Skip to main content
Beginning of main content

Cheap Flights from Chicago to Fort Myers $200.73

Search over 282,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia’s Price Pledge
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Chicago to Fort Myers (MDW to RSW)

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

Interesting Facts About Flights from Chicago to Fort Myers (MDW to RSW)

Question : How long are most people's visits to Fort Myers when they fly in from Chicago?
Answer : The average time spent in Fort Myers by travelers flying from MDW is nine days.

Question : Which airline is struggling to get to Fort Myers on time?
Answer : NetJets Aviation flights from MDW to RSW are late 50% of the time. If you're on NetJets Aviation, be sure to sign up for the delay notifications to stay up to date with your flight's status.

Question : Is Chicago Midway International Airport (MDW) the cheapest airport for getting to Southwest Florida International Airport (RSW)?
Answer : Luckily for you, there is another airport nearby. O'Hare International Airport (ORD) is 16 miles away, and over the upcoming months, flights are 52% cheaper than those from Chicago Midway International Airport.

Question : Which airline is giving the best deals for round-trip flights from Chicago Midway International Airport (MDW) to Southwest Florida International Airport (RSW)?
Answer : Delta Air Lines is your best bet for finding that coveted low fare.

Question : How long does it take to get from MDW to RSW?
Answer : The shortest direct flight is 2 hours and 40 minutes via Southwest Airlines. If you catch the 7:30 AM CST departure, you'll arrive at 11:10 AM EST (remember, there is a one-hour time change to make sure you're on time for all your appointments).