MDW - STT

$240 Find Cheap Flights from Chicago Midway Airport to Saint Thomas Island - Compare and Save

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Everything you should know

Cheapest round-trip
$498
Typical prices: $608-$980
Southwest
Wed 1/31Wed 2/7
MDW - STT • 2 stops
Cheapest one-way
$240
Typical prices: $288-$421
Southwest
Thu 2/15
MDW - STT • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Saint Thomas Island. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
May
Cheapest • 41% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Baltimore/Washington (BWI)
Cheapest • Avg $754 (round-trip)
Orlando (MCO)
Shortest trip • 7h 21m (one-way)
Insights
Insights
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We hope you love your trip to Saint Thomas Island!
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Booking Insights
Flight Deals

Cheap Flights from Midway to Saint Thomas Island (MDW-STT)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Saint Thomas Island

Sun, Jan 31 - Sun, Feb 7
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
$498Southwest
Mon, Feb 1 - Sun, Feb 7
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
$522Southwest
Mon, Feb 1 - Sun, Feb 7
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 22 - Tue, Mar 2
Southwest Logo
8:50 pm - 2:55 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
16h 05m2 stops Baltimore/Washington Orlando
Southwest Logo
2:10 pm - 9:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
8h 50m1 stop Orlando
$538Southwest
Mon, Feb 22 - Tue, Mar 2
Southwest Logo
8:50 pm - 2:55 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
16h 05m2 stops Baltimore/Washington Orlando
Southwest Logo
2:10 pm - 9:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 05m2 stops Orlando Nashville Intl
$538Southwest
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
3:45 pm - 11:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 30m1 stop Baltimore/Washington
$544Southwest
Mon, Mar 1 - Mon, Mar 8
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
2:10 pm - 11:20 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
11h 10m1 stop Orlando
$549Southwest
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
Tue, Mar 2 - Tue, Mar 9
Southwest Logo
5:25 am - 2:55 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 30m1 stop Orlando
Southwest Logo
2:10 pm - 9:00 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
8h 50m1 stop Orlando
$560Southwest
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Saint Thomas Island flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Saint Thomas Island?

Round-trip flights from Chicago Midway Airport to Saint Thomas Island typically range from $608 to $980. The lowest price found in the past 5 days was $498, on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to Saint Thomas Island?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago Midway Airport to Saint Thomas Island. It’s 31% cheaper than the average day, while Friday is the most expensive, with prices 30% higher.

Find deals

Key details for Chicago Midway Airport to Saint Thomas Island flights

Low season

January

Cheapest flight

$240
Beat the crowds with an average 74% drop in travelers.
The most popular month to fly with an average 71% increase in travelers.
One-way flight from Chicago Midway Airport to Saint Thomas Island

When to book flights from Midway to Saint Thomas Island

Are your dates flexible? Find out the best times to travel from Midway to Saint Thomas Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Saint Thomas Island flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago Midway Airport to Saint Thomas Island?

    Only Economy Class is available on flights from Chicago Midway Airport to Saint Thomas Island.

  • How long is a flight from Chicago Midway Airport to Saint Thomas Island?

    A nonstop flight from Chicago Midway Airport to Saint Thomas Island takes 00m, covering 2,101 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Saint Thomas Island?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago Midway Airport to Saint Thomas Island flight?

    Round-trip flights from Chicago Midway Airport to Saint Thomas Island range from $608 to $980, with an average of $760 over the past 12 months. Anything below $608 counts as a good deal.

  • Have flight prices from Chicago Midway Airport to Saint Thomas Island changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $498 to $3,776. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to Saint Thomas Island looking right now?

    One-way fares from Chicago Midway Airport to Saint Thomas Island are currently lower than usual. Average one-way flight prices are about $343, which is 8% below the typical average for this route.

  • What car rental options are available at Saint Thomas Island Cyril E King Airport (STT)?

    Saint Thomas Island Cyril E King Airport (STT) hosts 5 major car rental companies, with daily rates averaging $72 for economy cars. Top options include:

    • Budget
    • Thrifty
    • Dollar
    • Alamo
    • Hertz

  • Which airports can I use when flying from Chicago Midway Airport to Saint Thomas Island?

    Flights from Chicago Midway Airport to Saint Thomas Island usually depart from Chicago Midway (MDW) and arrive at Saint Thomas Island Cyril E King (STT).

  • Which airports do connecting flights from Chicago Midway Airport to Saint Thomas Island pass through?

    One-stop flights from Chicago Midway Airport to Saint Thomas Island most commonly connect through:

    • Orlando (MCO) - 56% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 42% of one-stop connections
    • Baltimore/Washington (BWI) - 3% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Saint Thomas Island?

    Yes. Flexible dates can save you up to 47% on flights from Chicago Midway Airport to Saint Thomas Island. Wednesday is the cheapest departure day at $530 round-trip on average, while Friday is the most expensive at $993, a difference of $463.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Saint Thomas Island?

    Flying via Orlando (MCO) gives the shortest average 1-stop total travel time at 7h 21m, compared with 7h 29m via Atlanta Hartsfield-Jackson (ATL) and 7h 39m via Baltimore/Washington (BWI).

  • What is the time difference between Chicago Midway Airport and Saint Thomas Island?

    Saint Thomas Island is 2 hours ahead of Chicago Midway Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Saint Thomas Island?

    Some of the most popular sights in Saint Thomas Island are Sapphire Beach, Coki Beach and 99 Steps. These are among the most viewed places in Saint Thomas Island on KAYAK.

Your guide to booking Chicago Midway Airport to Saint Thomas Island flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Friday. On this route, Wednesday flights average $530, about $463 less than Friday fares (47% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to Saint Thomas Island trip for May. Fares historically average $452 round-trip in that month - typically $1,062 less than the most expensive month, which is March (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Saint Thomas Island Cyril E King Airport.

    • Starz Hotel
    • Sunset Gardens Guesthouse
    • Island View Guesthouse

More options for your flight from Midway to Saint Thomas Island

Complete your trip to Saint Thomas Island with a hotel stay or car rental

Car rentals in Saint Thomas Island
Hotels in Saint Thomas Island
Vacations in Saint Thomas Island