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Cheap flights from Chicago Midway Airport to the U.S. Virgin Islands from $202

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to the U.S. Virgin Islands departing on 10/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to the U.S. Virgin Islands

Cheap round-trip flights

Delta Logo
6:00 am - 1:39 pmMDW-STT
6h 39m1 stop
Delta Logo
2:49 pm - 10:14 pmSTT-MDW
8h 25m1 stop
$509Delta
Find Deal
Tue, Oct 7 - Thu, Oct 30
Delta Logo
6:00 am - 1:39 pmMDW-STT
6h 39m1 stop
Delta Logo
2:49 pm - 10:14 pmSTT-MDW
8h 25m1 stop
$539Delta
Find Deal
Mon, Oct 6 - Thu, Oct 30
Delta Logo
6:00 am - 2:24 pmMDW-STX
6h 24m1 stop
Delta Logo
3:19 pm - 9:46 pmSTX-MDW
8h 27m1 stop
$545Delta
Find Deal
Sat, Jan 24 - Sat, Jan 31
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
1:55 pm - 9:46 pmSTT-MDW
9h 51m1 stop
$569Delta
Find Deal
Sat, Jan 10 - Fri, Jan 16
Delta Logo
6:00 am - 2:22 pmMDW-STT
6h 22m1 stop
Delta Logo
3:32 pm - 9:44 pmSTT-MDW
8h 12m1 stop
$584Delta
Find Deal
Tue, Nov 18 - Thu, Nov 27
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$599Delta
Find Deal
Sun, Jan 18 - Sun, Jan 25
Delta Logo
6:00 am - 1:33 pmMDW-STT
6h 33m1 stop
Delta Logo
2:43 pm - 9:36 pmSTT-MDW
7h 53m1 stop
$609Delta
Find Deal
Sat, Sep 20 - Fri, Sep 26
Delta Logo
6:00 am - 1:39 pmMDW-STT
6h 39m1 stop
Delta Logo
2:49 pm - 10:14 pmSTT-MDW
8h 25m1 stop
$614Delta
Find Deal
Tue, Oct 7 - Thu, Oct 23
Southwest Logo
5:30 am - 2:55 pmMDW-STT
7h 25m1 stop
Southwest Logo
3:55 pm - 9:00 pmSTT-MDW
7h 05m1 stop
$819Southwest
Find Deal
Fri, Feb 6 - Tue, Feb 10
Southwest Logo
5:30 am - 2:55 pmMDW-STT
7h 25m1 stop
Southwest Logo
3:55 pm - 9:00 pmSTT-MDW
7h 05m1 stop
$1,029Southwest
Find Deal
Fri, Feb 6 - Mon, Feb 9

Delta flights from Chicago Midway Airport to U.S. Virgin Islands

Our best Delta deals on Chicago Midway Airport to U.S. Virgin Islands flight tickets
Delta
Oct 7
MDW6:00 amChicago Midway
6h 39m
1 stop
STT1:39 pmSaint Thomas Island Cyril E King
Oct 30
STT2:49 pmSaint Thomas Island Cyril E King
8h 25m
1 stop
MDW10:14 pmChicago Midway
$509
Find similar
Delta
Oct 6
MDW6:00 amChicago Midway
6h 39m
1 stop
STT1:39 pmSaint Thomas Island Cyril E King
Oct 30
STT2:49 pmSaint Thomas Island Cyril E King
8h 25m
1 stop
MDW10:14 pmChicago Midway
$539
Find similar
Delta
Jan 24
MDW6:00 amChicago Midway
6h 24m
1 stop
STX2:24 pmChristiansted Henry Rohlsen
Jan 31
STX3:19 pmChristiansted Henry Rohlsen
8h 27m
1 stop
MDW9:46 pmChicago Midway
$545
Find similar

Southwest flights from Chicago Midway Airport to U.S. Virgin Islands

Our best Southwest deals on Chicago Midway Airport to U.S. Virgin Islands flight tickets
Southwest
Feb 6
MDW5:30 amChicago Midway
7h 25m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Feb 10
STT3:55 pmSaint Thomas Island Cyril E King
7h 05m
1 stop
MDW9:00 pmChicago Midway
$819
Find similar
Southwest
Feb 6
MDW5:30 amChicago Midway
7h 25m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Feb 9
STT3:55 pmSaint Thomas Island Cyril E King
7h 05m
1 stop
MDW9:00 pmChicago Midway
$1,029
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 13, 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

