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Cheap flights from Chicago Midway Airport to the U.S. Virgin Islands from $238

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 9/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to the U.S. Virgin Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:00 am - 1:50 pm
MDW
-
STT
7h 50m
1 stop
Southwest Logo
2:35 pm - 9:55 pm
STT
-
MDW
8h 20m
2 stops
$492Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
5:00 am - 1:50 pm
MDW
-
STT
7h 50m
1 stop
Southwest Logo
2:35 pm - 10:40 pm
STT
-
MDW
9h 05m
1 stop
$530Southwest
Mon, Sep 21 - Mon, Sep 28
Delta Logo
6:05 am - 1:44 pm
MDW
-
STT
6h 39m
1 stop
Delta Logo
2:54 pm - 10:25 pm
STT
-
MDW
8h 31m
1 stop
$580Delta
Tue, Sep 22 - Tue, Sep 29
Southwest Logo
5:00 am - 1:50 pm
MDW
-
STT
7h 50m
1 stop
Southwest Logo
2:35 pm - 10:20 pm
STT
-
MDW
8h 45m
2 stops
$582Southwest
Mon, Aug 17 - Mon, Aug 24
Delta Logo
6:05 am - 1:34 pm
MDW
-
STT
6h 29m
1 stop
Delta Logo
4:13 pm - 10:36 pm
STT
-
MDW
7h 23m
1 stop
$585Delta
Sun, Aug 16 - Sat, Aug 29
Delta Logo
6:05 am - 1:44 pm
MDW
-
STT
6h 39m
1 stop
Delta Logo
2:54 pm - 10:25 pm
STT
-
MDW
8h 31m
1 stop
$590Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
6:05 am - 1:34 pm
MDW
-
STT
6h 29m
1 stop
Delta Logo
2:49 pm - 10:36 pm
STT
-
MDW
8h 47m
1 stop
$595Delta
Sun, Aug 16 - Sat, Aug 29
Southwest Logo
8:45 pm - 1:50 pm
MDW
-
STT
16h 05m
2 stops
Southwest Logo
2:45 pm - 12:40 am
STT
-
MDW
10h 55m
1 stop
$606Southwest
Thu, Sep 24 - Thu, Oct 1
Southwest Logo
6:15 pm - 1:25 pm
MDW
-
STT
18h 10m
2 stops
Southwest Logo
2:05 pm - 8:55 pm
STT
-
MDW
7h 50m
1 stop
$624Southwest
Sat, Aug 22 - Sat, Aug 29
Delta Logo
6:05 am - 1:34 pm
MDW
-
STT
6h 29m
1 stop
Delta Logo
2:49 pm - 10:36 pm
STT
-
MDW
8h 47m
1 stop
$650Delta
Mon, Aug 10 - Thu, Aug 20

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
Sep 21
MDW5:00 amChicago Midway
7h 50m
1 stop
STT1:50 pmSaint Thomas Island Cyril E King
Sep 28
STT2:35 pmSaint Thomas Island Cyril E King
8h 20m
2 stops
MDW9:55 pmChicago Midway
$492
Southwest
Sep 21
MDW5:00 amChicago Midway
7h 50m
1 stop
STT1:50 pmSaint Thomas Island Cyril E King
Sep 28
STT2:35 pmSaint Thomas Island Cyril E King
9h 05m
1 stop
MDW10:40 pmChicago Midway
$530
Southwest
Aug 17
MDW5:00 amChicago Midway
7h 50m
1 stop
STT1:50 pmSaint Thomas Island Cyril E King
Aug 24
STT2:35 pmSaint Thomas Island Cyril E King
8h 45m
2 stops
MDW10:20 pmChicago Midway
$582

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
Sep 22
MDW6:05 amChicago Midway
6h 39m
1 stop
STT1:44 pmSaint Thomas Island Cyril E King
Sep 29
STT2:54 pmSaint Thomas Island Cyril E King
8h 31m
1 stop
MDW10:25 pmChicago Midway
$580
Delta
Aug 16
MDW6:05 amChicago Midway
6h 29m
1 stop
STT1:34 pmSaint Thomas Island Cyril E King
Aug 29
STT4:13 pmSaint Thomas Island Cyril E King
7h 23m
1 stop
MDW10:36 pmChicago Midway
$585
Delta
Sep 22
MDW6:05 amChicago Midway
6h 39m
1 stop
STT1:44 pmSaint Thomas Island Cyril E King
Sep 29
STT2:54 pmSaint Thomas Island Cyril E King
8h 31m
1 stop
MDW10:25 pmChicago Midway
$590

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 June 6, 2026.
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

Cheapest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 9/21

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Mon 9/28

2:35 pm-9:55 pm

2 stops8h 20m

$492

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 9/21

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Mon 9/28

2:35 pm-10:40 pm

1 stop9h 05m

$530

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 9/22

6:05 am-1:44 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Tue 9/29

2:54 pm-10:25 pm

1 stop8h 31m

$580

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 8/17

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Mon 8/24

2:35 pm-10:20 pm

2 stops8h 45m

$582
Quickest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 8/16

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Sat 8/29

4:13 pm-10:36 pm

1 stop7h 23m

$585

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 9/22

6:05 am-1:44 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Tue 9/29

2:54 pm-10:25 pm

1 stop8h 31m

$590

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 8/16

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Sat 8/29

2:49 pm-10:36 pm

1 stop8h 47m

$595

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 9/24

8:45 pm-1:50 pm

2 stops16h 05m

Saint Thomas Island Cyril E King

Thu 10/1

2:45 pm-12:40 am

1 stop10h 55m

$606

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 8/22

6:15 pm-1:25 pm

2 stops18h 10m

Saint Thomas Island Cyril E King

Sat 8/29

2:05 pm-8:55 pm

1 stop7h 50m

$624

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 8/10

6:05 am-1:34 pm

1 stop6h 29m

Saint Thomas Island Cyril E King

Thu 8/20

2:49 pm-10:36 pm

1 stop8h 47m

$650

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 airline that flies from Chicago Midway to U.S. Virgin Islands?

Southwest is the most popular carrier operating from Chicago Midway to U.S. Virgin Islands

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

Fastest flight time

6h 25m

Direct flights

None
The fastest flight from Chicago Midway Airport to U.S. Virgin Islands takes 6h 25m
There are no direct flights from Chicago Midway Airport to U.S. Virgin Islands. There are no popular flight routes from Chicago Midway Airport to U.S. Virgin Islands.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to the U.S. Virgin Islands

  • 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 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.

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.

An easier way to manage your U.S. Virgin Islands trip

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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 $230