Lowest Prices
Uncover the best deals on Fort Myers to Chicago flights by comparing fares from hundreds of airlines and agencies.
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 One way Flight
$110
Southwest Airlines
• 1 stop
• 11h 55m
Sep 20
The cheapest one way flight from Fort Myers to Chicago (RSW-MDW) is currently $110
Fastest Flight
7h 24m
The fastest nonstop flight from Fort Myers to Chicago (RSW-MDW) takes 7h 24m
Top Airlines Flying from Fort Myers to Chicago
Latest Flight Deals from Fort Myers (RSW) to Chicago (MDW)
Explore competitive one-way airfare options for RSW - MDW flights. Best suited for flexible or open-ended travel plans.
Flying to Chicago soon? We've surfaced some of the most affordable last-minute flights from Fort Myers to Chicago, ideal for urgent plans or spontaneous trips.
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?
NO
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 110
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 4:35 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 |
More Flight Options for Fort Myers (RSW) and Chicago (MDW)
Flights from Fort Myers (RSW)
to New York (JFK)
Flights from Fort Myers (RSW)
to Newark (EWR)
Flights from Fort Myers (RSW)
to Newark (EWR)
Flights from Fort Myers (RSW)
to Cincinnati (CVG)
Flights from Fort Myers (RSW)
to New York (LGA)
Flights from Fort Myers (RSW)
to Cleveland (CLE)
Flights from Fort Myers (RSW)
to Seattle (SEA)
Flights from Fort Myers (RSW)
to Omaha (OMA)
Flights from Fort Myers (RSW)
to Philadelphia (PHL)
Flights from Fort Myers (RSW)
to Providence (PVD)
Flights from Fort Myers (RSW)
to Punta Cana (PUJ)
Flights from Fort Myers (RSW)
to Islip (ISP)
Flights from Fort Myers (RSW)
to San Francisco (SFO)
Flights from Fort Myers (RSW)
to Dallas (DAL)
Flights from Fort Myers (RSW)
to New Orleans (MSY)
Flights from Fort Myers (RSW)
to Hartford (BDL)
Flights from Fort Myers (RSW)
to Louisville (SDF)
Flights from Fort Myers (RSW)
to Atlanta (ATL)
Flights from Fort Myers (RSW)
to Chicago (MDW)
Flights from Fort Myers (RSW)
to Phoenix (PHX)
Flights from Portland (PDX)
to Chicago (ORD)
Flights from Newark (EWR)
to Chicago (ORD)
Flights from Newark (EWR)
to Chicago (ORD)
Flights from Phoenix (PHX)
to Chicago (ORD)
Flights from Atlanta (ATL)
to Chicago (ORD)
Flights from Dallas (DFW)
to Chicago (ORD)
Flights from Dallas (DFW)
to Chicago (ORD)
Flights from Minneapolis (MSP)
to Chicago (MDW)
Flights from Minneapolis (MSP)
to Chicago (MDW)
Flights from Los Angeles (LAX)
to Chicago (ORD)
Flights from Fort Lauderdale (FLL)
to Chicago (MDW)
Flights from Boston (BOS)
to Chicago (ORD)
Flights from Minneapolis (MSP)
to Chicago (ORD)
Flights from Minneapolis (MSP)
to Chicago (ORD)
Flights from Dallas (DAL)
to Chicago (MDW)
Flights from Orlando (MCO)
to Chicago (MDW)
Flights from Greensboro (GSO)
to Chicago (ORD)
Flights from Norfolk (ORF)
to Chicago (MDW)
Flights from Orlando (MCO)
to Chicago (ORD)
Flights from Houston (IAH)
to Chicago (ORD)
Cheap flights to North America (NA)
Cheap flights to United States (US)
Cheap flights to Florida (US-FL)
Cheap flights to Illinois (US-IL)
Cheap flights from North America (NA)
Cheap flights from United States (US)
Cheap flights from Florida (US-FL)
Cheap flights from Illinois (US-IL)
Flights to Chicago (MDW)
Flights to Chicago (ORD)
Flights to Fort Myers (RSW)
Flights from Chicago (MDW)
Flights from Chicago (MDW)
to Fort Myers (RSW)
Flights from Chicago (ORD)
Flights from Chicago (ORD)
to Fort Myers (RSW)
Flights from Fort Myers (RSW)
Why Fareleaders for RSW to MDW Plane Tickets
New Deals Everyday
Get the best prices on RSW to MDW flights—we update our fares daily so you never miss a saving.
No Service Fees
Compare hundreds of Fort Myers to Chicago flights and secure the best deals—we never add any service fees.