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U.S. Virgin Islands

$328+ 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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — STT
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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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 June 12, 2025.

Round-trip from

$380
(Mytrip)

One-way from

$328
(Delta)

Popular in

March

Cheapest in

September

Average price

$759
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. 7% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1810:31 amMDW - STX
2 stops27h 58mMultiple Airlines
Sun 7/205:09 pmSTX - MDW
2 stops21h 55mMultiple Airlines
Deal found 6/11$380
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1810:31 amMDW - STT
2 stops22h 17mMultiple Airlines
Sun 7/204:05 pmSTT - MDW
2 stops22h 59mMultiple Airlines
Deal found 6/11$389
This FlightHub deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:20 amMDW - STT
2 stops9h 09mFrontier
Fri 8/15:14 pmSTT - MDW
2 stops28h 08mFrontier
Deal found 6/9$450
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 amMDW - STT
1 stop6h 32mDelta
Wed 11/123:32 pmSTT - MDW
1 stop8h 12mDelta
Deal found 6/9$509
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/266:00 amMDW - STX
1 stop6h 30mDelta
Sat 8/22:30 pmSTX - MDW
1 stop8h 12mDelta
Deal found 6/11$690

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to U.S. Virgin Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
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

Midway

Fly to

U.S. Virgin Islands

Route

Depart

Return

Price

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Fri 7/18

10:31 am-3:29 pm

2 stops27h 58m

Christiansted Henry Rohlsen

Sun 7/20

5:09 pm-2:04 pm

2 stops21h 55m

$380

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 7/18

10:31 am-9:48 am

2 stops22h 17m

Saint Thomas Island Cyril E King

Sun 7/20

4:05 pm-2:04 pm

2 stops22h 59m

$389

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 7/25

6:20 am-4:29 pm

2 stops9h 09m

Saint Thomas Island Cyril E King

Fri 8/1

5:14 pm-8:22 pm

2 stops28h 08m

$450

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 11/3

6:00 am-2:32 pm

1 stop6h 32m

Saint Thomas Island Cyril E King

Wed 11/12

3:32 pm-9:44 pm

1 stop8h 12m

$509

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 7/26

6:00 am-1:30 pm

1 stop6h 30m

Christiansted Henry Rohlsen

Sat 8/2

2:30 pm-9:42 pm

1 stop8h 12m

$690

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 7/26

6:00 am-3:00 pm

1 stop8h 00m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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

Get insights into the airlines that provide service to U.S. Virgin Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to U.S. Virgin Islands. Reviews last updated June 12, 2025.
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
6.0
Okay
3,295 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    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 $650). 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

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Alternative routes for Midway to U.S. Virgin Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to U.S. Virgin Islands

Discover the top airline that operate flights from Midway to U.S. Virgin Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$487Average$734FlexibilityNo cancel feeOn-timeN/A

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