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Cheap flights from Chicago Midway Airport to Saint Thomas Island from $240

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Saint Thomas Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:50 pm - 1:20 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
19h 30m2 stops Nashville Intl Baltimore/Washington
Southwest Logo
3:45 pm - 11:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 15m1 stop Baltimore/Washington
$498Southwest
Sun, Jan 31 - Sun, Feb 7
Southwest Logo
5:05 am - 2:55 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 50m1 stop Orlando
Southwest Logo
3:45 pm - 11:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 15m1 stop Baltimore/Washington
$512Southwest
Sun, Jan 31 - Sun, Feb 7
Southwest Logo
5:20 am - 2:30 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 10m1 stop Orlando
Southwest Logo
2:10 pm - 9:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 05m2 stops Orlando Nashville Intl
$522Southwest
Thu, Dec 31 - Fri, Jan 8
Southwest Logo
5:20 am - 2:30 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 10m1 stop Orlando
Southwest Logo
2:10 pm - 10:50 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
10h 40m1 stop Orlando
$522Southwest
Thu, Dec 31 - Fri, Jan 8
Southwest Logo
5:20 am - 2:30 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 10m1 stop Orlando
Southwest Logo
2:10 pm - 10:50 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
10h 40m1 stop Orlando
$522Southwest
Thu, Dec 31 - Fri, Jan 8
Southwest Logo
5:20 am - 2:30 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 10m1 stop Orlando
Southwest Logo
2:10 pm - 9:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 05m2 stops Orlando Nashville Intl
$522Southwest
Thu, Dec 31 - Fri, Jan 8
Southwest Logo
5:25 am - 2:55 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 30m1 stop Orlando
Southwest Logo
3:45 pm - 11:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 15m1 stop Baltimore/Washington
$536Southwest
Mon, Feb 1 - Sun, Feb 7
Southwest Logo
8:25 pm - 2:30 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
16h 05m2 stops Baltimore/Washington Orlando
Southwest Logo
3:45 pm - 11:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 30m1 stop Baltimore/Washington
$544Southwest
Sun, Dec 13 - Mon, Dec 21
Southwest Logo
8:25 pm - 2:30 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
16h 05m2 stops Baltimore/Washington Orlando
Southwest Logo
2:40 pm - 11:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
10h 20m2 stops Orlando Lambert-St Louis
$560Southwest
Sun, Dec 13 - Mon, Dec 21
Southwest Logo
5:05 am - 1:50 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
6h 45m1 stop Baltimore/Washington
Southwest Logo
3:45 pm - 11:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 30m1 stop Baltimore/Washington
$560Southwest
Sun, Dec 13 - Mon, Dec 21

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Delta flights from Chicago Midway Airport to Saint Thomas Island

Our best Delta deals on Chicago Midway Airport to Saint Thomas Island flight tickets
Delta
Dec 15
MDW6:00 amChicago Midway
6h 52m
1 stop
STT2:52 pmSaint Thomas Island Cyril E King
Dec 22
STT3:20 pmSaint Thomas Island Cyril E King
9h 02m
1 stop
MDW10:22 pmChicago Midway
$620
Delta
Jan 7
MDW6:00 amChicago Midway
7h 49m
1 stop
STT3:49 pmSaint Thomas Island Cyril E King
Jan 15
STT3:11 pmSaint Thomas Island Cyril E King
9h 06m
1 stop
MDW10:17 pmChicago Midway
$645
Delta
Jan 9
MDW6:00 amChicago Midway
6h 53m
1 stop
STT2:53 pmSaint Thomas Island Cyril E King
Jan 15
STT4:03 pmSaint Thomas Island Cyril E King
8h 14m
1 stop
MDW10:17 pmChicago Midway
$655

Southwest flights from Chicago Midway Airport to Saint Thomas Island

Our best Southwest deals on Chicago Midway Airport to Saint Thomas Island flight tickets
Southwest
Jan 31
MDW3:50 pmChicago Midway
19h 30m
2 stops
STT1:20 pmSaint Thomas Island Cyril E King
Feb 7
STT3:45 pmSaint Thomas Island Cyril E King
9h 15m
1 stop
MDW11:00 pmChicago Midway
$498
Southwest
Jan 31
MDW5:05 amChicago Midway
7h 50m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Feb 7
STT3:45 pmSaint Thomas Island Cyril E King
9h 15m
1 stop
MDW11:00 pmChicago Midway
$512
Southwest
Dec 31
MDW5:20 amChicago Midway
7h 10m
1 stop
STT2:30 pmSaint Thomas Island Cyril E King
Jan 8
STT2:10 pmSaint Thomas Island Cyril E King
10h 40m
1 stop
MDW10:50 pmChicago Midway
$522

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Saint Thomas Island that are best for you.

