$77 Cheap Flights from Fort Myers (RSW) to Chicago (MDW)

View $77 flight on Sun, Sep 7, 2025Opens in a new window

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

Prices were available within the past 7 days and start at $77 for one-way flights and $154 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, Sep 7 - Thu, Sep 11
RSW
Fort Myers
MDW
Chicago
$154 Roundtrip, found 1 hour ago
$154
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Sep 7 from Fort Myers to Chicago, returning Thu, Sep 11, priced at $154 found 1 hour ago
Southwest Airlines
Wed, Oct 8 - Sun, Oct 12
RSW
Fort Myers
MDW
Chicago
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 8 from Fort Myers to Chicago, returning Sun, Oct 12, priced at $156 found 1 day ago
Southwest Airlines
Wed, Oct 22 - Tue, Oct 28
RSW
Fort Myers
MDW
Chicago
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Fort Myers to Chicago, returning Tue, Oct 28, priced at $157 found 1 day ago
Southwest Airlines
Wed, Oct 1 - Sun, Oct 5
RSW
Fort Myers
MDW
Chicago
$158 Roundtrip, found 10 hours ago
$158
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Fort Myers to Chicago, returning Sun, Oct 5, priced at $158 found 10 hours ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
RSW
Fort Myers
MDW
Chicago
$159 Roundtrip, found 11 hours ago
$159
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Nov 13 from Fort Myers to Chicago, returning Sun, Nov 16, priced at $159 found 11 hours ago
Frontier Airlines
Thu, Oct 30 - Tue, Nov 4
RSW
Fort Myers
MDW
Chicago
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Fort Myers to Chicago, returning Tue, Nov 4, priced at $162 found 3 days ago
Frontier Airlines
Thu, Sep 25 - Sun, Sep 28
RSW
Fort Myers
MDW
Chicago
$163 Roundtrip, found 6 hours ago
$163
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Sep 25 from Fort Myers to Chicago, returning Sun, Sep 28, priced at $163 found 6 hours ago
Southwest Airlines
Wed, Nov 12 - Sun, Nov 16
RSW
Fort Myers
MDW
Chicago
$170 Roundtrip, found 11 hours ago
$170
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Nov 12 from Fort Myers to Chicago, returning Sun, Nov 16, priced at $170 found 11 hours ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
RSW
Fort Myers
MDW
Chicago
$171 Roundtrip, found 11 hours ago
$171
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Nov 13 from Fort Myers to Chicago, returning Sun, Nov 16, priced at $171 found 11 hours ago
Delta
Mon, Sep 22 - Thu, Sep 25
RSW
Fort Myers
MDW
Chicago
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep 22 from Fort Myers to Chicago, returning Thu, Sep 25, priced at $194 found 2 days ago
Flights from Fort Myers (RSW) to Chicago (MDW)
Origin airport
Southwest Florida Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$154
Distance
1107 mi
Average flight time
1 hour 50 mins

Fort Myers to Chicago Flights

The cheapest times to fly from Fort Myers to Chicago

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 Fort Myers to Chicago are during the month of September. You can find some of the cheapest flights from Fort Myers to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Fort Myers to Chicago: 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 Fort Myers to Chicago

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 Fort Myers to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $77 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 Fort Myers to Chicago 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 Fort Myers to Chicago 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.

 

Frequently asked questions

How much does a flight from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $77 or cheap return flight from $154 from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
The cheapest month to fly from RSW to MDW is September, when demand is low. Off-peak months are typically when airlines offer better prices between these airports.
Which airlines fly direct from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
Take a direct flight with Southwest Airlines and go straight from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from RSW to MDW, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
When flying out of Southwest Florida Intl. Airport (RSW), you can take your pick from an average of 3 daily direct flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
The 7 AM departures from RSW to MDW see the highest demand. They can also be more expensive. If you want to save on your trip, choose a less crowded time to fly.
What day of the week has the most flights from RSW to MDW?
Fly on a Friday if you're after the best selection of flights from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW).
What is the earliest flight from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
Southwest Florida Intl. Airport (RSW)'s first flight to Midway Intl. Airport (MDW) takes off at approximately 6:20AM UTC-5. With a total travel time of 3h, you'll touch down at around 8:20AM UTC-6.
How long does it take to fly from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
It takes around 3 hours and 1 minute to cover the 1,100 mi from RSW to MDW.
What is the best time to fly from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) without delays, pick a flight that takes off from Southwest Florida Intl. Airport (RSW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Southwest Florida Intl. Airport (RSW)?
If you're traveling on a direct flight from Southwest Florida Intl. Airport (RSW) to Chicago, you'll come into land at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from RSW to MDW just before your getaway is typically more expensive. However, if there's some wiggle room with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a RSW to MDW flight and hotel package?
You'll generally save money by booking a RSW to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've chosen your ideal flights and accommodations, you can add extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
If you reserved your RSW to MDW flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you purchased, 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 for further details.

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*Available to One Key members.