Cheap Flight Tickets from Fort Myers (RSW) to Chicago (MDW), Starting at $121

Good to Know: Cheapest and Fastest RSW - MDW Flights

Useful information for finding best airline tickets from Southwest Florida International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$376

WN Southwest Airlines • 1 stop • 13h 45m

Dec 16 – Dec 27

The cheapest round trip flight from Fort Myers to Chicago (RSW-MDW-RSW) is currently $376

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Cheapest One way Flight

$121

WN Southwest Airlines • 2 stops • 14h 5m

Aug 09

The cheapest one way flight from Fort Myers to Chicago (RSW-MDW) is currently $121

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Cheapest Direct Flight

$335

WN Southwest Airlines • nonstop • 4h 15m

Dec 17

The cheapest nonstop flight from Fort Myers to Chicago (RSW-MDW) is currently $335

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Fastest Flight

4h 15m

The fastest nonstop flight from Fort Myers to Chicago (RSW-MDW) takes 4h 15m

Top Airlines Flying from Fort Myers to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from Fort Myers (RSW) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Fort Myers to Chicago. Ideal for travelers with confirmed return itineraries.

Dec 16 - Dec 27, Economy
WN
Fort Myers → Chicago
13h 45m
10:00 AM - 5:25 PM • 1 stop
WN
Fort Myers → Chicago
4h
1:00 PM - 4:40 PM • nonstop
$376
Southwest Airlines
Dec 17 - Dec 28, Economy
WN
Fort Myers → Chicago
18h 25m
6:30 AM - 4:35 PM • 1 stop
WN
Fort Myers → Chicago
17h 25m
12:45 PM - 12:30 AM • 2 stops
$426
Southwest Airlines
Dec 16 - Dec 27, Economy
WN
Fort Myers → Chicago
17h 15m
11:55 AM - 9:30 PM • 1 stop
WN
Fort Myers → Chicago
17h 35m
9:35 PM - 9:30 AM • 1 stop
$585
Southwest Airlines
Dec 16 - Dec 27, Economy
WN
Fort Myers → Chicago
14h 10m
1:35 PM - 9:25 PM • 1 stop
WN
Fort Myers → Chicago
4h 5m
7:50 PM - 11:35 PM • nonstop
$595
Southwest Airlines
Dec 16 - Dec 27, Economy
WN
Fort Myers → Chicago
11h 50m
1:35 PM - 7:45 PM • 2 stops
WN
Fort Myers → Chicago
4h 5m
7:50 PM - 11:35 PM • nonstop
$600
Southwest Airlines
Dec 16 - Dec 27, Economy
WN
Fort Myers → Chicago
22h
7:10 AM - 7:30 PM • 1 stop
WN
Fort Myers → Chicago
4h 5m
7:50 PM - 11:35 PM • nonstop
$631
Southwest Airlines

Fly from Fort Myers to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Fort Myers to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Fort Myers to Chicago Flights

What are the airports in Fort Myers?
RSW
What’s the most popular airline flying from RSW to MDW?
The most popular airline flying from Fort Myers to Chicago are
Can I fly from RSW to MDW non-stop?
Yes, you can fly RSW to MDW non-stop on
Which airlines fly nonstop between Fort Myers and Chicago?
The non-stop flights between Fort Myers and Chicago are .
What’s the earliest departure time from RSW to MDW Airport?
The earliest flight leaves RSW at 6:10 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Fort Myers to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from RSW to MDW?
Read the fare rules of the Fort Myers to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Fort Myers and Chicago?
operate flights between Fort Myers and Chicago
How long does a flight from Fort Myers to Chicago take?
It takes approximately 3 hour to fly non-stop from RSW to MDW, which is 1105.1 miles by air.
Which airlines provide the cheapest flights from Fort Myers (RSW) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from RSW were found on WN : USD 693
Do I need a passport to fly between RSW and MDW?
No
What’s the latest departure time from RSW to MDW ?
The last flight leaves RSW at 8:00 pm

Fort Myers (RSW) to Chicago (MDW): Airport Information

Origin Airport Southwest Florida International , Fort Myers, US
Destination Airport Chicago Midway International , Chicago, US
Distance 1105 miles

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