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U.S. Virgin Islands

$171+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — STT
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/305:30 pmMDW - STT
2 stops17h 25mMultiple Airlines
Fri 12/53:54 pmSTT - MDW
1 stop8h 45mMultiple Airlines
Deal found 10/30$461
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/193:10 pmMDW - STT
1 stop21h 18mMultiple Airlines
Mon 12/223:23 pmSTT - MDW
1 stop8h 35mMultiple Airlines
Deal found 10/28$492
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/218:41 pmMDW - STT
2 stops18h 08mMultiple Airlines
Fri 11/283:25 pmSTT - MDW
1 stop10h 04mMultiple Airlines
Deal found 10/29$545
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:02 pmMDW - STT
1 stop18h 28mMultiple Airlines
Fri 11/283:25 pmSTT - MDW
1 stop10h 04mMultiple Airlines
Deal found 10/29$568
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 11/166:00 amMDW - STT
1 stop6h 40mDelta
Wed 11/193:50 pmSTT - MDW
1 stop9h 50mDelta
Deal found 10/29$649
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:15 amMDW - STT
2 stops25h 16mMultiple Airlines
Mon 12/293:23 pmSTT - MDW
1 stop8h 35mMultiple Airlines
Deal found 10/29$651
This Delta deal was found by Cheapflights users on 10/28. 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 11/156:00 amMDW - STT
1 stop7h 40mDelta
Wed 11/193:50 pmSTT - MDW
1 stop9h 50mDelta
Deal found 10/28$709
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/306:00 amMDW - STX
1 stop6h 21mDelta
Wed 1/73:33 pmSTX - MDW
1 stop8h 36mDelta
Deal found 10/29$815
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/246:00 amMDW - STX
1 stop6h 21mDelta
Thu 1/83:33 pmSTX - MDW
1 stop8h 36mDelta
Deal found 10/29$1,089
This Delta deal was found by Cheapflights users on 10/29. 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.
Sat 12/276:00 amMDW - STX
1 stop6h 21mDelta
Sat 1/33:22 pmSTX - MDW
1 stop9h 00mDelta
Deal found 10/29$2,125

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(Delta)

One-way from

$171
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$554
Provider with most accurate pricing for Chicago (CHI)-Saint Thomas Island Cyril E King flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Saint Thomas Island Cyril E King flights.
Search Deals
From Chicago Midway to U.S. Virgin Islands
Search Deals
One-way flight from Chicago Midway to U.S. Virgin Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 1/22

6:00 am-3:04 pm

1 stop7h 04m

Saint Thomas Island Cyril E King

Mon 1/26

4:15 pm-10:26 pm

1 stop8h 11m

$251

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:45 am-3:04 pm

1 stop6h 19m

Saint Thomas Island Cyril E King

Fri 1/16

4:15 pm-10:09 pm

1 stop7h 54m

$345

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 1/19

6:00 am-4:10 pm

1 stop8h 10m

Saint Thomas Island Cyril E King

Fri 1/23

3:10 pm-10:26 pm

1 stop9h 16m

$345

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 1/9

6:45 am-4:10 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

Fri 1/16

4:15 pm-10:09 pm

1 stop7h 54m

$410

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 11/30

5:30 pm-12:55 pm

2 stops17h 25m

Saint Thomas Island Cyril E King

Fri 12/5

3:54 pm-10:39 pm

1 stop8h 45m

$471

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 3/4

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Wed 3/18

2:00 pm-9:46 pm

1 stop8h 46m

$539

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sun 1/25

6:00 am-2:33 pm

1 stop6h 33m

Christiansted Henry Rohlsen

Thu 1/29

3:33 pm-10:26 pm

1 stop8h 53m

$615

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Tue 2/24

6:00 am-2:24 pm

1 stop6h 24m

Christiansted Henry Rohlsen

Fri 2/27

3:19 pm-9:46 pm

1 stop8h 27m

$615

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 1/10

6:45 am-4:10 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

Fri 1/16

4:15 pm-10:09 pm

1 stop7h 54m

$635

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Thu 2/19

6:00 am-2:24 pm

1 stop6h 24m

Christiansted Henry Rohlsen

Wed 2/25

3:19 pm-9:46 pm

1 stop8h 27m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 27 results
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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 October 30, 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
7.9
Good
7,998 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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.

  • How long is the flight from Chicago Midway Airport to U.S. Virgin Islands?

    A quick flight from Chicago Midway Airport to U.S. Virgin Islands can take about 7h 04m. Delta provides one of the quickest options available for as low as $251. Airlines will cover a distance of 2101 mi.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$469Average$657FlexibilityNo cancel feeOn-timeN/A

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