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Not ready to book? to track prices.Southwest flights from Fort Myers to Chicago Midway Airport
Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets
Delta flights from Fort Myers to Chicago Midway Airport
Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
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Use the filters below to find and compare flights from Fort Myers to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 9/5
4:20 pm-8:35 pm
1 stop5h 15m
Chicago Midway
Sun 9/6
11:15 am-4:40 pm
1 stop4h 25m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Thu 10/1
6:40 pm-8:30 pm
Nonstop2h 50m
Chicago Midway
Sun 10/4
8:10 am-11:55 am
Nonstop2h 45m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 9/5
7:10 am-8:55 am
Nonstop2h 45m
Chicago Midway
Sun 9/6
6:25 pm-10:10 pm
Nonstop2h 45m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Thu 10/1
6:40 pm-8:30 pm
Nonstop2h 50m
Chicago Midway
Sun 10/4
7:55 am-1:05 pm
1 stop4h 10m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sun 9/20
7:20 am-9:05 am
Nonstop2h 45m
Chicago Midway
Wed 9/23
2:00 pm-10:15 pm
1 stop7h 15m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 9/5
7:20 am-11:00 am
1 stop4h 40m
Chicago Midway
Sun 9/6
6:25 pm-10:10 pm
Nonstop2h 45m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 9/5
3:15 pm-5:10 pm
Nonstop2h 55m
Chicago Midway
Mon 9/28
1:00 pm-4:45 pm
Nonstop2h 45m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 9/5
7:10 am-8:55 am
Nonstop2h 45m
Chicago Midway
Tue 9/15
8:50 am-12:40 pm
Nonstop2h 50m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 9/5
12:22 pm-4:59 pm
1 stop5h 37m
Chicago Midway
Mon 9/28
6:05 am-12:06 pm
1 stop5h 01m
Fort MyersChicago
RSW Fort Myers SW Florida Intl - MDW Chicago Midway
RSWMDW
Fort Myers SW Florida Intl
Sat 9/5
12:22 pm-4:59 pm
1 stop5h 37m
Chicago Midway
Thu 9/10
4:30 pm-12:35 am
1 stop7h 05m
See travel insights to Chicago from
How to get the cheapest flight ticket from Fort Myers to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Fort Myers and Chicago Midway Airport?
Prices are currently low for flights on this route.
Typical prices usually range from $283 to $374.The lowest price recently found on this route was $277.
What is the cheapest month to fly to Chicago Midway Airport?
The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Fort Myers, with most prices found around $255. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Fort Myers during the month September is also very affordable. Most momondo users find prices during this month for around $293.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Fort Myers. The lowest ticket price found for a Thursday departure recently was $386. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Fort Myers because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $454.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Fort Myers in the evening is the least expensive time of day to depart. momondo users have found prices as low as $318 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $504. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Fort Myers SW Florida Intl to Chicago Midway flight route?
Fly from Fort Myers SW Florida Intl to Chicago Midway for the best Fort Myers SW Florida Intl - Chicago Midway flight prices
What cabin class options are available on Fort Myers to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on Fort Myers to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Fort Myers to Chicago Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Fort Myers to Chicago Midway Airport.
How many flights depart from Fort Myers to Chicago Midway Airport on average per day?
As of August 2026, 1 flights take off from Fort Myers and land in Chicago Midway Airport each day. The most common flight departure time for this route is 6:00AM, with 63% of daily flights taking off at noon.
How many flights depart from Fort Myers to Chicago Midway Airport on average per week?
As of August 2026, 12 flights take off from Fort Myers and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.
When to book flights from Fort Myers to Chicago Midway Airport
Cheap Fort Myers to Chicago Midway Airport (RSW to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Fort Myers to Chicago Midway Airport
Frequently asked questions about flying from Fort Myers to Chicago Midway Airport
How far is Fort Myers SW Florida Intl to Chicago Midway by plane?
A flight from Fort Myers SW Florida Intl to Chicago Midway will travel around 1097.4 mi. Typically, this will take 2h 45m by plane in normal conditions.
When did momondo last update prices for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport?
Prices for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport?
There is 1 operator available for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport as of August 2026.
How old do you have to be to fly from Fort Myers SW Florida Intl Airport to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Fort Myers SW Florida Intl Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Fort Myers to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Fort Myers to Chicago Midway Airport is Boeing 737 MAX 8, representing 23.68% of all bookings. The subsequent popular models are Boeing 737-800 at 14.31%, Airbus A321neo at 12.78%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 12.44%.
What is the most popular airline from Fort Myers to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Fort Myers to Chicago Midway Airport is Southwest (100% of total bookings).
Best airlines flying from Fort Myers to Chicago Midway Airport
Compare and see reviews for airlines that fly from Fort Myers to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $188 | Free Cancellation | Rating 8.0 4,218 reviews |
Southwest Flights From Fort Myers to Chicago Midway Airport
Southwest flight deals from Fort Myers to Chicago Midway Airport start from $188 round-trip. Over the 12 Southwest flights for this route in a normal week, average airfare is usually $359 round-trip - but some users have found much cheaper deals with momondo.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Fort Myers to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Fort Myers.
Can I find flights from Fort Myers to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Fort Myers to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Fort Myers to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Fort Myers. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Fort Myers to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Fort Myers to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.