Find cheap flights from Chicago Midway Airport to Florida

Find cheap flights from Chicago Midway Airport to Florida

Round-trip
Economy
Chicago (MDW)
Florida
Fri 1/15
Fri 1/22
Any month
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Good to know

Low season

January Best time to beat the crowds with an average 5% drop in price.

High season

June Most popular time to fly with an average 17% increase in price.

Average price round-trip

$312 (avg. price over the last 2 weeks)

Good deal round-trip

$174 or less

Good deal one-way

$84 or less

Top tips for finding cheap flights to Florida

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to Florida for the following prices or less: to Fort Lauderdale $97 one-way - $251 round-trip, to Miami $97 one-way - $264 round-trip, to Tampa $92 one-way - $213 round-trip
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Florida is August.
  • Morning departure is around 34% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Florida flights

Which airlines have a flexible cancellation policy for flights from Chicago Midway to Florida due to COVID-19?

How long is the flight to Florida from Chicago Midway?

Are there Florida travel restrictions currently due to Coronavirus?

How does KAYAK find such low prices on flights 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?

What is the Hacker Fare option on flights to Florida?

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

Top airlines flying Chicago Midway to Florida

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,916 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "Delay on flight and providing beverages while waiting for 6 hours"

Pros: "The crew was one of the best I have ever experienced. They even had the flight deck wish a happy birthday to my 89 year old mother in law."

Pros: "I have flown with Delta for a number of trips now. I seem to receive middle seat allocations even with the freqent flyers partnership with Virgin Velosity program shared."
Cons: "My seat allocation."

Pros: "Arrived on time"

Cons: "Stop being LATE!!!!"

Pros: "Great food and service in first class"
Cons: "Water waiting on table on arrival"

Pros: "Full flight, nightmare. No comfort at all. Never again."
Cons: "Comfort on board."

Cons: "At least one hour late"

Pros: "I was trying with a broken arm - the Crew both on the plane and off the plane was wonderful"
Cons: "Would like more food available-not for purchase but with what comes with your flight"

Pros: "Excelente"

Pros: "Television"
Cons: "No drinks or snacks"

Pros: "The seat back screens."
Cons: "Completely full flight. Rough landing."

Cons: "Terminal g18 is in the worst possible place. It is right smack in the middle of a food kiosk and restuarants with the ipad tables. You can't hear any announcements and boarding is just a cluster."

Cons: "6 hours late. Unacceptable."

Cons: "A 7+ hour delay!"

Pros: "The people was relaxed and the flight attendant was polite and professional.. everything was on time"
Cons: "Nothing at all great service"

Pros: "I think they flew so fast. We could land almost on time even though we departed a hour late. Airplane was new and clean."
Cons: "Boarding was chaos. They overbooked 25? 45? Anyway, they are in panic. They tried to request ppl to take next day flight by giving away 300 gift card etc. the ppl who were told there are no seats upset and arguing at the gate. Flight was delayed for one hour. Once we are on airplane, they are still shuffling seats around, so ppl cannot move forward. Just standing there for 10mins waiting for things to settle. Flight attendants did not give us a headphone. (I have a headphone for iPhone X so I could not connect it to their entertaiment system.)"

Cons: "The"

Pros: "Smooth. Fast boarding"

Pros: "Everyone is working the gate and on the plane were amazing!"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "This was my cousins first time flying and the Flight Attendants made her feel very welcomed. They all were very personable."

Pros: "Very nice and courteous crew."
Cons: "Lady at the gate was a bit standoff Ish and the delays were an annoyance."

Pros: "Great crew"

Pros: "Movies"
Cons: "Not supplying headphones Crew not to helpful, one unpolite Refreshments ridiculous"

Pros: "I love Delta. The crew members were very safe, courteous, and efficient."
Cons: "N/a"

Pros: "Delta is always running behind."

Pros: "Trip and flight crew excellent!"
Cons: "I understand that they couldn't deliver luggage during lightening, but my luggage and clothes were soaked!"

Pros: "Enjoy able"
Cons: "Noise"

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "Crew was nice"
Cons: "Always a delay with Delta"

Pros: "From curbside check-in to landing the plane, overall excellent service ! Very pleased to find out they offered a shuttle from checkin to the gate. I am having knee surgery soon and the walk from security to gate 34 LaGuardia would have put me over the top with pain! It was a very nice gentleman that gave me a ride to the gate and even stopped to let me use the bathroom. Thumbs up *****"
Cons: "The fact that I was charged $150 to check a small cosmetics bag is no loose change ! I would have carried it on but my hand is in a brace and I has to have extensive surgery. Then yoy get to the gate, and they repeatedly asked for volunteers to check their bags for free. I think this is a very unfair policy and try to explain it to the curbside attendant. I literally cannot carry more than five pounds in my left hand until I get bone replacement surgery. I'm also having knee surgery soon and this small additional weight would be caused me excruciating pain ! They didn't care and still charged me $150 for a bag thats no bigger than 12 inches and weighs less than ten pounds. Thats the way you treat your first class passengers? One other quick note: the sausage and egg sandwich? that was served for breakfast was absolutely horrible! Thumbs down !"

