MDW - RSW

$141 Find Cheap Flights from Chicago Midway Airport to Fort Myers - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Fort Myers departing on 8/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$283
Typical prices: $271-$385
Southwest
Sat 10/17Wed 10/21
MDW - RSW • Non-stop
Cheapest one-way
$141
Typical prices: $148-$443
Frontier
Sat 8/29
MDW - RSW • 2 stops
Top airlines
Cheapest • from $283 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 45m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top layover airports
Cheapest • Avg $336 (round-trip)
Shortest trip • 4h 20m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
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Good to know
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Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Fort Myers that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Fort Myers

Sat, Oct 17 - Wed, Oct 21
Southwest Logo
4:10 pm - 7:55 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
12:25 pm - 2:15 pm
RSW
-
MDW
2h 50mnonstop
$283Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
6:00 pm - 9:50 pm
MDW
-
RSW
2h 50mnonstop
Southwest Logo
5:40 pm - 7:30 pm
RSW
-
MDW
2h 50mnonstop
$283Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
3:05 pm - 6:55 pm
MDW
-
RSW
2h 50mnonstop
Southwest Logo
8:15 am - 10:00 am
RSW
-
MDW
2h 45mnonstop
$283Southwest
Wed, Sep 9 - Mon, Sep 14
Southwest Logo
6:00 pm - 9:50 pm
MDW
-
RSW
2h 50mnonstop
Southwest Logo
6:50 am - 8:40 am
RSW
-
MDW
2h 50mnonstop
$283Southwest
Mon, Sep 28 - Wed, Sep 30
Southwest Logo
6:15 pm - 10:05 pm
MDW
-
RSW
2h 50mnonstop
Southwest Logo
7:10 am - 8:55 am
RSW
-
MDW
2h 45mnonstop
$283Southwest
Sat, Aug 22 - Sat, Sep 5
Delta Logo
4:39 pm - 12:40 am
MDW
-
RSW
7h 01m
1 stop
Delta Logo
12:22 pm - 4:59 pm
RSW
-
MDW
5h 37m
1 stop
$303Delta
Sat, Oct 10 - Sat, Oct 17
Delta Logo
11:33 am - 6:50 pm
MDW
-
RSW
6h 17m
1 stop
Delta Logo
2:10 pm - 6:00 pm
RSW
-
MDW
4h 50m
1 stop
$303Delta
Wed, Aug 19 - Thu, Aug 20
Delta Logo
12:46 pm - 6:58 pm
MDW
-
RSW
5h 12m
1 stop
Delta Logo
6:46 am - 11:51 am
RSW
-
MDW
6h 05m
1 stop
$303Delta
Sat, Oct 24 - Sat, Oct 31
Delta Logo
9:29 am - 5:25 pm
MDW
-
RSW
6h 56m
1 stop
Delta Logo
7:00 am - 10:37 am
RSW
-
MDW
4h 37m
1 stop
$303Delta
Tue, Aug 11 - Fri, Aug 14
Frontier Logo
11:06 am - 10:43 am
MDW
-
RSW
46h 37m
2 stops
Frontier Logo
11:38 am - 9:51 am
RSW
-
MDW
47h 13m
2 stops
$523Frontier
Booking Insights

KAYAK's insights & trends for Midway to Fort Myers flights

Get data-powered insights and trends into flights from Midway to Fort Myers to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago Midway Airport to Fort Myers?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Fort Myers departing in September.

Flight prices are below average for this route right now.

Flights to Fort Myers from Chicago Midway Airport usually cost between $315 and $342 in September.
The lowest price found in the past 5 days was $283 on Southwest (Sep 12-Sep 19).

What’s the cheapest day of the week to fly from Chicago Midway Airport to Fort Myers?

The average price of all round-trip flights from Chicago Midway Airport to Fort Myers clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Fort Myers on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Fort Myers. For your return ticket, we recommend flying on a Thursday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Chicago Midway Airport to Fort Myers?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Fort Myers, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Fort Myers is January, where tickets cost $264 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $520 and $467 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Fort Myers?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $391, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago Midway Airport to Fort Myers?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Fort Myers, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Fort Myers, you should book around 4 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low season

August

Cheapest flight

$141
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago Midway Airport to Fort Myers

When to book flights from Midway to Fort Myers

Are your dates flexible? Find out the best times to travel from Midway to Fort Myers based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Fort Myers flights

  • Southwest Airlines, the only provider with direct flights from Chicago Midway Airport to Fort Myers, has an Inflight Entertainment Portal featuring free movies, TV series, a flight tracker, texting, and live TV. It also has in-seat power with USB-A and USB-C ports to charge your device onboard.

