MDW - RSW

$90 Find Cheap Flights from Chicago Midway Airport to Fort Myers

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 7/4. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Fort Myers

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Fort Myers, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Fort Myers, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Midway to Fort Myers

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Fort Myers.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
10:25 am - 4:15 pmMDW-RSW
4h 50m1 stop
Delta Logo
5:30 am - 9:40 amRSW-MDW
5h 10m1 stop
$217Delta
Find Deal
Sat, May 31 - Sat, Jun 7
Southwest Logo
6:20 pm - 10:05 pmMDW-RSW
2h 45mnonstop
Southwest Logo
6:00 pm - 11:00 pmRSW-MDW
6h 00m1 stop
$227Southwest
Find Deal
Tue, Jun 3 - Tue, Jun 10
Southwest Logo
6:20 pm - 10:05 pmMDW-RSW
2h 45mnonstop
Southwest Logo
6:20 pm - 10:00 pmRSW-MDW
4h 40m1 stop
$228Southwest
Find Deal
Wed, May 21 - Sun, May 25
Delta Logo
1:55 pm - 11:13 pmMDW-RSW
8h 18m1 stop
Delta Logo
5:30 am - 9:40 amRSW-MDW
5h 10m1 stop
$230Delta
Find Deal
Wed, May 21 - Sun, May 25
Delta Logo
6:00 am - 2:02 pmMDW-RSW
7h 02m1 stop
Delta Logo
5:30 am - 9:40 amRSW-MDW
5h 10m1 stop
$237Delta
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
4:15 pm - 11:37 pmMDW-RSW
6h 22m1 stop
Delta Logo
3:29 pm - 9:45 pmRSW-MDW
7h 16m1 stop
$247Delta
Find Deal
Sat, May 17 - Wed, Jun 11
Southwest Logo
1:05 pm - 4:50 pmMDW-RSW
2h 45mnonstop
Southwest Logo
7:15 am - 9:10 amRSW-MDW
2h 55mnonstop
$250Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
Southwest Logo
8:20 pm - 12:05 amMDW-RSW
2h 45mnonstop
Southwest Logo
6:40 am - 3:50 pmRSW-MDW
10h 10m1 stop
$253Southwest
Find Deal
Thu, Jul 24 - Tue, Jul 29
Frontier Logo
6:20 am - 6:19 pmMDW-RSW
10h 59m1 stop
Frontier Logo
7:16 pm - 11:17 pmRSW-MDW
5h 01m1 stop
$342Frontier
Find Deal
Thu, Jul 3 - Sun, Jul 6
Frontier Logo
6:20 am - 6:19 pmMDW-RSW
10h 59m1 stop
Frontier Logo
7:16 pm - 11:18 pmRSW-MDW
5h 02m1 stop
$392Frontier
Find Deal
Thu, Jun 12 - Sun, Jun 15
Useful Info

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.

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, Tuesday is the most expensive day to fly from Chicago Midway Airport to Fort Myers. For your return ticket, we recommend flying on a Friday 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 September, where tickets cost $240 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $516 and $486 respectively.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonJuly
High seasonMarch
Cheapest flight$90
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 34% increase in price.
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 3 days, the lowest price for a flight from Chicago Midway Airport to Fort Myers was $90 for a one-way ticket and $217 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, 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 Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Fort Myers flight route.

  • 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 $406 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 $356 and an overall rating of 8.0.

  • 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 $131 or less one-way and $237 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?

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
See more direct flights

Top 4 airlines serving 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 4294 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

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.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

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

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

A bit rush for transit. Food and entertainment are not available

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.