Pros: "The crew is always great. I liked the environment was cooler. It doesn't need to be refrigerator cold but keeping things on the cooler side is helpful."
Cons: "The boarding process is always horrible. Folks crowd the gate before their class is called. It creates anxiety and edginess. Never a good way to start a trip. While it always goes relatively quickly I feel it should be more organized and folks made to follow a system. Cramming right up against the ticket counter doesn't do anyone any good."

Pros: "I fly Delta Airlines 2x a year and if I had to go on this flight experience alone I would never fly with them again. This particular flight attendant. Brunette who wore all red~ like she had a personal conflict with us from the moment we walked on the plane. We were sitting in the back and could hear the things that she was saying about my grandson and myself. She was rude, snotty, had a sassy mouth. I was COMPLETELY APPALLED as to the way we were treated by her. It was a long flight to have someone you felt was bullying you the whole flight to the moment we were exiting the plane. Karma will come back to her one day..."
Cons: "I fly Delta Airlines 2x a year and if I had to go on this flight experience alone I would never fly with them again. This particular flight attendant. Brunette who wore all red~ like she had a personal conflict with us from the moment we walked on the plane. We were sitting in the back and could hear the things that she was saying about my grandson and myself. She was rude, snotty, had a sassy mouth. I was COMPLETELY APPALLED as to the way we were treated by her. It was a long flight to have someone you felt was bullying you the whole flight to the moment we were exiting the plane. Karma will come back to her one day..."

Cons: "Delta cancelled the flight after midnight on Friday morning, and never rebooked me. I still haven't heard from them. In not even sure why I'm getting alerts about baggage claim."

Pros: "Nothing"
Cons: "No food on a coast to coast flight, outrageous drink prices and a crew that didn't fit in the aisle. Searched at the gate and was sorry I. Am back in America!!!"

Pros: "Friendly staff"
Cons: "Confusing and chaotic boarding procedure"

Pros: "Appreciated the crew keeping things low key as it was a night flight"
Cons: "There were several members of one family on the flight scattered all over the plane. They seemed to want to visit with each other before the flight (making it difficult for me to get to my seat) and during the flight (making it tough to get some sleep). It would be nice if they had been seated together so as not to disturb others. I know this really isn't Delta's fault, but some people aren't very conscientious"

Cons: "no legroom in a first class and expensive seat No entertainment"

Cons: "I felt singled out by the gate agents for this leg of the flight. The gate agent called me out twice - once just to check if my carry on fit into the sample size container. Then she did it again when we were boarding. I know she knew she'd already asked me before. Because afterwards, she tried to play it off, laughing and saying "I'd already asked you, didn't it". My carry on fit with ease. There were people with larger suitcases all around me but she continuously singled me out."

Pros: "I had a middle row seat for this 3 hour 50 minute red eye flight. The plane was quite new. There was plenty of storage space in the bins above the seats. My seat was very comfortable. It reclined a lot. The leg room was more than I needed and I am 6' tall. The individual TV monitor was great. Delta made a long flight quite bearable!"

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "The friendliness and helpfulness of flight attendants was outstanding"

Pros: "very nice airplane"

Pros: "Flight was very good. We look at t.v. and watch movies to make the flight short."
Cons: "I didn't like when I call and ask about the delayed when told that they were waiting on equipment, then when we get to the airport was told that the flight was a international flight that was running late. The Lies!!!!"

Pros: "I loved getting an email with my baggage claim number."
Cons: "The food was the same snack they give in the evening and afternoon, even though it was morning- pretzel, peanuts, or cookies."

Pros: "Short flight"
Cons: "Delayed"

Pros: "we arrived earlier than the time listed"
Cons: "no entertainment"

Pros: "Flight was on time"

Pros: "Flight staff nice"

Pros: "Easy and quick boarding."
Cons: "Should offer free water at least."

Pros: "Crew was friendly and accommodating."
Cons: "?"

Pros: "I paid extra for the added leg room!"