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Route

Depart

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Price

Cheapest round-trip

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 1/31

3:50 pm-1:20 pm

2 stops19h 30m

Saint Thomas Island Cyril E King

Sun 2/7

3:45 pm-11:00 pm

1 stop9h 15m

$498

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 1/31

5:05 am-2:55 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Sun 2/7

3:45 pm-11:00 pm

1 stop9h 15m

$512
Quickest round-trip

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Thu 12/31

5:20 am-2:30 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Fri 1/8

2:10 pm-9:15 pm

2 stops9h 05m

$522

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Thu 12/31

5:20 am-2:30 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Fri 1/8

2:10 pm-10:50 pm

1 stop10h 40m

$522

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Thu 12/31

5:20 am-2:30 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Fri 1/8

2:10 pm-10:50 pm

1 stop10h 40m

$522

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Thu 12/31

5:20 am-2:30 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Fri 1/8

2:10 pm-9:15 pm

2 stops9h 05m

$522

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Mon 2/1

5:25 am-2:55 pm

1 stop7h 30m

Saint Thomas Island Cyril E King

Sun 2/7

3:45 pm-11:00 pm

1 stop9h 15m

$536

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 12/13

8:25 pm-2:30 pm

2 stops16h 05m

Saint Thomas Island Cyril E King

Mon 12/21

3:45 pm-11:15 pm

1 stop9h 30m

$544

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 12/13

8:25 pm-2:30 pm

2 stops16h 05m

Saint Thomas Island Cyril E King

Mon 12/21

2:40 pm-11:00 pm

2 stops10h 20m

$560

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 12/13

5:05 am-1:50 pm

1 stop6h 45m

Saint Thomas Island Cyril E King

Mon 12/21

3:45 pm-11:15 pm

1 stop9h 30m

$560

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 Saint Thomas Island from

How to get the cheapest flight ticket from Chicago Midway Airport to Saint Thomas Island

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 Saint Thomas Island?

On average, the least expensive day to fly to Saint Thomas Island from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $571. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Saint Thomas Island for around $809.

When to book flights from Chicago Midway Airport to Saint Thomas Island

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Saint Thomas Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Saint Thomas Island (MDW to STT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Saint Thomas Island

Best Price Found

$240

Fastest flight time

6h 43m

Direct flights

None
The best one-way flight to Saint Thomas Island from Chicago Midway Airport in the past 72 hours is $240. The best round-trip flight deal from Chicago Midway Airport to Saint Thomas Island found on momondo in the last 72 hours is $498.
The fastest flight from Chicago Midway Airport to Saint Thomas Island takes 6h 43m
There are no direct flights from Chicago Midway Airport to Saint Thomas Island. There are no popular flight routes from Chicago Midway Airport to Saint Thomas Island.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Saint Thomas Island

  • How far is Chicago Midway to Saint Thomas Island Cyril E King by plane?

    A flight from Chicago Midway to Saint Thomas Island Cyril E King will travel around 2102.4 mi. A reasonable flight in good conditions will take 6h 43m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport?

    Prices for flights from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport.

  • What documentation or ID do you need to fly to Saint Thomas Island Cyril E King Airport?

    The necessary travel and health documents for your Saint Thomas Island Cyril E King Airport 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.

Traveling to a place near Saint Thomas Island?

Book flights to Saint Thomas Island if you plan to visit one of these locations
St. John

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Saint Thomas Island?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Saint Thomas Island. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Saint Thomas Island with flexible booking policies on momondo?

All flight searches from Chicago to Saint Thomas Island on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Saint Thomas Island?

momondo helps you find the best flight between Chicago and Saint Thomas Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Saint Thomas Island right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Saint Thomas Island from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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