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$98 Cheap Flights from Chicago (MDW) to Fort Myers (RSW)

View $98 flight on Mon, Nov 16, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Southwest Florida Intl. Airport (RSW)

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Cheap Flights from Chicago to Fort Myers (MDW-RSW)

Prices were available within the past 7 days and start at $98 for one-way flights and $195 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Aug 31 - Thu, Sep 3
MDW
Chicago
RSW
Fort Myers
$195 Roundtrip, found 4 hours ago
$195
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Mon, Aug 31 from Chicago to Fort Myers, returning Thu, Sep 3, priced at $195 found 4 hours ago
Southwest Airlines
Wed, Oct 28 - Mon, Nov 2
MDW
Chicago
RSW
Fort Myers
$201 Roundtrip, found 11 hours ago
$201
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Chicago to Fort Myers, returning Mon, Nov 2, priced at $201 found 11 hours ago
Southwest Airlines
Wed, Nov 4 - Mon, Nov 9
MDW
Chicago
RSW
Fort Myers
$205 Roundtrip, found 3 hours ago
$205
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Chicago to Fort Myers, returning Mon, Nov 9, priced at $205 found 3 hours ago
Delta
Wed, Nov 4 - Mon, Nov 9
MDW
Chicago
RSW
Fort Myers
$206 Roundtrip, found 3 hours ago
$206
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Nov 4 from Chicago to Fort Myers, returning Mon, Nov 9, priced at $206 found 3 hours ago
Southwest Airlines
Wed, Nov 4 - Tue, Nov 10
MDW
Chicago
RSW
Fort Myers
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Chicago to Fort Myers, returning Tue, Nov 10, priced at $207 found 1 day ago
Southwest Airlines
Wed, Nov 4 - Mon, Nov 9
MDW
Chicago
RSW
Fort Myers
$210 Roundtrip, found 3 hours ago
$210
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Chicago to Fort Myers, returning Mon, Nov 9, priced at $210 found 3 hours ago
Delta
Tue, Oct 6 - Tue, Oct 13
MDW
Chicago
RSW
Fort Myers
$212 Roundtrip, just found
$212
Roundtrip
just found
Select Delta flight, departing Tue, Oct 6 from Chicago to Fort Myers, returning Tue, Oct 13, priced at $212 just found
Southwest Airlines
Sat, Jan 9 - Sat, Jan 16
MDW
Chicago
RSW
Fort Myers
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jan 9 from Chicago to Fort Myers, returning Sat, Jan 16, priced at $213 found 1 day ago
Southwest Airlines
Tue, Oct 27 - Fri, Oct 30
MDW
Chicago
RSW
Fort Myers
$214 Roundtrip, found 5 hours ago
$214
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Chicago to Fort Myers, returning Fri, Oct 30, priced at $214 found 5 hours ago
Southwest Airlines
Wed, Oct 21 - Mon, Oct 26
MDW
Chicago
RSW
Fort Myers
$215 Roundtrip, just found
$215
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Oct 21 from Chicago to Fort Myers, returning Mon, Oct 26, priced at $215 just found

Alternative airports near Fort Myers

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Southwest Florida Intl. RSW. Cheapest option available. Average driving time to city center is 22 minutes. Flights from $505
RSW
Southwest Florida Intl.
Cheapest
Average driving time to city center22 min
Flights from $505

Find the cheapest month to fly from Chicago (MDW) to Fort Myers (RSW)

September is typically the cheapest month to fly

From $189 - $326 per traveler.

What you need to know for your flight from Midway Intl. to Southwest Florida Intl.

Chicago (MDW) to Fort Myers (RSW) at a glance

Explore a variety of options for flights from Chicago (MDW) to Fort Myers (RSW) on this domestic short-haul route. You can choose between full-service airlines and budget carriers to find the itinerary that suits your financial and scheduling needs while visiting the renowned attractions and neighborhoods of Fort Myers. Discover essential information about flights from Midway International Airport to Southwest Florida International Airport as you plan your getaway.

  • Fastest flight duration: around 2h 45m non-stop
  • Route distance: roughly 1,100 miles (1,770 km)
  • Flights per week: around 13 departures on average
  • Typical fares (one-way): economy tickets often range from $80–$455, depending on seasonality and how far ahead you book

Flights from Midway International Airport (MDW) to Southwest Florida International Airport (RSW)

Based on the latest traveler bookings, here are the top airlines favored by passengers flying from Chicago to Fort Myers, particularly for non-stop and one-stop flights. Popular layover options include Hartsfield-Jackson Atlanta International Airport (ATL), with a layover of about 1 hour and 15 minutes; John Glenn Columbus International Airport (CMH), offering roughly a 55-minute layover; and Indianapolis International Airport (IND), which has a longer layover of approximately 3 hours and 30 minutes. This variety allows you to balance price, travel time, and cabin class for your ideal itinerary.

