Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to the U.S. Virgin Islands from $153

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 11/24. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
7:47 pm - 11:56 amMDW-STT
38h 09m2 stops
Multiple Airlines Logo
3:54 pm - 9:58 pmSTT-MDW
8h 04m1 stop
$372Multiple Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$380Delta
Find Deal
Tue, Jan 6 - Tue, Jan 13
Delta Logo
6:00 am - 4:25 pmMDW-STT
8h 25m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$410Delta
Find Deal
Thu, Jan 1 - Mon, Jan 12
Multiple Airlines Logo
2:16 pm - 2:28 pmMDW-STT
22h 12m1 stop
Multiple Airlines Logo
4:06 pm - 9:13 amSTT-MDW
19h 07m1 stop
$431Multiple Airlines
Find Deal
Sat, Jan 3 - Sat, Jan 10
Delta Logo
6:00 am - 2:55 pmMDW-STT
6h 55m1 stop
Delta Logo
3:00 pm - 9:46 pmSTT-MDW
8h 46m1 stop
$439Delta
Find Deal
Tue, Jan 6 - Fri, Jan 16
Multiple Airlines Logo
2:16 pm - 2:28 pmMDW-STT
22h 12m1 stop
Multiple Airlines Logo
1:33 pm - 11:25 pmSTT-MDW
11h 52m2 stops
$446Multiple Airlines
Find Deal
Sat, Jan 3 - Sat, Jan 10
Multiple Airlines Logo
3:10 pm - 2:28 pmMDW-STT
21h 18m1 stop
Multiple Airlines Logo
1:33 pm - 11:25 pmSTT-MDW
11h 52m2 stops
$449Multiple Airlines
Find Deal
Thu, Jan 1 - Mon, Jan 12
Multiple Airlines Logo
6:37 pm - 2:49 pmMDW-STT
18h 12m1 stop
Multiple Airlines Logo
2:22 pm - 1:01 pmSTT-MDW
48h 39m2 stops
$517Multiple Airlines
Find Deal
Sun, Dec 7 - Sun, Dec 14
Multiple Airlines Logo
6:02 pm - 2:30 pmMDW-STT
18h 28m1 stop
Multiple Airlines Logo
3:25 pm - 1:01 pmSTT-MDW
23h 36m2 stops
$550Multiple Airlines
Find Deal
Sat, Nov 29 - Wed, Dec 3
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$569Delta
Find Deal
Tue, Jan 6 - Fri, Jan 16

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
Jan 6
MDW6:00 amChicago Midway
7h 54m
1 stop
STT3:54 pmSaint Thomas Island Cyril E King
Jan 13
STT4:00 pmSaint Thomas Island Cyril E King
7h 46m
1 stop
MDW9:46 pmChicago Midway
$380
Find similar
Delta
Jan 1
MDW6:00 amChicago Midway
8h 25m
1 stop
STT4:25 pmSaint Thomas Island Cyril E King
Jan 12
STT4:00 pmSaint Thomas Island Cyril E King
7h 46m
1 stop
MDW9:46 pmChicago Midway
$410
Find similar
Delta
Jan 6
MDW6:00 amChicago Midway
6h 55m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Jan 16
STT3:00 pmSaint Thomas Island Cyril E King
8h 46m
1 stop
MDW9:46 pmChicago Midway
$439
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 October 23, 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

Thu 12/4

7:47 pm-11:56 am

2 stops38h 09m

Saint Thomas Island Cyril E King

Mon 12/8

3:54 pm-9:58 pm

1 stop8h 04m

$372

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Tue 1/13

4:00 pm-9:46 pm

1 stop7h 46m

$380

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 1/1

6:00 am-4:25 pm

1 stop8h 25m

Saint Thomas Island Cyril E King

Mon 1/12

4:00 pm-9:46 pm

1 stop7h 46m

$410

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 1/3

2:16 pm-2:28 pm

1 stop22h 12m

Saint Thomas Island Cyril E King

Sat 1/10

4:06 pm-9:13 am

1 stop19h 07m

$431

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:00 am-2:55 pm

1 stop6h 55m

Saint Thomas Island Cyril E King

Fri 1/16

3:00 pm-9:46 pm

1 stop8h 46m

$439

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 1/3

2:16 pm-2:28 pm

1 stop22h 12m

Saint Thomas Island Cyril E King

Sat 1/10

1:33 pm-11:25 pm

2 stops11h 52m

$446

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 1/1

3:10 pm-2:28 pm

1 stop21h 18m

Saint Thomas Island Cyril E King

Mon 1/12

1:33 pm-11:25 pm

2 stops11h 52m

$449

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 12/7

6:37 pm-2:49 pm

1 stop18h 12m

Saint Thomas Island Cyril E King

Sun 12/14

2:22 pm-1:01 pm

2 stops48h 39m

$517

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 11/29

6:02 pm-2:30 pm

1 stop18h 28m

Saint Thomas Island Cyril E King

Wed 12/3

3:25 pm-1:01 pm

2 stops23h 36m

$550

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Fri 1/16

4:00 pm-9:46 pm

1 stop7h 46m

$569

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

Direct flights

None
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 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 $469Free CancellationRating
7.9
7,982 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.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/22
Sat 11/29
By creating a price alert you accept our terms of use and privacy policy.

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 $185