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U.S. Virgin Islands

$288+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — STT
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$516
(Trip.com)

One-way from

$288
(Delta)

Popular in

March

Cheapest in

September

Average price

$564
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 ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
mar. 12/26:00 amMDW - STT
1 stop6h 22mDelta
mié. 12/173:32 pmSTT - MDW
1 stop8h 12mDelta
Deal found 7/29$584
This Trip.com deal was found by Cheapflights users on 7/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/184:56 pmMDW - STT
2 stops15h 48mMultiple Airlines
dom. 9/2110:49 amSTT - MDW
2 stops13h 31mMultiple Airlines
Deal found 7/31$586
This Delta deal was found by Cheapflights users on 7/30. 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.
lun. 12/296:00 amMDW - STX
1 stop6h 20mDelta
sáb. 1/33:20 pmSTX - MDW
1 stop8h 45mDelta
Deal found 7/30$1,728

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 julio 31, 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

jue. 8/21

11:03 am-11:26 am

2 stops23h 23m

Christiansted Henry Rohlsen

lun. 8/25

12:31 pm-11:27 pm

2 stops11h 56m

$516

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

jue. 9/18

4:56 pm-9:44 am

2 stops15h 48m

Saint Thomas Island Cyril E King

dom. 9/21

10:49 am-11:20 pm

2 stops13h 31m

$586

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

sáb. 8/23

6:04 am-3:10 pm

1 stop8h 06m

Saint Thomas Island Cyril E King

sáb. 8/30

3:23 pm-9:12 pm

1 stop6h 49m

$614

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

sáb. 9/27

6:00 am-2:45 pm

1 stop7h 45m

$288

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

jue. 12/25

6:00 am-2:20 pm

1 stop6h 20m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 julio 31, 2025.
Read reviews from past customers who have flown Delta from Chicago Midway Airport to the U.S. Virgin Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

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 $649). 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$487Average$689FlexibilityNo cancel feeOn-timeN/A

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