  • Southwest Airlines: As a budget-friendly airline, it provides both non-stop and one-stop flights with one-way fares generally falling between $80 and $455. This carrier dominates the route with around 94% of departures, and a standard non-stop flight lasts approximately 2 hours and 45 minutes.
  • Delta: This full-service airline offers one-stop options, with one-way ticket prices typically ranging from $110 to $420. Delta accounts for about 5% of the departures on this route, featuring an in-flight duration of 3 hours and 45 minutes and an overall travel time close to 5 hours, including layovers.
  • Frontier Airlines: Another low-cost airline, Frontier provides one-stop services with one-way fares usually between $80 and $170. Representing roughly 1% of departures on this route, travelers can expect 3 hours and 45 minutes of flight time, with total journey duration around 5 hours, factoring in layovers.

Best time to fly from Chicago (MDW) to Fort Myers (RSW)

The most popular months for travelers flying from Chicago to Fort Myers are March, April, and July, when peak temperatures in Fort Myers reach up to 82.9°F in July. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 81.5°F and typically the lowest average one-way fare (around $148). Flight availability peaks in March, with approximately 20 flights per week, making it easier to find convenient departure times. February has the fewest flights, with approximately 9 flights per week.

  • Cheapest time to fly: September usually offers good deals with average one-way fare around $148, roughly 30% cheaper than the yearly average.
  • More budget-friendly months to fly: August and October typically offer average one-way fares of around $154.
  • Most flight options: March has the highest number of flights from Chicago to Fort Myers, with approximately 20 flights per week, giving you more flexibility in scheduling your trip.
calendar iconMonthtemperature iconTemperaturecrowd level iconDemandflights iconWeekly Flightsprice iconAverage one-way Fare
January64.0°F (17.8°C)Average12$193
February67.1°F (19.5°C)Low9$239
March69.4°F (20.8°C)High20$264
April74.8°F (23.8°C)High12$222
May78.4°F (25.8°C)Average11$177
June81.9°F (27.7°C)Low10$236
July82.9°F (28.3°C)High11$174
August83.1°F (28.4°C)Average12$151
September81.5°F (27.5°C)Low11$148
October77.4°F (25.2°C)Average14$158
November71.4°F (21.9°C)Average12$246
December67.6°F (19.8°C)Average14$347

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Chicago (MDW) to Fort Myers (RSW)

  • Chicago to Fort Myers (ORD-RSW): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy ticket prices for this route generally fall between $65 and $405, influenced by the season and advance booking. Flights on this route are typically offered as both non-stop and one-stop options. Major airlines operating this route include United and American Airlines. Additionally, first-class service is available for travelers seeking a premium experience.

How to find the best prices for flights from Chicago (MDW) to Fort Myers (RSW)

Getting some of the best deals on flights from Chicago to Fort Myers is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Afternoon departures from 12 PM to 6 PM often offer lower prices, while morning flights from 5 AM to 12 PM are more popular. Additionally, flying on Thursday typically results in cheaper prices, even though Saturday is the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.* Find Fort Myers hotel and flight deals.
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Southwest Florida International Airport from Midway International Airport

Fort Myers welcomes travelers from Chicago with a range of transport options based on price, convenience, and proximity. Here's how to reach Fort Myers efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Fort Myers, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
  • Car rental: Renting a car from Southwest Florida International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Southwest Florida International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) cost?
You can find cheap one-way flights from $98 and cheap return flights from $195 Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) with Expedia. One-way flights generally range between $142 and $550, and roundtrip flights usually range from $280 to $872. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
The cheapest month to fly from MDW to RSW is August when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
Enter MDW to RSW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
The best airline to fly with from Chicago, IL (MDW) to Fort Myers, FL (RSW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from MDW to RSW, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
On average, there are around 4 nonstop flights per day from Midway Intl. (MDW) to Southwest Florida Intl. (RSW). For more options, look at flights that include layovers.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
The earliest flight from Chicago Midway International Airport (MDW) to Fort Myers (RSW) typically departs at around 5:00 AM, operated by Southwest Airlines. This seasonal service is available in March, making it a great option for early risers heading to sunny Florida. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
The most popular departure times for flights from Chicago Midway (MDW) to Fort Myers (RSW) are in the late morning, from 9am to noon. About 29% of passengers prefer this time window. Many major carriers, including Southwest Airlines and Delta Airlines, offer flights during this window. This timing works well because it allows you to enjoy a full morning in Chicago before your flight.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
A nonstop flight from MDW to RSW typically takes around 2 hours 50 minutes, covering approximately 1,108 miles. Connecting flights on this route usually add 4 hours 30 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
First class seats are offered on the MDW to RSW route with Delta Air Lines.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Fort Myers from Midway Intl. (MDW)?
From Midway Intl. (MDW), you can fly into Southwest Florida Intl. (RSW) to reach Fort Myers. Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Bradley Intl. (BDL), Hartsfield-Jackson Atlanta Intl. (ATL) before reaching Fort Myers. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) Fort Myers Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Southwest Florida Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$195
Distance
1107 mi
Average flight time
3 hours 44 mins

Book with confidence

Chicago to Fort Myers Flights

The cheapest times to fly from Chicago to Fort Myers

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Fort Myers are during the month of August. You can find some of the cheapest flights from Chicago to Fort Myers with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Fort Myers

Sunday is one of the best days to book for cheap flights from Chicago to Fort Myers: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Fort Myers

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Fort Myers in 2026. You can also book with separate airlines for your outbound and return journeys, from $98 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Fort Myers flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Fort Myers airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Fort Myers Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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