Skip to main content
Beginning of main content

Cheap Flights from Chicago to Charlotte Amalie $308.33

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Best Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Chicago to Charlotte Amalie (MDW to STT)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Charlotte Amalie (MDW to STT)

Question : Should you take that vacation to Saint Thomas in the next 30 days?
Answer : January 2nd offers bookings (as of December 5th) that are 44% below the average price for this route. Saving on flight costs means you'll have more cash to spend on your trip.

Question : Do travelers from Chicago typically stay in Saint Thomas for very long?
Answer : The average time spent in Saint Thomas by passengers flying from MDW is seven days.

Question : Can you cut down on flight costs by changing the day of the week you travel to Saint Thomas?
Answer : Tuesday is your cheapest day to fly in December. Being flexible with your travel days garners you even more savings during your booking.

Question : Are prices changing frequently for this route?
Answer : Prices for this trip tend to change a lot more than others. Remember, the sooner you book, the more you're able to save.

Question : Is there another way to get to Cyril E. King Airport (STT) besides Chicago Midway International Airport (MDW)?
Answer : Luckily for you, there is another airport nearby. O'Hare International Airport (ORD) is 16 miles away, and over the next few months, flights are 30% cheaper than those from Chicago Midway International Airport.