Cheap flights from Chicago to U.S. Virgin Islands

Flights overview

Useful information for finding cheap flights from Chicago to U.S. Virgin Islands and booking your next trip
Cheapest round-trip flights $520
United 1 stop 18 hr Sat, Jul 4 — Sat, Jul 11
The cheapest round-trip flight from Chicago to U.S. Virgin Islands is currently $520
Cheapest one-way flight $178
United 2 stops 14 hr Tue, Aug 4
The cheapest one-way flight from Chicago to U.S. Virgin Islands is currently $178
Cheapest nonstop flights $588
United Nonstop 6 hr Sat, Jul 4 — Sat, Jul 11
The cheapest nonstop round-trip flight from Chicago to U.S. Virgin Islands is currently $588
Last-minute weekend getaway $871
Southwest 1 stop 8 hr Sat, May 9 — Sun, May 10
The cheapest last-minute weekend getaway from Chicago to U.S. Virgin Islands is currently $871
Cheapest business class flights $1,100
American 1 stop 18 hr Thu, Jul 23 — Wed, Jul 29
The cheapest business class round-trip flight from Chicago to U.S. Virgin Islands is currently $1,100
Fastest flight 5 hr 1 min The fastest nonstop flight from Chicago to U.S. Virgin Islands takes 5 hr 1 min
Nonstop flights Some days There are direct flights on this route 1 days a week: Sat.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to U.S. Virgin Islands is typically October. The most expensive month to fly is typically May.
October
Cheapest
Typical prices: $275–445
May
Most expensive
Typical prices: $360–530

Popular airlines from Chicago to U.S. Virgin Islands

  • Southwest
    from $590
    Typical price: $610–1,300
    947 weekly connecting flights
    MDW, ORD - STT Every day
  • American
    from $580
    Typical price: $510–870
    617 weekly connecting flights
    ORD - STT Every day
  • Delta
    from $580
    Typical price: $650–1,350
    400 weekly connecting flights
    MDW, ORD - STT Every day
  • United
    Nonstop
    from $580
    Typical price: $460–1,150
    1 weekly nonstop flight
    ORD - STT Every Sat
    178 weekly connecting flights
    ORD - STT Every day
  • JetBlue
    1 weekly connecting flight
    ORD - STT Every Fri

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Popular airports near U.S. Virgin Islands

  • Cyril E. King Airport (STT)
    Saint Thomas U.S. Virgin Islands 19 min 5 mi
  • St Thomas Island Charlotte Amalie SPB (SPB)
    Saint Thomas United States 12 min 2 mi

Frequently asked questions about flying from Chicago to U.S. Virgin Islands

The cheapest flights from Chicago to U.S. Virgin Islands are usually in October. Typical ticket prices in October range from $275 to $445.
The cheapest round-trip flight from Chicago to U.S. Virgin Islands recently found on Google Flights was with United from $520. The cheapest one-way flight was with United from $178.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to U.S. Virgin Islands is $590, flying from Jul 25 to Aug 3.
  • The cheapest American flight from Chicago to U.S. Virgin Islands is $580, flying from Jul 2 to Jul 9.
  • The cheapest Delta flight from Chicago to U.S. Virgin Islands is $580, flying from Jul 19 to Jul 28.
  • The cheapest United flight from Chicago to U.S. Virgin Islands is $580, flying from Jul 20 to Jul 27.
The cheapest round-trip flight from Chicago to U.S. Virgin Islands starts at $520 from Sat, Jul 4 to Sat, Jul 11. The cheapest one-way flight starts at $178 and departs on Tue, Aug 4.
5 hr 1 min is the shortest flight time from Chicago to U.S. Virgin Islands.
Peak travel season runs Dec–Mar, with hot daytime temperatures and breezy evenings. Apr–Aug is balmy and generally dry, while Aug–Nov is rainy/hurricane season. The islands’ biggest yearly events are the colourful Carnival celebrations, which are spread throughout the year, with St. Croix’s Crucian Christmas Carnival in Dec/Jan, St. Thomas Carnival in Apr/May and the St. John Festival in Jun/Jul.
It's easy to use Google Flights to find the cheapest days to fly from Chicago to U.S. Virgin Islands.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Chicago to U.S. Virgin Islands really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to U.S. Virgin Islands.

In terms of nonstop flights, United is the most popular. United offers 1 nonstop flights and 178 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .

In terms of flights, Southwest is the most popular. Southwest offers 947 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .

Other popular airlines flying from Chicago to U.S. Virgin Islands are:
  • American offers 617 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .
  • Delta offers 400 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .
  • JetBlue offers 1 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Cyril E. King Airport (STT) .
The number of connecting flights refers to distinct flights with at least one stop between Chicago and U.S. Virgin Islands.
The cheapest round-trip flight from Chicago to U.S. Virgin Islands recently found on Google Flights was with United from $520. The cheapest one-way flight was with United from $178.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to U.S. Virgin Islands is $590, flying from Jul 25 to Aug 3.
  • The cheapest American flight from Chicago to U.S. Virgin Islands is $580, flying from Jul 2 to Jul 9.
  • The cheapest Delta flight from Chicago to U.S. Virgin Islands is $580, flying from Jul 19 to Jul 28.
  • The cheapest United flight from Chicago to U.S. Virgin Islands is $580, flying from Jul 20 to Jul 27.
United flies direct from Chicago to U.S. Virgin Islands.
  • There are 1 United direct flights from Chicago to U.S. Virgin Islands per week. Flights are available on Saturday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Chicago and U.S. Virgin Islands at price $871 is offered by Southwest from Sat, May 9 to Sun, May 10.
United flies direct from Chicago to U.S. Virgin Islands.
  • There are 1 United direct flights from Chicago to U.S. Virgin Islands per week. Flights are available on Saturday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
Direct flights from Chicago to U.S. Virgin Islands are only available on Saturday.
The cheapest direct (nonstop) round-trip flights between Chicago and U.S. Virgin Islands start at $588 from Sat, Jul 4 to Sat, Jul 11 with United.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to U.S. Virgin Islands, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Chicago and U.S. Virgin Islands start at $1,100 from Thu, Jul 23 to Wed, Jul 29 with American.
The cheapest economy class round-trip flights between Chicago and U.S. Virgin Islands start at $520 from Sat, Jul 4 to Sat, Jul 11.
To book business class trips from Chicago to U.S. Virgin Islands, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Chicago and U.S. Virgin Islands starts at $871 from Sat, May 9 to Sun, May 10 with Southwest.
The cheapest last-minute deal between Chicago and U.S. Virgin Islands at price $871 is offered by Southwest from Sat, May 9 to Sun, May 10.
To find last-minute flight deals from Chicago to U.S. Virgin Islands, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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