$39 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 8/25. 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

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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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Best Florida Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Orlando
Orlandononstop$88
Miami
Miaminonstop$111
Fort Lauderdale
Fort Lauderdalenonstop$132
Tampa
Tampanonstop$91
Fort Myers
Fort Myersnonstop$132
West Palm Beach
West Palm Beach1 stop$150
Jacksonville
Jacksonville1 stop$127
Sarasota
Sarasotanonstop$163
Pensacola
Pensacola1 stop$164
Key West
Key West1 stop$269
Panama City
Panama Citynonstop$197
Valparaiso
Valparaisononstop$87
Punta Gorda
Punta Gordanonstop$78
Tallahassee
Tallahassee1 stop$297
Gainesville
Gainesville1 stop$277
Orlando
Orlandononstop$88
Miami
Miaminonstop$111
Fort Lauderdale
Fort Lauderdalenonstop$132
Tampa
Tampanonstop$91
Fort Myers
Fort Myersnonstop$132
West Palm Beach
West Palm Beach1 stop$150
Jacksonville
Jacksonville1 stop$127
Sarasota
Sarasotanonstop$163
Pensacola
Pensacola1 stop$164
Key West
Key West1 stop$269
Panama City
Panama Citynonstop$197
Valparaiso
Valparaisononstop$87
Punta Gorda
Punta Gordanonstop$78
Tallahassee
Tallahassee1 stop$297
Gainesville
Gainesville1 stop$277

Cheap Flights from Midway to Florida

 
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

Sat, Sep 13 - Sun, Sep 21
Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$88Frontier
Find Deal
Mon, Sep 15 - Sun, Sep 21
Frontier Logo
8:29 am - 12:10 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$89Frontier
Find Deal
Sun, Aug 24 - Mon, Aug 25
Frontier Logo
6:45 am - 10:23 amMDW-TPA
2h 38mnonstop
Frontier Logo
4:18 pm - 6:05 pmTPA-MDW
2h 47mnonstop
$91Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
5:45 am - 7:33 amMCO-MDW
2h 48mnonstop
$93Frontier
Find Deal
Sun, Oct 19 - Sun, Oct 26
Frontier Logo
6:21 am - 10:00 amMDW-TPA
2h 39mnonstop
Frontier Logo
10:55 am - 12:44 pmTPA-MDW
2h 49mnonstop
$97Frontier
Find Deal
Wed, Oct 22 - Mon, Oct 27
Southwest Logo
11:10 am - 8:10 pmMDW-JAX
8h 00m1 stop
Southwest Logo
3:55 pm - 5:20 pmJAX-MDW
2h 25mnonstop
$127Southwest
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Sat, Aug 23 - Sat, Aug 30
Southwest Logo
5:30 pm - 9:25 pmMDW-FLL
2h 55mnonstop
Southwest Logo
4:15 pm - 6:30 pmFLL-MDW
3h 15mnonstop
$132Southwest
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Thu, Aug 28 - Sun, Aug 31
Delta Logo
9:30 am - 4:47 pmMDW-JAX
6h 17m1 stop
Delta Logo
5:01 pm - 9:12 pmJAX-MDW
5h 11m1 stop
$200Delta
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Tue, Aug 12 - Tue, Aug 19
Delta Logo
6:04 am - 1:29 pmMDW-JAX
6h 25m1 stop
Delta Logo
5:01 pm - 9:44 pmJAX-MDW
5h 43m1 stop
$201Delta
Find Deal
Thu, Oct 30 - Sun, Nov 2
Allegiant Air Logo
6:40 pm - 8:55 pmMDW-EYW
25h 15m2 stops
Allegiant Air Logo
8:33 pm - 4:37 pmEYW-MDW
21h 04m2 stops
$373Allegiant Air
Find Deal
Useful Info

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.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Florida.

The cheapest ticket to Florida from Chicago Midway Airport found in the last 72 hours was to Orlando, at $127 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 $127.

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.

No, with an average price for the route of $280, prices are generally cheapest when you fly direct.

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 $173 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $364 and $341 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 4 weeks before departure.


Good to know

Low seasonAugust
High seasonMarch
Cheapest flight$39
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago Midway Airport to Orlando Airport

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.

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

    The cheapest time of day to fly to Florida is generally in the afternoon, when round-trip flights cost $275 on average. Morning departures are around 5% 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 $317.

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 $120 one-way - $178 round-trip; Tampa $108 one-way - $198 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 4257 reviews
7.0Food
8.6Crew
8.2Boarding
7.6Entertainment
8.0Comfort
Airline reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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

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

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

I am very happy with my experience with Spirit Airlines. Both flights were on time. Boarding was very pleasant. Crew was very nice. Flights were amazing and we even arrived earlier than the schedule time. I am hoping Spirits keeps on having non stop flight from Ft Lauderdale to Hartford for many years to come.

you guys canceled my flight last minute and lost my luggage.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

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.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

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!

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