direct flights from within U.S. Virgin Islands to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 51% of flights departing in the morning.

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago O'Hare Intl Airport. Instead, there are 4 medium-haul flights (3-6 hour flight duration), with the most arriving from Saint Thomas Island.

From the U.S. Virgin Islands, there are direct flights to Chicago O'Hare Intl Airport from 1 city. This city is Saint Thomas Island and there are 4 direct flights each week.