Cheap Flights from Chicago Midway to Cyril E. King from $623

Compare Chicago Midway to Cyril E. King flight deals

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Flight deals from Chicago Midway to Cyril E. King

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to Cyril E. King? Find the lowest prices on one-way and return tickets right here.

Saint Thomas.$623 per passenger.Departing Sat, 7 Mar, returning Sat, 14 Mar.Return flight with Frontier Airlines and Spirit Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 7 Mar, arriving in Cyril E. King.Inbound indirect flight with Spirit Airlines, departs from Cyril E. King on Sat, 14 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $623, select.

Saint Thomas.$775 per passenger.Departing Tue, 21 Apr, returning Tue, 28 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 21 Apr, arriving in Cyril E. King.Inbound indirect flight with Southwest Airlines, departs from Cyril E. King on Tue, 28 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $775, select.

Saint Thomas.$861 per passenger.Departing Fri, 15 May, returning Mon, 18 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 15 May, arriving in Cyril E. King.Inbound indirect flight with Southwest Airlines, departs from Cyril E. King on Mon, 18 May, arriving in Chicago Midway.Price includes taxes and charges.From $861, select.

Saint Thomas.$884 per passenger.Departing Wed, 29 Apr, returning Wed, 6 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 29 Apr, arriving in Cyril E. King.Inbound indirect flight with Southwest Airlines, departs from Cyril E. King on Wed, 6 May, arriving in Chicago Midway.Price includes taxes and charges.From $884, select.

Saint Thomas.$918 per passenger.Departing Sun, 1 Mar, returning Fri, 1 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 1 Mar, arriving in Cyril E. King.Inbound indirect flight with Southwest Airlines, departs from Cyril E. King on Fri, 1 May, arriving in Chicago Midway.Price includes taxes and charges.From $918, select.

Saint Thomas.$1,025 per passenger.Departing Sat, 15 Aug, returning Sat, 22 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 15 Aug, arriving in Cyril E. King.Inbound indirect flight with Delta, departs from Cyril E. King on Sat, 22 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $1,025, select.

Saint Thomas.$1,059 per passenger.Departing Sun, 14 Jun, returning Wed, 17 Jun.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 14 Jun, arriving in Cyril E. King.Inbound indirect flight with Southwest Airlines, departs from Cyril E. King on Wed, 17 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $1,059, select.

Saint Thomas.$1,061 per passenger.Departing Sat, 28 Feb, returning Wed, 4 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 28 Feb, arriving in Cyril E. King.Inbound indirect flight with Southwest Airlines, departs from Cyril E. King on Wed, 4 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $1,061, select.

Find the cheapest month to fly from Chicago Midway to Cyril E. King

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Cyril E. King flights are currently cheapest in March.

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Chicago to Saint Thomas: Flight information

The things to know before you go.

Cheapest flight found	$623
Cheapest month to fly	March

Finding cheap flights from Chicago Midway to Cyril E. King: Frequently asked questions

How much are return flights from Chicago Midway to Cyril E. King?

The best price we found for a return flight from Chicago Midway to Cyril E. King is $623. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Chicago Midway to Cyril E. King?

Currently, there are no airlines that fly direct from Chicago Midway to Cyril E. King. But we found flights with one or more stops from $623.

How many flights are there a week from Chicago Midway to Cyril E. King?

As of February 2026, there are no flights flying from Chicago Midway to Cyril E. King.

When is the cheapest time to fly from Chicago Midway to Cyril E. King?

The cheapest month to fly from Chicago Midway to Cyril E. King is usually March.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Cyril E. King Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Cyril E. King Airport on Saturday, 7 March 2026.

Can I get a direct flight from Chicago Midway Airport to Cyril E. King Airport?

No airlines currently offer direct flights between Chicago Midway Airport and Cyril E. King Airport. Most routes have one or more stops.

How can I find the best flight deal to Cyril E. King?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Cyril E. King but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Saint Thomas?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Saint Thomas is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Chicago Midway Airport to Cyril E. King with?

Currently, Frontier Airlines offers the cheapest flight tickets to Cyril E. King.

Flying from Chicago Midway International Airport (MDW) to Cyril E. King Airport (STT): what you need to know

Give yourself plenty of time to make your MDW to STT flight. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.
If you're heading away during a bank holiday or other peak periods, give yourself extra time. A good general rule is two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.
We make it a cinch to book a flight with a stopover. To see all your options for tickets from Chicago Midway International Airport to Cyril E. King Airport, uncheck 'Direct flights only.' Then, pick a flight offering a stop long enough to explore your chosen city. Worthwhile stopovers between MDW and STT include:
- Luis Munoz Marin International Airport
- Hartsfield-Jackson Atlanta International Airport
- Miami International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Cyril E. King Airport (STT)

$272 is the lowest price for a one-way Chicago Midway International Airport to Cyril E. King Airport flight. A return flight starts from $623. These fares may change based on availability and demand.
It's often best to book as early as possible if you want to get cheap tickets from MDW to STT. That's because flight prices are based on demand, which tends to rise closer to departure.
The 'Whole month' tool shows you the cheapest flights from Chicago Midway International Airport to Cyril E. King Airport across the month. It's an easy way to find a bargain if your trip dates aren't set in stone.
Snapping up cheap flights from MDW to STT is a breeze with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch when a new discounted fare appears.
Pick your preferred arrival and departure times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to find the best deals on flights from Chicago Midway International Airport to Cyril E. King Airport.

Handy information about Chicago Midway International Airport (MDW)

You'll find MDW at 5700 South Cicero.
77.88% of flights that leave from Chicago Midway International Airport reach their destination on schedule.
Chicago Midway International Airport is around 19 kilometres from central Chicago. If you're driving, ride-sharing or catching a cab from the centre, it'll take 20 minutes or so to get there, depending on the traffic.
Expect a journey time of roughly 45 minutes when using public transport.
Booked an early flight from Chicago Midway International Airport to Cyril E. King Airport? Avoid the last-minute rush to the terminal (and sneak in some extra precious sleep) by choosing one of these hotels close to MDW: