$59 Find Cheap Flights from Chicago Midway Airport to Florida

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 Florida departing on 4/13. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida.
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Flight Deals

Cheap Flights from Midway to Florida

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Orlando
Orlando1 stop$132
Miami
Miami1 stop$136
Fort Lauderdale
Fort Lauderdale1 stop$140
Tampa
Tampa1 stop$134
Fort Myers
Fort Myersnonstop$291
West Palm Beach
West Palm Beach1 stop$269
Jacksonville
Jacksonville1 stop$258
Sarasota
Sarasotanonstop$257
Pensacola
Pensacola1 stop$269
Key West
Key West1 stop$315
Panama City
Panama Citynonstop$271
Valparaiso
Valparaisononstop$90
Punta Gorda
Punta Gordanonstop$77
Tallahassee
Tallahassee1 stop$357
Gainesville
Gainesville1 stop$443
Orlando
Orlando1 stop$132
Miami
Miami1 stop$136
Fort Lauderdale
Fort Lauderdale1 stop$140
Tampa
Tampa1 stop$134
Fort Myers
Fort Myersnonstop$291
West Palm Beach
West Palm Beach1 stop$269
Jacksonville
Jacksonville1 stop$258
Sarasota
Sarasotanonstop$257
Pensacola
Pensacola1 stop$269
Key West
Key West1 stop$315
Panama City
Panama Citynonstop$271
Valparaiso
Valparaisononstop$90
Punta Gorda
Punta Gordanonstop$77
Tallahassee
Tallahassee1 stop$357
Gainesville
Gainesville1 stop$443

Book Cheap Midway to Florida Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Florida 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 Florida

Wed, Apr 22 - Wed, Apr 29
Multiple Airlines Logo
6:15 am - 3:29 pm
MDW
-
MCO
8h 14m
1 stop
Multiple Airlines Logo
2:40 pm - 10:14 pm
MCO
-
MDW
8h 34m
1 stop
$132Multiple Airlines
Mon, Apr 20 - Wed, Apr 22
Multiple Airlines Logo
6:00 am - 3:29 pm
MDW
-
MCO
8h 29m
1 stop
Multiple Airlines Logo
11:18 am - 7:31 pm
MCO
-
MDW
9h 13m
1 stop
$133Multiple Airlines
Fri, May 8 - Tue, May 12
Frontier Logo
4:52 pm - 8:39 pm
MDW
-
MCO
2h 47mnonstop
Frontier Logo
5:10 pm - 10:02 pm
MCO
-
MDW
5h 52m
1 stop
$134Frontier
Wed, Apr 22 - Tue, Apr 28
Multiple Airlines Logo
2:15 pm - 4:57 pm
MDW
-
TPA
25h 42m
1 stop
Multiple Airlines Logo
6:02 pm - 10:14 pm
TPA
-
MDW
5h 12m
1 stop
$134Multiple Airlines
Tue, Apr 21 - Fri, Apr 24
Multiple Airlines Logo
2:15 pm - 10:24 am
MDW
-
MCO
19h 09m
1 stop
Multiple Airlines Logo
11:18 am - 7:31 pm
MCO
-
MDW
9h 13m
1 stop
$135Multiple Airlines
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
2:15 pm - 10:02 am
MDW
-
MIA
18h 47m
1 stop
Frontier Logo
1:05 pm - 7:31 pm
MIA
-
MDW
7h 26m
1 stop
$136Frontier
Thu, May 7 - Sat, May 9
Southwest Logo
6:55 pm - 10:30 pm
MDW
-
SRQ
2h 35mnonstop
Southwest Logo
3:15 pm - 5:05 pm
SRQ
-
MDW
2h 50mnonstop
$257Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
4:50 pm - 9:30 pm
MDW
-
JAX
3h 40m
1 stop
Southwest Logo
7:35 am - 2:40 pm
JAX
-
MDW
8h 05m
2 stops
$258Southwest
Tue, May 12 - Mon, May 18
Delta Logo
5:10 pm - 10:26 pm
MDW
-
JAX
4h 16m
1 stop
Delta Logo
5:38 pm - 9:09 pm
JAX
-
MDW
4h 31m
1 stop
$262Delta
Sat, May 16 - Thu, May 28
Delta Logo
6:23 am - 11:48 am
MDW
-
SRQ
4h 25m
1 stop
Delta Logo
3:09 pm - 9:09 pm
SRQ
-
MDW
7h 00m
1 stop
$267Delta
Booking Insights

KAYAK's insights & trends for Midway to Florida flights

Get data-powered insights and trends into flights from Midway to Florida 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 Florida?

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 Florida departing in April.

What is the cheapest Chicago Midway Airport to Florida flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Florida from Chicago Midway Airport found in the last 72 hours was to Miami, at $125 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Orlando Airport (MCO), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $146.

What is the cheapest time of day to fly to Florida?

The average price for all round-trip flights from Chicago Midway Airport to Florida depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida is generally at night, when round-trip flights cost $260 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Florida is generally in the morning, which is peak travel time and where the average cost of a ticket is $291.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $173 on average.

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

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 Florida, 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 Florida is September, when tickets cost $193 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $367 and $356 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Florida on a Thursday and more expensive on a Wednesday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Tuesdays for better deals.

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

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 Florida, 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 Florida, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$49
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to Miami

FAQs - booking Florida flights

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

    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 Florida.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Florida 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 Florida?

    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 from Chicago Midway Airport to Florida with an airline and back with another airline.

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

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

Top tips for finding cheap flights to Florida

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Orlando $162 one-way - $242 round-trip; Miami $127 one-way - $179 round-trip; Tampa $186 one-way - $313 round-trip

Reviews of the top 5 airlines serving from Midway to Florida

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Florida. 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 Florida? 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 4338 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
Airline reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

2.0 MediocreJames, Apr 2026
LAX - MCO
Read more Southwest reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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.

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

N Everything was perfect from boarding to assistance to baggage in Tampa

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.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

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

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

Not totally their fault- screaming kids that had zero parent intervention.

It was cold on the flight. The crew was very pleasant. I didn't order any food. We were delayed due to Captain waiting on maintenance log. He kept us informed though. The flight itself was smooth. I would definitely fly with Allegiant again!

I had a fantastic experience with Allegiant. I had wheelchair assistance and they helped me find my luggage and brought me to my car. Even loaded my luggage. Wonderful service!! Thank you Allegiant!

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

There is not one likable thing about this airline. It’s starts with the deceptive pricing and continues through the whole flight. The worst staff I’ve ever experienced way over priced bags absolutely no food or drink (unacceptable and you should be embarrassed) the seats are cramped and uncomfortable there is no entertainment there is nothing about this trash airline that constitutes any amount of money. It’s worse than spirit and way more expensive it is disgraceful. Do not travel with Allegiant I repeat do not bother no matter what they say the price is it is never ever going to be the right choice I’m mind blown at how awful the entire experience was I’m embarrassed that I chose so poorly I cannot reiterate enough how beyond horrible this company and its staff are, not one person on this flight or at the airport is qualified to sweep up trash on a city sidewalk they should certainly never be given any job that requires a brain or manners or communication with human beings, what a disgrace to the human race. Your criminal chiselers and should be put out to pasture

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

They cancelled my flight with no reason affecting my travel plans and delaying it 24 hours.

Everything was horrible. They delayed my flight so I missed my connection flight and I lost my bags. I had to go to the same workers multiple times asking the same questions because everyone kept giving me different answers. One person closed down customer service because he wanted to go on lunch so there was like 30 people just waiting for hours because no one would relieve him.

Landing was technically perfect. What I didn't like is the pricey internet. Both flights with excellent crews. I'm 6 feet 210 pounds and could easily fit in the chair.

First flight in along time with spirit! I’m honored to say this flight was excellent 😊

Every connection was late but that meant I was not running from one to the next so that was a good thing. No one wants to miss a connection

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

Better than expected. Staff were friendly and nice on both flights.

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

Everything you need to know for your flight from Midway to Florida

Information on your arrival and departure airports