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Find cheap flights from Chicago Midway Airport to Florida from $44

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 7/15. 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
0 bags
Thu 6/27
Thu 7/4

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Best Florida Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Orlando
Orlandononstop$98
Miami
Miaminonstop$36
Fort Lauderdale
Fort Lauderdale1 stop$100
Tampa
Tampanonstop$81
Fort Myers
Fort Myers1 stop$156
West Palm Beach
West Palm Beach1 stop$222
Jacksonville
Jacksonville1 stop$157
Sarasota
Sarasota1 stop$142
Pensacola
Pensacola1 stop$159
Key West
Key West1 stop$303
Panama City
Panama City1 stop$256
Valparaiso
Valparaisononstop$129
Daytona Beach
Daytona Beach1 stop$359
Punta Gorda
Punta Gordanonstop$173
Tallahassee
Tallahassee1 stop$498
Gainesville
Gainesville1 stop$404

Good to know

Low season

January

High season

March

Cheapest flight

$44
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 48% 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 to Florida from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to 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 to Florida with an airline and back to Chicago Midway Airport 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 to Florida from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $77 one-way - $151 round-trip; Miami $34 one-way - $86 round-trip; Tampa $50 one-way - $91 round-trip
  • Morning departure is around 7% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Florida

 
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
DeltaOverall score based on 10502 reviews
7.4Food
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

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

2.0 MediocreNairan, May 2024JFK - FLL
Read more about Delta reviews

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

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

Everything was really good but the seats are not very comfortable.

Spirit canceled the flight in March and never notified me!

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

There was no wifi, there was no usb charger on the planes Frontier lowered the weight limit on suitcases from 50 to 40 pounds Frontier now charges for a seat...really? If i don't pay for a basic seat, do i stand the whole flight? Frontier now charges for the carry on, just like for the checked suitcase The bundle pricing is way over priced.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Book cheap flights from Chicago to Florida

Recent round-trip flight deals

6/10Mon
nonstopFrontier
3h 07mMDW-MIA
6/14Fri
nonstopFrontier
3h 11mMIA-MDW
$73
6/23Sun
nonstopFrontier
3h 08mMDW-MIA
6/26Wed
nonstopFrontier
3h 11mMIA-MDW
$74
6/17Mon
nonstopFrontier
3h 07mMDW-MIA
6/21Fri
nonstopFrontier
3h 11mMIA-MDW
$75
6/11Tue
nonstop
3h 08mMDW-MIA
6/12Wed
1 stop
12h 56mMIA-MDW
$83
6/15Sat
nonstop
3h 06mMDW-MIA
6/19Wed
1 stop
12h 56mMIA-MDW
$145
7/5Fri
1 stopDelta
4h 22mMDW-PNS
7/10Wed
1 stopDelta
4h 03mPNS-MDW
$208
8/13Tue
1 stopDelta
6h 06mMDW-RSW
8/17Sat
1 stopDelta
5h 55mRSW-MDW
$216
6/10Mon
1 stopAllegiant Air
4h 30mMDW-MCO
6/17Mon
1 stopAllegiant Air
7h 31mMCO-MDW
$235
6/7Fri
1 stopAllegiant Air
4h 30mMDW-MCO
6/10Mon
1 stopAllegiant Air
6h 57mMCO-MDW
$240
6/11Tue
nonstopSouthwest
2h 30mMDW-MCO
6/15Sat
nonstopSouthwest
2h 45mMCO-MDW
$288

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Recent one-way flight deals

7/15Mon
nonstopFrontier
3h 04mMDW-MIA
$44
7/27Sat
nonstopFrontier
3h 04mMDW-MIA
$45
7/31Wed
nonstopFrontier
3h 04mMDW-MIA
$46
7/9Tue
1 stopDelta
6h 41mMDW-TPA
$98
7/23Tue
1 stopDelta
6h 13mMDW-MCO
$98
7/5Fri
1 stopAllegiant Air
4h 30mMDW-MCO
$105
6/7Fri
1 stopAllegiant Air
4h 30mMDW-MCO
$111
6/10Mon
2 stops
20h 25mMDW-PNS
$131
6/10Mon
2 stops
25h 48mMDW-MCO
$140
6/21Fri
1 stopAvelo Airlines
14h 00mMDW-RSW
$246

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Last minute flights from Midway to Florida

Last minute flight, train and bus deals

6/2Sun
nonstopFrontier
2h 42mMDW-TPA
6/9Sun
nonstopFrontier
2h 46mTPA-MDW
$130
6/2Sun
nonstopFrontier
2h 42mMDW-TPA
6/5Wed
nonstopFrontier
2h 48mTPA-MDW
$150
5/31Fri
multi-stopAllegiant Air
5h 00mMDW-MCO
6/3Mon
multi-stopAllegiant Air
6h 53mMCO-MDW
$280
5/31Fri
multi-stopAllegiant Air
5h 00mMDW-MCO
6/3Mon
multi-stopAllegiant Air
6h 53mMCO-MDW
$300
6/1Sat
multi-stopDelta
4h 46mMDW-FLL
6/4Tue
multi-stopDelta
6h 28mFLL-MDW
$327
6/1Sat
multi-stop
24h 22mMDW-FLL
6/3Mon
multi-stop
8h 12mFLL-MDW
$353
5/30Thu
multi-stopDelta
4h 54mMDW-PNS
6/2Sun
multi-stopDelta
4h 04mPNS-MDW
$378
5/30Thu
multi-stop
25h 16mMDW-MCO
6/3Mon
multi-stop
6h 53mMCO-MDW
$415
5/29Wed
nonstopSouthwest
2h 35mMDW-MCO
5/30Thu
nonstopSouthwest
2h 50mMCO-MDW
$497
5/29Wed
nonstopSouthwest
2h 35mMDW-MCO
5/30Thu
multi-stopSouthwest
4h 50mMCO-MDW
$501

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