    Chicago Midway International Airport (MDW) is ADA-compliant. Travelers with reduced mobility flying through the airport can access several services and amenities, including wheelchair assistance, dedicated lanes, elevators, accessible restrooms, and accessible parking spaces. For wheelchair help, contact your airline at least 48 hours before your trip or when making a reservation.

  • How do I get to downtown Fort Myers from Southwest Florida International Airport (RSW)?

    Public bus Route 50, run by LeeTran, provides connections to Daniels Parkway and U.S. 41, where you can connect to other routes. The journey time is around 1h 4 min, including a layover time of around 17 minutes. Different rental companies are available onsite in the Ground Transportation area. You can also opt for a taxi or hotel shuttle.

  • What airlines have eco-friendly flights from Chicago Midway Airport to Fort Myers?

    For sustainable flights from Chicago Midway Airport to Fort Myers, you can book Southwest Airlines, which has a direct flight with reduced carbon emissions. It emits 6% less CO₂ than a typical flight on this route. The airline has adopted several sustainable practices in its operations to lower greenhouse gas emissions.

  • Which airline offers unaccompanied minor service on flights from Chicago Midway Airport to Fort Myers?

    If you have a minor flying alone, consider booking Southwest Airlines, which offers an unaccompanied minor service on its direct flights at a fee. This service is mandatory for children aged 5 to 11. Your child will be escorted to the flight by a Southwest Airlines employee, receive the necessary assistance onboard, and be escorted to the person picking them up upon arrival.

  • What is the cheapest flight from Chicago Midway Airport to Fort Myers?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Fort Myers was $141 for a one-way ticket and $283 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Fort Myers?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Fort Myers?

    American Airlines, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Chicago Midway Airport to Fort Myers flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Fort Myers?

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Fort Myers flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to Fort Myers?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Fort Myers.

  • On which days can I fly direct from Chicago Midway Airport to Fort Myers?

    There are nonstop flights from Chicago Midway Airport to Fort Myers on a daily basis.

  • Which is the best airline for flights from Chicago to Fort Myers, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Fort Myers are Southwest and Delta. With an average price for the route of $388 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $355 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Fort Myers?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Fort Myers.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Fort Myers?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Fort Myers from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Fort Myers?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Fort Myers with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and RSW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Fort Myers?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Fort Myers from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Fort Myers

  • Looking for a cheap flight? 25% of our users found flights on this route for $147 or less one-way and $295 or less round-trip.
  • Which other cities can I fly to from Melbourne?
  • From Melbourne, you can extend your trip to domestic destinations like Sydney, Brisbane, Perth, Canberra, Adelaide, Gold Coast, Cairns, and Hobart or international destinations like Singapore, Auckland, Hong Kong, Dubai, Los Angeles, London, Tokyo, and Bangkok. Melbourne Tullamarine Airport (MEL) serves several domestic and international airlines with flights to these destinations.
  • The Chicago Midway Airport (MDW) to Fort Myers (RSW) flight route features several direct and connecting flights. Popular layover cities for one-stop flights on this route include Philadelphia (PHL), Atlanta (ATL), Pittsburgh (PIT), Orlando (MCO), Nashville (BNA), and Washington D.C. (WAS). The layover city depends on the flight route.
  • Southwest Airlines and Delta Airlines have no maximum carry-on weight limit on their direct flights from Chicago Midway Airport to Fort Myers. You can bring one hand baggage and one personal item not exceeding certain dimensions onboard. The hand baggage must fit in the overhead compartment, while the personal item should fit beneath the seat in front of you.
  • For Business Class flights from Chicago Midway Airport to Fort Myers, you can book Delta Airlines, which has this travel option on its one-stop flights. Delta Airlines offers several benefits on its Business Class flights, including spacious seating, access to Delta Sky Club lounges, premium dining, priority check-in and boarding, and special baggage allowance.

Prefer to fly direct from Chicago Midway Airport to Fort Myers?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Fort Myers SW Florida Intl.
Find which airlines fly direct from Chicago Midway Airport to Fort Myers SW Florida Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Fort Myers SW Florida Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Fort Myers SW Florida Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Midway to Fort Myers

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Fort Myers. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Fort Myers? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4229 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Excellent experience. WiFi worked on this leg of My trip

The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

Boarding and deboarding painfully slow. Southwest is typically delayed in my experience.

friendly staff for the most part. they thought we were going to have bad turbulence so no drink service. there wasn't any turbulence. Iwish you had a choice of snacks

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

They did a fine job. Can't wait to use Delta in the future.

Everything you need to know for your flight from Midway to Fort Myers

Information on your arrival and departure airports