$53 Find Cheap Flights from Chicago to Fort Myers Beach

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Fort Myers Beach departing on 7/21. 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.
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Cheap Flights from Chicago to Fort Myers Beach (CHI-RSW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Fort Myers Beach 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 Chicago to Fort Myers Beach

Wed, Jul 9 - Fri, Jul 11
Spirit Airlines Logo
3:18 pm - 7:12 pmORD-RSW
2h 54mnonstop
Spirit Airlines Logo
9:34 pm - 11:44 pmRSW-ORD
3h 10mnonstop
$102Spirit Airlines
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Wed, Jul 9 - Fri, Jul 11
Spirit Airlines Logo
3:18 pm - 7:12 pmORD-RSW
2h 54mnonstop
Spirit Airlines Logo
9:34 pm - 11:44 pmRSW-ORD
3h 10mnonstop
$104Spirit Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
Southwest Logo
7:50 am - 11:30 amMDW-RSW
2h 40mnonstop
Southwest Logo
4:20 pm - 6:10 pmRSW-MDW
2h 50mnonstop
$157Southwest
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Sun, Aug 24 - Sat, Aug 30
Southwest Logo
6:55 pm - 10:40 pmMDW-RSW
2h 45mnonstop
Southwest Logo
4:25 pm - 6:15 pmRSW-MDW
2h 50mnonstop
$158Southwest
Find Deal
Tue, Jul 8 - Tue, Jul 15
United Airlines Logo
7:15 am - 11:20 amORD-RSW
3h 05mnonstop
United Airlines Logo
12:26 pm - 2:39 pmRSW-ORD
3h 13mnonstop
$169United Airlines
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Fri, Aug 29 - Fri, Aug 29
American Airlines Logo
6:50 am - 10:42 amORD-RSW
2h 52mnonstop
American Airlines Logo
11:48 am - 2:05 pmRSW-ORD
3h 17mnonstop
$173American Airlines
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Wed, Aug 13 - Mon, Aug 18
United Airlines Logo
10:57 am - 3:02 pmORD-RSW
3h 05mnonstop
United Airlines Logo
4:36 pm - 6:55 pmRSW-ORD
3h 19mnonstop
$177United Airlines
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Tue, Jul 1 - Fri, Jul 11
American Airlines Logo
8:05 am - 11:57 amORD-RSW
2h 52mnonstop
American Airlines Logo
4:26 pm - 6:41 pmRSW-ORD
3h 15mnonstop
$194American Airlines
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Thu, Aug 7 - Sun, Aug 10
Frontier Logo
6:20 am - 6:20 pmMDW-RSW
11h 00m1 stop
Frontier Logo
7:16 pm - 11:17 pmRSW-MDW
5h 01m1 stop
$234Frontier
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Sun, Aug 31 - Sun, Sep 7
Frontier Logo
11:03 am - 6:24 pmMDW-RSW
6h 21m1 stop
Frontier Logo
7:13 pm - 11:25 pmRSW-MDW
5h 12m1 stop
$235Frontier
Find Deal
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Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$53
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 46% increase in price.
Flight from Chicago O'Hare Airport to Fort Myers

When to book flights from Chicago to Fort Myers Beach

Are your dates flexible? Find out the best times to travel from Chicago to Fort Myers Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Fort Myers Beach

  • Which airports will I be using when flying from Chicago to Fort Myers Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Fort Myers Beach does not have its own airport so you’ll be flying into nearby Fort Myers SW Florida Intl airport, which is 13.1 mi away.

  • How long does a flight from Chicago to Fort Myers Beach take?

    Direct flights cover the 1,110 miles separating Chicago and Fort Myers Beach in about 2h 40m.

  • How many flights are there between Chicago and Fort Myers Beach?

    19 direct flights run between Chicago and Fort Myers Beach on a daily basis. On average, there are about 133 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Fort Myers Beach?

    Consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

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

    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 to Fort Myers Beach.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Fort Myers Beach from Chicago 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 to Fort Myers Beach?

    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 Beach with an airline and back to Chicago with another airline.

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

    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 Beach from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Fort Myers Beach?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Fort Myers Beach found on KAYAK was with Spirit Airlines for $53. Spirit Airlines offered a round-trip connection from $102 and Southwest from $157.

Top tips for finding cheap flights from Chicago to Fort Myers Beach

  • There is no airport in Fort Myers Beach. Instead, you’ll be flying into SW Florida Intl Airport when flying between Chicago and Fort Myers Beach.
  • The cheapest flight from Chicago to Fort Myers Beach was found 49 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is August.

Top 5 airlines serving Chicago to Fort Myers Beach

 
Need help choosing which airline to fly with from Chicago to Fort Myers Beach? 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 4287 reviews
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
Airline reviews

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

6.0 GoodVincent, May 2025MDW - MCO
Read more Southwest reviews

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

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.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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

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.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

My experience with spirit was terrible. Customer service was terrible. Flight got canceled abruptly with no accommodations made for the inconvenience or any sort of help. I was unable to rebook a new flight.

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

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

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