Fly to

Route

Depart

Return

Price

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 10/7

6:00 am-1:39 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Thu 10/30

2:49 pm-10:14 pm

1 stop8h 25m

$509

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 10/6

6:00 am-1:39 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Thu 10/30

2:49 pm-10:14 pm

1 stop8h 25m

$539

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 1/24

6:00 am-2:24 pm

1 stop6h 24m

Christiansted Henry Rohlsen

Sat 1/31

3:19 pm-9:46 pm

1 stop8h 27m

$545

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 1/10

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Fri 1/16

1:55 pm-9:46 pm

1 stop9h 51m

$569

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 11/18

6:00 am-2:22 pm

1 stop6h 22m

Saint Thomas Island Cyril E King

Thu 11/27

3:32 pm-9:44 pm

1 stop8h 12m

$584

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 1/18

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Sun 1/25

4:00 pm-9:46 pm

1 stop7h 46m

$599

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 9/20

6:00 am-1:33 pm

1 stop6h 33m

Saint Thomas Island Cyril E King

Fri 9/26

2:43 pm-9:36 pm

1 stop7h 53m

$609

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 10/7

6:00 am-1:39 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Thu 10/23

2:49 pm-10:14 pm

1 stop8h 25m

$614

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 2/6

5:30 am-2:55 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

Tue 2/10

3:55 pm-9:00 pm

1 stop7h 05m

$819

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 2/6

5:30 am-2:55 pm

1 stop7h 25m

Saint Thomas Island Cyril E King

Mon 2/9

3:55 pm-9:00 pm

1 stop7h 05m

$1,029

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to the U.S. Virgin Islands from

How to get the cheapest flight ticket from Chicago Midway Airport to U.S. Virgin Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to U.S. Virgin Islands?

According to our data, Wednesday is the cheapest day to fly to U.S. Virgin Islands from Chicago Midway Airport. The lowest ticket price found for a Wednesday departure recently was $617. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,370.

Cheap Chicago Midway Airport to U.S. Virgin Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to U.S. Virgin Islands

Best Price Found

$202

Fastest flight time

6h 20m

Direct flights

None

Airports in U.S. Virgin Islands

2 airports
The best one-way flight to U.S. Virgin Islands from Chicago Midway Airport in the past 72 hours is $202. The best round-trip flight deal from Chicago Midway Airport to U.S. Virgin Islands found on momondo in the last 72 hours is $509.
The fastest flight from Chicago Midway Airport to U.S. Virgin Islands takes 6h 20m
There are no direct flights from Chicago Midway Airport to U.S. Virgin Islands. Popular non-direct routes for this connection are Chicago Midway Airport - Christiansted Henry Rohlsen Airport and Chicago Midway Airport - Saint Thomas Island Cyril E King Airport.
There are 2 airports near U.S. Virgin Islands: Saint Thomas Island Cyril E King (STT), Christiansted Henry Rohlsen (STX)
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to U.S. Virgin Islands?

    Prices for flights from Chicago Midway Airport to U.S. Virgin Islands are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to U.S. Virgin Islands?

  • How old do you have to be to fly from Chicago Midway Airport to U.S. Virgin Islands?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to U.S. Virgin Islands.

  • What documentation or ID do you need to fly to U.S. Virgin Islands?

    The necessary travel and health documents for your U.S. Virgin Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago Midway Airport to U.S. Virgin Islands

Compare and see reviews for airlines that fly from Chicago Midway Airport to U.S. Virgin Islands with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $487Free CancellationRating
8.0
7,979 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to U.S. Virgin Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to U.S. Virgin Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to U.S. Virgin Islands with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to U.S. Virgin Islands flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to U.S. Virgin Islands?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to U.S. Virgin Islands from Chicago.

I’m not ready to book a flight from Chicago to U.S. Virgin Islands right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to U.S. Virgin Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the U.S. Virgin Islands

Popular cities in the U.S. Virgin Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to Saint Thomas Islandfrom $174