Cheap Flight Tickets from Fort Myers (RSW) to Chicago (MDW), Starting at $271

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

$279

WN Southwest Airlines • 1 stop • 8h 30m

Oct 16 – Oct 18

The cheapest round trip flight from Fort Myers to Chicago (RSW-MDW-RSW) is currently $279

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Cheapest Direct Flight

$271

WN Southwest Airlines • nonstop • 4h 10m

Oct 16

The cheapest nonstop flight from Fort Myers to Chicago (RSW-MDW) is currently $271

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Fastest Flight

4h 10m

The fastest nonstop flight from Fort Myers to Chicago (RSW-MDW) takes 4h 10m

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.

Oct 16 - Oct 18, Economy
WN
Fort Myers → Chicago
8h 30m
5:50 AM - 10:00 AM • 1 stop
WN
Fort Myers → Chicago
4h 5m
8:10 AM - 11:55 AM • nonstop
$279
Southwest Airlines
Oct 16 - Oct 18, Economy
WN
Fort Myers → Chicago
10h 30m
2:25 PM - 7:55 PM • 1 stop
WN
Fort Myers → Chicago
4h 5m
8:10 AM - 11:55 AM • nonstop
$279
Southwest Airlines
Oct 16 - Oct 18, Economy
WN
Fort Myers → Chicago
12h 25m
6:00 AM - 12:45 PM • 1 stop
WN
Fort Myers → Chicago
4h 5m
1:00 PM - 4:45 PM • nonstop
$279
Southwest Airlines
Oct 16 - Oct 18, Economy
WN
Fort Myers → Chicago
13h 50m
4:45 PM - 12:15 AM • 1 stop
WN
Fort Myers → Chicago
4h 5m
1:00 PM - 4:45 PM • nonstop
$279
Southwest Airlines
Oct 16 - Oct 18, Economy
WN
Fort Myers → Chicago
12h 35m
5:50 AM - 12:45 PM • 2 stops
WN
Fort Myers → Chicago
4h 5m
7:00 PM - 10:45 PM • nonstop
$283
Southwest Airlines
Oct 16 - Oct 18, Economy
DL
Fort Myers → Chicago
18h 31m
6:36 AM - 4:47 PM • 1 stop
DL
Fort Myers → Chicago
11h 42m
1:27 PM - 9:29 PM • 1 stop
$292
Delta 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 5:50 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 279
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 6:40 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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