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Cheap flights from Chicago Midway Airport to the U.S. Virgin Islands from $171

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 4/29. 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.
Multiple Airlines Logo
9:14 am - 9:54 am
MDW
-
STT
23h 40m
1 stop
Multiple Airlines Logo
10:49 am - 5:54 pm
STT
-
MDW
8h 05m
1 stop
$297Multiple Airlines
Mon, Apr 20 - Fri, Apr 24
Multiple Airlines Logo
6:00 am - 4:15 pm
MDW
-
STT
9h 15m
2 stops
Multiple Airlines Logo
10:49 am - 5:54 pm
STT
-
MDW
8h 05m
1 stop
$317Multiple Airlines
Mon, Apr 20 - Fri, Apr 24
Multiple Airlines Logo
9:14 am - 9:54 am
MDW
-
STT
23h 40m
1 stop
Multiple Airlines Logo
12:25 pm - 10:14 pm
STT
-
MDW
10h 49m
2 stops
$389Multiple Airlines
Sat, Apr 18 - Tue, Apr 21
Multiple Airlines Logo
9:14 am - 9:54 am
MDW
-
STT
23h 40m
1 stop
Multiple Airlines Logo
10:49 am - 10:19 pm
STT
-
MDW
36h 30m
2 stops
$401Multiple Airlines
Thu, Apr 16 - Sun, Apr 19
Southwest Logo
5:35 am - 1:35 pm
MDW
-
STT
7h 00m
1 stop
Southwest Logo
2:30 pm - 8:40 pm
STT
-
MDW
7h 10m
1 stop
$440Southwest
Mon, Apr 20 - Thu, Apr 23
Southwest Logo
6:00 am - 1:20 pm
MDW
-
STT
6h 20m
1 stop
Southwest Logo
2:10 pm - 9:25 pm
STT
-
MDW
8h 15m
1 stop
$452Southwest
Wed, May 6 - Tue, May 12
Southwest Logo
5:15 am - 2:25 pm
MDW
-
STT
8h 10m
1 stop
Southwest Logo
2:30 pm - 8:40 pm
STT
-
MDW
7h 10m
1 stop
$464Southwest
Sun, Apr 26 - Thu, Apr 30
Delta Logo
6:05 am - 1:57 pm
MDW
-
STX
6h 52m
1 stop
Delta Logo
3:03 pm - 10:15 pm
STX
-
MDW
8h 12m
1 stop
$606Delta
Sat, Aug 1 - Sat, Aug 8
Delta Logo
6:00 am - 1:45 pm
MDW
-
STX
6h 45m
1 stop
Delta Logo
2:55 pm - 10:28 pm
STX
-
MDW
8h 33m
1 stop
$656Delta
Sat, Apr 25 - Sat, May 2
Delta Logo
12:41 pm - 1:57 pm
MDW
-
STX
24h 16m
1 stop
Delta Logo
3:03 pm - 10:15 pm
STX
-
MDW
8h 12m
1 stop
$2,382Delta
Fri, Jul 31 - Sat, Aug 8

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
Jul 13
MDW6:05 amChicago Midway
8h 15m
1 stop
STT3:20 pmSaint Thomas Island Cyril E King
Jul 21
STT3:33 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
MDW10:15 pmChicago Midway
$580
Delta
Aug 21
MDW6:00 amChicago Midway
6h 52m
1 stop
STT1:52 pmSaint Thomas Island Cyril E King
Aug 27
STT3:02 pmSaint Thomas Island Cyril E King
7h 44m
1 stop
MDW9:46 pmChicago Midway
$585
Delta
May 2
MDW5:40 amChicago Midway
7h 11m
1 stop
STT1:51 pmSaint Thomas Island Cyril E King
May 12
STT1:16 pmSaint Thomas Island Cyril E King
8h 53m
1 stop
MDW9:09 pmChicago Midway
$605

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
Apr 20
MDW5:35 amChicago Midway
7h 00m
1 stop
STT1:35 pmSaint Thomas Island Cyril E King
Apr 23
STT2:30 pmSaint Thomas Island Cyril E King
7h 10m
1 stop
MDW8:40 pmChicago Midway
$440
Southwest
May 6
MDW6:00 amChicago Midway
6h 20m
1 stop
STT1:20 pmSaint Thomas Island Cyril E King
May 12
STT2:10 pmSaint Thomas Island Cyril E King
8h 15m
1 stop
MDW9:25 pmChicago Midway
$452
Southwest
Apr 26
MDW5:15 amChicago Midway
8h 10m
1 stop
STT2:25 pmSaint Thomas Island Cyril E King
Apr 30
STT2:30 pmSaint Thomas Island Cyril E King
7h 10m
1 stop
MDW8:40 pmChicago Midway
$464

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 April 4, 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 4/20

9:14 am-9:54 am

1 stop23h 40m

Saint Thomas Island Cyril E King

Fri 4/24

10:49 am-5:54 pm

1 stop8h 05m

$297

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 4/20

6:00 am-4:15 pm

2 stops9h 15m

Saint Thomas Island Cyril E King

Fri 4/24

10:49 am-5:54 pm

1 stop8h 05m

$317

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 4/18

9:14 am-9:54 am

1 stop23h 40m

Saint Thomas Island Cyril E King

Tue 4/21

12:25 pm-10:14 pm

2 stops10h 49m

$389

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 4/16

9:14 am-9:54 am

1 stop23h 40m

Saint Thomas Island Cyril E King

Sun 4/19

10:49 am-10:19 pm

2 stops36h 30m

$401
Quickest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 4/20

5:35 am-1:35 pm

1 stop7h 00m

Saint Thomas Island Cyril E King

Thu 4/23

2:30 pm-8:40 pm

1 stop7h 10m

$440

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 5/6

6:00 am-1:20 pm

1 stop6h 20m

Saint Thomas Island Cyril E King

Tue 5/12

2:10 pm-9:25 pm

1 stop8h 15m

$452

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 4/26

5:15 am-2:25 pm

1 stop8h 10m

Saint Thomas Island Cyril E King

Thu 4/30

2:30 pm-8:40 pm

1 stop7h 10m

$464

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 8/1

6:05 am-1:57 pm

1 stop6h 52m

Christiansted Henry Rohlsen

Sat 8/8

3:03 pm-10:15 pm

1 stop8h 12m

$606

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 4/25

6:00 am-1:45 pm

1 stop6h 45m

Christiansted Henry Rohlsen

Sat 5/2

2:55 pm-10:28 pm

1 stop8h 33m

$656

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Fri 7/31

12:41 pm-1:57 pm

1 stop24h 16m

Christiansted Henry Rohlsen

Sat 8/8

3:03 pm-10:15 pm

1 stop8h 12m

$2,382

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?

Delta 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 20m

Direct flights

None
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. 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 $183