What is the most punctual flight time for Chicago to the U.S. Virgin Islands flights?

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How often are flights from Chicago to the U.S. Virgin Islands delayed?

Historically, on average around 83% of flights between Chicago and U.S. Virgin Islands have experienced a delay on any given week. The average delay length over the past 12 months has been 177 minutes.

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.

$196 Cheap Flights from Chicago Midway Airport to U.S. Virgin Islands in 2026

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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:00 am - 1:50 pm

MDW

STT

7h 50m

1 stop

2:50 pm - 12:20 am

STT

MDW

10h 30m

1 stop

$474Southwest

Fri, Sep 25 - Thu, Oct 1

5:00 am - 1:50 pm

MDW

STT

7h 50m

1 stop

2:35 pm - 9:30 pm

STT

MDW

7h 55m

1 stop

$528Southwest

Mon, Sep 7 - Thu, Sep 10

5:00 am - 1:50 pm

MDW

STT

7h 50m

1 stop

2:35 pm - 10:40 pm

STT

MDW

9h 05m

1 stop

$550Southwest

Mon, Aug 31 - Fri, Sep 4

4:05 pm - 1:25 pm

MDW

STT

20h 20m

2 stops

2:05 pm - 8:55 pm

STT

MDW

7h 50m

1 stop

$577Southwest

Sat, Aug 29 - Sat, Sep 5

5:10 am - 1:25 pm

MDW

STT

7h 15m

1 stop

2:10 pm - 9:20 pm

STT

MDW

8h 10m

1 stop

$580Southwest

Sun, Aug 23 - Sun, Aug 30

6:00 am - 2:39 pm

MDW

STT

6h 39m

1 stop

3:50 pm - 10:10 pm

STT

MDW

8h 20m

1 stop

$590Delta

Tue, Nov 3 - Wed, Nov 11

7:55 pm - 1:20 pm

MDW

STT

16h 25m

2 stops

2:35 pm - 10:40 pm

STT

MDW

9h 05m

1 stop

$600Southwest

Fri, Aug 28 - Fri, Sep 4

5:00 am - 2:00 pm

MDW

STT

8h 00m

1 stop

2:50 pm - 1:05 am

STT

MDW

11h 15m

2 stops

$605Southwest

Mon, Oct 19 - Mon, Oct 26

6:00 pm - 1:25 pm

MDW

STT

18h 25m

2 stops

2:05 pm - 8:55 pm

STT

MDW

7h 50m

1 stop

$607Southwest

Sat, Aug 29 - Sat, Sep 5

6:11 am - 2:03 pm

MDW

STX

6h 52m

1 stop

3:08 pm - 10:36 pm

STX

MDW

8h 28m

1 stop

$726Delta

Sat, Aug 15 - Sat, Aug 22

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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 25

MDW5:00 amChicago Midway

7h 50m

1 stop

STT1:50 pmSaint Thomas Island Cyril E King

Oct 1

STT2:50 pmSaint Thomas Island Cyril E King

10h 30m

1 stop

MDW12:20 amChicago Midway

$474

Southwest

Sep 7

MDW5:00 amChicago Midway

7h 50m

1 stop

STT1:50 pmSaint Thomas Island Cyril E King

Sep 10

STT2:35 pmSaint Thomas Island Cyril E King

7h 55m

1 stop

MDW9:30 pmChicago Midway

$528

Southwest

Aug 31

MDW5:00 amChicago Midway

7h 50m

1 stop

STT1:50 pmSaint Thomas Island Cyril E King

Sep 4

STT2:35 pmSaint Thomas Island Cyril E King

9h 05m

1 stop

MDW10:40 pmChicago Midway

$550

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 21

MDW6:05 amChicago Midway

6h 37m

1 stop

STT1:42 pmSaint Thomas Island Cyril E King

Sep 28

STT2:52 pmSaint Thomas Island Cyril E King

8h 53m

1 stop

MDW10:45 pmChicago Midway

$640

Delta

Sep 1

MDW6:05 amChicago Midway

6h 29m

1 stop

STT1:34 pmSaint Thomas Island Cyril E King

Sep 6

STT2:49 pmSaint Thomas Island Cyril E King

8h 47m

1 stop

MDW10:36 pmChicago Midway

$645

Delta

Sep 17

MDW6:05 amChicago Midway

6h 37m

1 stop

STT1:42 pmSaint Thomas Island Cyril E King

Sep 22

STT2:52 pmSaint Thomas Island Cyril E King

8h 53m

1 stop

MDW10:45 pmChicago Midway

$650

momondo Fare Finder

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

Fri 9/25

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Thu 10/1

2:50 pm-12:20 am

1 stop10h 30m

$474

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 9/7

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Thu 9/10

2:35 pm-9:30 pm

1 stop7h 55m

$528

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 8/31

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Fri 9/4

2:35 pm-10:40 pm

1 stop9h 05m

$550

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 8/29

4:05 pm-1:25 pm

2 stops20h 20m

Saint Thomas Island Cyril E King

Sat 9/5

2:05 pm-8:55 pm

1 stop7h 50m

$577

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 8/23

5:10 am-1:25 pm

1 stop7h 15m

Saint Thomas Island Cyril E King

Sun 8/30

2:10 pm-9:20 pm

1 stop8h 10m

$580

Quickest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 11/3

6:00 am-2:39 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Wed 11/11

3:50 pm-10:10 pm

1 stop8h 20m

$590

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 8/28

7:55 pm-1:20 pm

2 stops16h 25m

Saint Thomas Island Cyril E King

Fri 9/4

2:35 pm-10:40 pm

1 stop9h 05m

$600

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 10/19

5:00 am-2:00 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

Mon 10/26

2:50 pm-1:05 am

2 stops11h 15m

$605

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 8/29

6:00 pm-1:25 pm

2 stops18h 25m

Saint Thomas Island Cyril E King

Sat 9/5

2:05 pm-8:55 pm

1 stop7h 50m

$607

ChicagoChristiansted

MDW - STX

MDWSTX

Chicago Midway

Sat 8/15

6:11 am-2:03 pm

1 stop6h 52m

Christiansted Henry Rohlsen

Sat 8/22

3:08 pm-10:36 pm

1 stop8h 28m

$726

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Airlines

Delays

What is the cheapest airline that flies from Chicago Midway to U.S. Virgin Islands?

Southwest and Delta are the most popular carriers 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.

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Popular cities in the U.S. Virgin Islands

Flights to Saint Thomas Islandfrom $270

Cheap flights from Chicago Midway Airport to the U.S. Virgin Islands from $196

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

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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

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

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to the U.S. Virgin Islands that are best for you.

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

What is the cheapest airline that flies from Chicago Midway to U.S. Virgin Islands?

How often are flights from Chicago to the U.S. Virgin Islands delayed?

What is the most punctual flight time for Chicago to the U.S. Virgin Islands flights?

What day of the week experiences the fewest flight delays on this route?

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

Fastest flight time

Direct flights

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

Why use momondo?

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

U.S. Virgin Islands flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to the U.S. Virgin Islands

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to the U.S. Virgin Islands

List of cabin classes available on flights landing in the U.S. Virgin Islands. Availability may vary depending on flight origin and airline.

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According to popular flight searches on momondo this year