Pros: "I'm never flying them again I like nothing"
Cons: "the flights were never on time"

Pros: "Met expectations"
Cons: "Met expectations"

Pros: "There was nothing outstanding really"
Cons: "It’s a low cost airline, so expectations are very low. Plane was very dirty because it just keeps on hopping back and forth without any cleaning service it seems"

Pros: "I didn’t enjoy anything about this flight unfortunately it was my worst experience with an airline that I’ve ever had."
Cons: "I had checked my bag with was a personal bag and they said it fit inside the metal stand they had so when I proceeded to board another lady had told me I’d pay $50 or wouldn’t get on. She was very rude she let me friend with two bags go on without paying. I took four flights and never had this issue"

Cons: "Check in."

Pros: "Definitely the price. Fairly quick boarding process, just a little congested. Decent priced drinks."
Cons: "Not the most comfortable seats, but there was no one next to me, so it was okay."

Pros: "The crew was courteous and helpful; plane was clean; flight was on time; no problems"

Pros: "Our trip to Knoxville was great- no complaints. A/c cool— flight on time."
Cons: "Trip back to FLL air was not working well. Plane dirty as well."

Cons: "The seats were a bit cramped but I suppose most are these days"

Pros: "Friendly pilot."
Cons: "My reading light kept flashing off and on. So I couldn't read my book."

Pros: "Great crew fast service and flight smooth !"
Cons: "I’m tall and have some back issues I found the seats very close and not too comfortable ! I tried to get A seat by the emergency exit but wasn’t early enough on my pick !"

Cons: "Flight was delayed 6 hours."

Pros: "Getting off the bus!"
Cons: "2.00 for water! Overpriced everything! Crew was not nice. Kindness goes a long way. Not for this crew impatient and just rude to other passengers. We pay good money to ride on the horror bus!"

Pros: "Like the newer plane. The crew was nice."
Cons: "I purchased 2 bulk head seats for more leg room and because they changed the plane, my seats were no longer in the bulk head. We didn't have extra leg room and I would like a refund for the price I paid to upgrade my seats. It is impossible to get service on the phone, since even the customer service number the flight attentendant gave me, still put me on an unbearable hold time. Please refund my money for the seats that you did not provide me with."

Cons: "7.5HR DELAY. LOST A DAY. ARRIVING AT 3AM VS 6:30PM TECH ISSUES NOT ALLOWING CHECKIN ONLINE POORLY TRAINED STAFF AND SUPERIORS AT CHECKIN ONE HR ON TARMAC AS PER HEADCOUNT ISSUE WHEREBY, TWICE ASKED ON PLANE WHO I WAS. EMBARASSING. RUINED MY VACA WITH MY HUSBAND SANS KIDS:-(((((("

Pros: "Standard no frills airline"
Cons: "No room for overhead bags near my seat. I paid $25 to sit up front and $35 for a carry on. I paid extra with the goal of deplaining first. Crew refused to allow me to stow the bags in the front bin, had to place it 10 rows back. If I didn’t run to my gags as soon as Wen landed would have been the last to deplane. If allegiant is going to charge so much for carry on, they need to find a way so front passengers are not squeezed out like this."

Pros: "Great price, flight on time , great trip would use again"

Pros: "Actual flight good and crew very accommodating"
Cons: "Seats poor. Waited 40 mins before the luggage entered the belt for pickup. Held us up for transportation to rent lot."

Pros: "terminal small and easy to navigate"
Cons: "flight was late because of a "valve issue" in terminal, then on the plane pilot tells us its a computer issue and just needed to "reboot" plane computer because it's a computer with wings. Not sure if either of those reasons were true."

Cons: "parking my car 2 weeks in Asheville Long term was $96. I should have gone to Charlotte, parked at my friend's house and paid AA the same rate for a nicer seat and cabin leg room. a la carte pricing ran my bill up even with NO checked luggage. Asheville doesn't have a shuttle service for the long-term parking."

Cons: "baggage staff was super rude. She told me I am the last passenger on the plane which wasn't true. She made me pay $50 because of little overweight. I could easily redistribute the weight among my bags if she gave me little chance. I was a single mom with two kids (3 months and 3 years old) had to pay a fine which I can't afford. Thanks for giving me the chance to express my feelings."

Pros: "Great assistance with a wheelchair to board, and gate crew in CVG is super friendly and helpful."
Cons: "After landing, we spent a hour sitting in the plane, waiting for a gate. After the entire plane had deboarded, it took another 15 minutes for them to bring my husband's wheelchair up from the gate checked storage."

Cons: "I attempted to check in online and was unable to do so. Bad app."

Cons: "It was raining when we landed and we were told the guy didn't want to come out in the rain to open the door so we were stuck on the plane for a while. Being Florida, it rains. If it's your job to pen a plane door, I would think it's reasonable you do it in the rain sometimes. Then up to the passengers on board whether or not they want to get out of the plane when it's raining."

Pros: "Price!"

