Skip to main content
Beginning of main content

SXM (Philipsburg) to MDW (Chicago) Flights $525.57

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

Cheap SXM to MDW Flights

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



Interesting Facts About Flights from Philipsburg to Chicago (SXM to MDW)

Question : What price range should you expect when booking from Sint Maarten (SXM) to Chicago (MDW)?
Answer : Flight prices fluctuate less than most routes from Sint Maarten for SXM to MDW. They range from $526 to $641. Prices tend to be lower the further out you book.

Question : Will you do what it takes to get the absolute cheapest flight?
Answer : The cheapest day to fly in August is Thursday. Being flexible with your travel days garners even more savings during booking.

Question : Do travelers from Sint Maarten typically stay in Chicago for very long?
Answer : The average time spent in Chicago by passengers from Sint Maarten is about one week.

Question : What is the cheapest round-trip ticket you can get to Chicago?
Answer : Delta Air Lines is your best bet for finding that coveted low fare. They're offering fares as low as $526, while prices for other flights are as high as $641.

Question : Should you take that vacation to Chicago in the next 30 days?
Answer : As of Jul 24th, the best day for deals to Chicago (MDW) is Aug 24th. It costs $526, which is 7% below the average price to book the same route.