What is the cheapest month to book a flight from Chicago Midway Airport to U.S. Virgin Islands?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to U.S. Virgin Islands (average of $433). Flying from Chicago Midway Airport to U.S. Virgin Islands in June is currently the most expensive (average of $640). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How far in advance should I book a flight from Chicago Midway Airport to U.S. Virgin Islands?

Users have found that booking a flight from Chicago Midway Airport to U.S. Virgin Islands at least 48 days early can save you up to 72% on average compared to booking a flight this week. If booking 48 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to U.S. Virgin Islands for as little as $406 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $666 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago Midway Airport to U.S. Virgin Islands?

September can be a great time to fly to U.S. Virgin Islands from Chicago Midway Airport with a flight ticket averaging about $609. Cheapflights users have found deals in the month of September for as cheap as $179. The most expensive prices can be found in the month of March.

What is the cheapest time of day to fly from MDW to VI?

When flying from Chicago Midway Airport to U.S. Virgin Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Can I find deals for flights from Midway to U.S. Virgin Islands that include hotel bookings?

Yes. In addition to deals on Midway to U.S. Virgin Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Midway to U.S. Virgin Islands?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to U.S. Virgin Islands.

Can I find deals for business class flights from Midway to U.S. Virgin Islands?

Yes. Cheapflights offers flight deals from Midway to U.S. Virgin Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$557+ Flights from Chicago Midway Airport to the U.S. Virgin Islands

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Cheap flight deals from Midway to U.S. Virgin Islands

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$479 (Delta)
One-way from	$293 (Delta)
Popular in	March
Cheapest in	September
Average price	$589

Provider with most accurate pricing for Chicago (CHI)-Saint Thomas Island Cyril E King flight deals.

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Provider most trusted by Cheapflights users for Chicago (CHI)-Saint Thomas Island Cyril E King flights.

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From Chicago Midway to U.S. Virgin Islands

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One-way flight from Chicago Midway to U.S. Virgin Islands

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Highest demand for flights based on searches. 11% potential increase in price ($79 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).

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Average for round-trip flights in April 2025

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Find flight deals from Midway to U.S. Virgin Islands

Cheapest flights from Midway to U.S. Virgin Islands
Explore the most affordable flight options available from Midway to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

Tue 6/176:00 amMDW - STT

1 stop6h 49mDelta

Tue 6/243:00 pmSTT - MDW

1 stop7h 45mDelta

Deal found 4/17

$479

Sat 5/176:00 amMDW - STX

1 stop6h 38mDelta

Sat 5/243:00 pmSTX - MDW

1 stop7h 13mDelta

Deal found 4/17

$675

Best flights from Midway to U.S. Virgin Islands
Discover carefully curated flight deals from Midway to U.S. Virgin Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2025.

Tue 6/176:00 amMDW - STT

1 stop6h 49mDelta

Tue 6/243:00 pmSTT - MDW

1 stop7h 45mDelta

Deal found 4/17

$479

Sat 5/176:00 amMDW - STX

1 stop6h 38mDelta

Sat 5/243:00 pmSTX - MDW

1 stop7h 13mDelta

Deal found 4/17

$675

Last-minute flights from Midway to U.S. Virgin Islands
Discover last-minute flight deals from Midway to U.S. Virgin Islands. Data last updated April 17, 2025 and is based on user searches.

Thu 4/246:04 amMDW - STT

1 stop8h 01mDelta

Thu 5/11:55 pmSTT - MDW

1 stop9h 27mDelta

Deal found 4/17

$669

Wed 5/146:00 amMDW - STT

1 stop8h 10mDelta

Wed 5/212:51 pmSTT - MDW

1 stop7h 36mDelta

Deal found 4/15

$509

Sat 5/176:00 amMDW - STX

1 stop6h 38mDelta

Sat 5/243:00 pmSTX - MDW

1 stop7h 13mDelta

Deal found 4/17

$675

One-way flights from Midway to U.S. Virgin Islands
Search for one-way flight options from Midway to U.S. Virgin Islands. Find affordable one-way fares based on user searches. Data last updated April 17, 2025.

Thu 6/56:00 amMDW - STT

1 stop8h 10mDelta

Deal found 4/16

$293

Mon 4/2110:59 amMDW - STT

3 stops24h 15mMultiple Airlines

Deal found 4/16

$672

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to the U.S. Virgin Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 6/17

6:00 am-1:49 pm

1 stop6h 49m

Saint Thomas Island Cyril E King

Tue 6/24

3:00 pm-9:45 pm

1 stop7h 45m

$479

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 5/17

6:00 am-1:38 pm

1 stop6h 38m

Christiansted Henry Rohlsen

Sat 5/24

3:00 pm-9:13 pm

1 stop7h 13m

$675

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 6/5

6:00 am-3:10 pm

1 stop8h 10m

$293

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 4/21

10:59 am-12:14 pm

3 stops24h 15m

$672

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Best time to book a flight from Midway to U.S. Virgin Islands

Have a flexible travel schedule? Discover the best time to fly to U.S. Virgin Islands from Midway with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to the U.S. Virgin Islands

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing U.S. Virgin Islands

Delta

8.0

Very good

7,916 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,916 reviews

Delta

8.0

Very good

7,916 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Can I find deals for flights from Midway to U.S. Virgin Islands that include hotel bookings?
Yes. In addition to deals on Midway to U.S. Virgin Islands flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to U.S. Virgin Islands?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to U.S. Virgin Islands.
Can I find deals for business class flights from Midway to U.S. Virgin Islands?
Yes. Cheapflights offers flight deals from Midway to U.S. Virgin Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago Midway Airport to U.S. Virgin Islands?
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to U.S. Virgin Islands (average of $433). Flying from Chicago Midway Airport to U.S. Virgin Islands in June is currently the most expensive (average of $640). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Midway to U.S. Virgin Islands

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Top airline flying from Midway to U.S. Virgin Islands

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$487	Average$802	FlexibilityNo cancel fee	On-timeN/A

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$293+ Cheap flights from Midway (MDW) to the U.S. Virgin Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to U.S. Virgin Islands with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to U.S. Virgin Islands

Keep the following information in mind while searching for Midway to U.S. Virgin Islands flight deals. Data was last updated April 17, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Midway to U.S. Virgin Islands

Cheapest flights from Midway to U.S. Virgin IslandsExplore the most affordable flight options available from Midway to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

Explore the most affordable flight options available from Midway to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to the U.S. Virgin Islands that are best for you.

Best time to book a flight from Midway to U.S. Virgin Islands

Have a flexible travel schedule? Discover the best time to fly to U.S. Virgin Islands from Midway with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to the U.S. Virgin Islands

Reviews of airlines servicing U.S. Virgin Islands

Related info for your journey

Find useful and relevant information for your journey from Midway to U.S. Virgin Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

Can I find deals for flights from Midway to U.S. Virgin Islands that include hotel bookings?

How can I find direct flights from Midway to U.S. Virgin Islands?

Can I find deals for business class flights from Midway to U.S. Virgin Islands?

What is the cheapest month to book a flight from Chicago Midway Airport to U.S. Virgin Islands?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to U.S. Virgin Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Midway to U.S. Virgin Islands

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Cheapest flights from Midway to U.S. Virgin Islands
Explore the most affordable flight options available from Midway to U.S. Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.