Pros: "- Good price, even with carry-on and larger seat. - Comfortable seats, despite no incline - better than major airlines."
Cons: "- No food or drinks. - No entertainment. Both are acceptable given the price. - Misinformation regarding flight delay, I was sent notifications and app updated to be 1 hour late. However on arrival, boarding time was as usual."

Pros: "I arrived safely Tommy Destination"
Cons: "It was so hot boarding and unloading. There was no air. Staff was curt and not very friendly as of assistance."

Cons: "Moving from one gate to another. The three hour delay. It appeared that no one person really knew what they were doing. The disabled in wheel chairs we left on there own. One elderly woman literally fell out of her wheel chair to the floor. I was discusseded by the events of the airline."

Pros: "Comfort and speed of the flight. Attentive staff!"
Cons: "Need one craft beer"

Pros: "Nothing. We were scheduled to fly back to Vegas at 7:07 then delayed to 8:30 then 10 pm then 11:25 pm now 1:15 am. This is unbelievable, unacceptable and ridiculous! And I have to work the next day. This is unacceptable! I just received another update that now we're leaving at 1:45 am . Please do not, again do not use Allegheny EVER again!!"
Cons: "So many delays. This airline is unreliable, unprofessional! Ridiculous! Please read my comments above. Do not use Allegiant!"

Pros: "Nothing"
Cons: "I paid for 1A. Was moved because "the crew needed the seat" to the middle. There were SO many open seats. Was unacceptable."

Pros: "On time"
Cons: "Boarding outside in the pouring rain!!!"

Pros: "Cheap"
Cons: "Literally had to pay for every little thing that is usually included in other airline tickets."

Pros: "That fact that they did not suply even one free bottle or cup of water is awful. I was very thirsty but did not get a drink because they chaged $2.00 for one bottle of water, and the is just plain wrong."

Pros: "No Frills Business Travel Good price No hassle Everything on-time and efficient. A choice if I want extras including baggage, seat assignments, etc. Airport convenience"

Pros: "Easy boarding, smooth flight, quick cart service, fast flying"
Cons: "Seats are so small I was window seat with two men who were jammed up so uncomfortably in their seats I felt bad. I was cramped cause they had no choice but to spill over in my seat. I understand safety is important but unless the plane is in middle of taking off or landing, or horrible turbulence anyone should be able to use the bathroom. We had landed and were just sitting and waiting on a gate to open. My fellow travler happened to be on her period n was told No she could not use the bathroom. After the 3rd time of her being sent back I got up with her and a tampon in hand n told the staff they had no choice she was using that bathroom. Of course they had to phone the captain and ask for permission which he ok it, but seriously , what are we supposed to do just sit in our blood. That was not cool."

Pros: "I understand the need to make a profit but comfort is probably the most important aspect of any flight......"
Cons: "Min. 40lbs when others are at 50lbs ..... even 2 free suitcases. I understand the need to make a profit but comfort is probably the most important aspect of any flight......"

Cons: "Arrival in Ft Lauderdale... Bags took an hour to get to carrousel. Never were posted on the information. Flight were, as expected, uncomfortable."

Pros: "Nothing"
Cons: "Everything"

Pros: "Very clean, great staff, smooth flight, easy boarding. All the things you could expect for a great experience. First time flying with this airline so I didn't know what to expect but it was great!"

Pros: "The price and the fact that our flight left late but still arrived almost on time."
Cons: "The gate agent wouldn't switch our seats so we could sit beside each other. We've done this multiple times if we find ourselves not out beside each other and it's never been a problem before. He claimed he had to charge us to do this. We have never been charged before. We fly Allegiant often. The on-board flight crew were so not friendly at all. Typically Allegiant flight attendants aren't as happy as Southwest but they're at least cordial. This crew we're just unhappy, snippy, a little unprofessional (saying huh or what instead of excuse me. Pointing people to things instead of getting it for them or walking them to it) and at one point one stewardess was just rude to a passenger."

Pros: "Staff was wonderful!!"

Pros: "Quick flight."
Cons: "You have to pay extra for everything."

Pros: "The crew was good and had customer service"
Cons: "After an 36 hour delay and only $8 meal voucher in Las Vegas, highly disappointed!!! The next flight was late arrival and Late boarding. everything to include water and sodas are extra fees. not impressed and will never fly Allegiant again"

Pros: "The price range is far for travelers"
Cons: "They should give free snacks and water juice to the customers that travel with this airline. The other airlines off complimentary snacks and drinks other wise it was a good experience"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway to Florida

Airlines flying from Chicago Midway to Florida have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago Midway to Florida

Mandatory masks

Masks required on board, masks provided on flights from Chicago Midway to Florida

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway to Florida

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway to Florida

Book cheap flights from Chicago Midway Airport to Florida

Recent round-trip flight deals

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