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Cheap flights from Chicago Midway Airport to the U.S. Virgin Islands from $147

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 5/10. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:51 pm - 1:31 pm
MDW
-
STT
14h 40m
1 stop
Multiple Airlines Logo
2:36 pm - 11:51 pm
STT
-
MDW
10h 15m
1 stop
$266Multiple Airlines
Mon, Mar 9 - Fri, Mar 13
Multiple Airlines Logo
11:19 am - 1:31 pm
MDW
-
STT
25h 12m
1 stop
Multiple Airlines Logo
2:36 pm - 10:19 pm
STT
-
MDW
32h 43m
2 stops
$272Multiple Airlines
Tue, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
11:19 am - 1:31 pm
MDW
-
STT
25h 12m
1 stop
Multiple Airlines Logo
2:36 pm - 6:13 pm
STT
-
MDW
28h 37m
1 stop
$273Multiple Airlines
Tue, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
9:51 pm - 1:31 pm
MDW
-
STT
14h 40m
1 stop
Multiple Airlines Logo
4:35 pm - 10:09 pm
STT
-
MDW
30h 34m
2 stops
$284Multiple Airlines
Mon, Mar 9 - Fri, Mar 13
Multiple Airlines Logo
11:19 am - 1:26 pm
MDW
-
STT
25h 07m
1 stop
Multiple Airlines Logo
4:35 pm - 1:02 pm
STT
-
MDW
21h 27m
2 stops
$291Multiple Airlines
Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
9:22 pm - 2:31 pm
MDW
-
STT
15h 09m
1 stop
Multiple Airlines Logo
3:36 pm - 9:39 pm
STT
-
MDW
32h 03m
2 stops
$292Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
8:00 am - 1:31 pm
MDW
-
STT
28h 31m
1 stop
Multiple Airlines Logo
2:36 pm - 2:21 pm
STT
-
MDW
24h 45m
1 stop
$297Multiple Airlines
Sun, Mar 8 - Sun, Mar 15
Multiple Airlines Logo
9:22 pm - 2:31 pm
MDW
-
STT
15h 09m
1 stop
Multiple Airlines Logo
3:36 pm - 2:55 pm
STT
-
MDW
25h 19m
1 stop
$299Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Delta Logo
6:00 am - 1:18 pm
MDW
-
STX
6h 18m
1 stop
Delta Logo
2:24 pm - 10:31 pm
STX
-
MDW
9h 07m
1 stop
$496Delta
Sun, Mar 22 - Wed, Mar 25
Delta Logo
6:00 am - 1:18 pm
MDW
-
STX
6h 18m
1 stop
Delta Logo
2:24 pm - 10:31 pm
STX
-
MDW
9h 07m
1 stop
$506Delta
Tue, Mar 10 - Tue, Mar 17

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
Mar 22
MDW6:00 amChicago Midway
6h 18m
1 stop
STX1:18 pmChristiansted Henry Rohlsen
Mar 25
STX2:24 pmChristiansted Henry Rohlsen
9h 07m
1 stop
MDW10:31 pmChicago Midway
$496
Delta
Mar 10
MDW6:00 amChicago Midway
6h 18m
1 stop
STX1:18 pmChristiansted Henry Rohlsen
Mar 17
STX2:24 pmChristiansted Henry Rohlsen
9h 07m
1 stop
MDW10:31 pmChicago Midway
$506
Delta
Mar 12
MDW6:00 amChicago Midway
6h 18m
1 stop
STX1:18 pmChristiansted Henry Rohlsen
Mar 17
STX2:24 pmChristiansted Henry Rohlsen
9h 07m
1 stop
MDW10:31 pmChicago Midway
$521

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
Mar 4
MDW5:00 amChicago Midway
7h 55m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Mar 11
STT1:50 pmSaint Thomas Island Cyril E King
9h 05m
2 stops
MDW9:55 pmChicago Midway
$468
Southwest
Mar 4
MDW5:00 amChicago Midway
7h 55m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Mar 11
STT1:50 pmSaint Thomas Island Cyril E King
10h 00m
2 stops
MDW10:50 pmChicago Midway
$484
Southwest
Mar 3
MDW5:00 amChicago Midway
7h 55m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Mar 10
STT1:50 pmSaint Thomas Island Cyril E King
9h 50m
1 stop
MDW10:40 pmChicago Midway
$499

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 February 11, 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

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 3/9

9:51 pm-1:31 pm

1 stop14h 40m

Saint Thomas Island Cyril E King

Fri 3/13

2:36 pm-11:51 pm

1 stop10h 15m

$266

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 3/10

11:19 am-1:31 pm

1 stop25h 12m

Saint Thomas Island Cyril E King

Tue 3/17

2:36 pm-10:19 pm

2 stops32h 43m

$272

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 3/10

11:19 am-1:31 pm

1 stop25h 12m

Saint Thomas Island Cyril E King

Tue 3/17

2:36 pm-6:13 pm

1 stop28h 37m

$273

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 3/9

9:51 pm-1:31 pm

1 stop14h 40m

Saint Thomas Island Cyril E King

Fri 3/13

4:35 pm-10:09 pm

2 stops30h 34m

$284

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 3/11

11:19 am-1:26 pm

1 stop25h 07m

Saint Thomas Island Cyril E King

Wed 3/18

4:35 pm-1:02 pm

2 stops21h 27m

$291

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 2/23

9:22 pm-2:31 pm

1 stop15h 09m

Saint Thomas Island Cyril E King

Fri 2/27

3:36 pm-9:39 pm

2 stops32h 03m

$292

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 3/8

8:00 am-1:31 pm

1 stop28h 31m

Saint Thomas Island Cyril E King

Sun 3/15

2:36 pm-2:21 pm

1 stop24h 45m

$297

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 2/23

9:22 pm-2:31 pm

1 stop15h 09m

Saint Thomas Island Cyril E King

Fri 2/27

3:36 pm-2:55 pm

1 stop25h 19m

$299

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sun 3/22

6:00 am-1:18 pm

1 stop6h 18m

Christiansted Henry Rohlsen

Wed 3/25

2:24 pm-10:31 pm

1 stop9h 07m

$496

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Tue 3/10

6:00 am-1:18 pm

1 stop6h 18m

Christiansted Henry Rohlsen

Tue 3/17

2:24 pm-10:31 pm

1 stop9h 07m

$506

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 18m

Direct flights

None
The fastest flight from Chicago Midway Airport to U.S. Virgin Islands takes 6h 18m
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

  • 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.

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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 $120