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$40 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 8/31. 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
Fri 7/12
Fri 7/19

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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$74
Miami
Miaminonstop$70
Tampa
Tampanonstop$48
Fort Myers
Fort Myers1 stop$145
West Palm Beach
West Palm Beach1 stop$199
Jacksonville
Jacksonville1 stop$262
Sarasota
Sarasota1 stop$284
Pensacola
Pensacola1 stop$145
Key West
Key West1 stop$232
Panama City
Panama City1 stop$196
Valparaiso
Valparaisononstop$134
Daytona Beach
Daytona Beach1 stop$327
Punta Gorda
Punta Gordanonstop$143
Tallahassee
Tallahassee1 stop$428
Gainesville
Gainesville1 stop$322

Good to know

Low season

January

High season

March

Cheapest flight

$40
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 47% 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 - $141 round-trip; Miami $41 one-way - $72 round-trip; Tampa $73 one-way - $96 round-trip
  • Morning departure is around 2% 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

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 10000 reviews
8.6Crew
7.9Comfort
8.0Entertainment
7.4Food
8.2Boarding
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.

Poor response to delay, getting on plane, off plane and back on again

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

The plane was not on time for boarding or departure or arrivals.

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

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

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.

Book cheap flights from Chicago to Florida

Recent round-trip flight deals

9/10Tue
nonstopFrontier
2h 36mMDW-TPA
9/13Fri
nonstopFrontier
2h 43mTPA-MDW
$75
7/10Wed
nonstopFrontier
3h 04mMDW-MIA
7/17Wed
nonstopFrontier
3h 06mMIA-MDW
$76
6/25Tue
nonstopFrontier
2h 39mMDW-TPA
7/2Tue
nonstopFrontier
2h 50mTPA-MDW
$76
8/19Mon
1 stopDelta
4h 21mMDW-PNS
8/24Sat
1 stopDelta
5h 44mPNS-MDW
$176
8/20Tue
1 stopDelta
5h 24mMDW-MCO
8/28Wed
1 stopDelta
4h 23mMCO-MDW
$196
9/9Mon
1 stopAllegiant Air
4h 35mMDW-FLL
9/16Mon
1 stopAllegiant Air
7h 45mFLL-MDW
$223
10/25Fri
1 stopAllegiant Air
13h 21mMDW-FLL
10/28Mon
1 stopAllegiant Air
6h 08mFLL-MDW
$232
7/12Fri
1 stop
14h 37mMDW-FLL
7/14Sun
3 stops
21h 18mFLL-MDW
$383
6/24Mon
1 stop
13h 57mMDW-FLL
6/26Wed
3 stops
23h 50mFLL-MDW
$394
7/11Thu
2 stopsAir Transat
16h 10mMDW-FLL
7/18Thu
2 stopsAir Transat
23h 27mFLL-MDW
$634

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Recent one-way flight deals

8/31Sat
nonstopFrontier
3h 04mMDW-MIA
$40
7/9Tue
nonstopFrontier
2h 38mMDW-TPA
$40
7/10Wed
1 stopDelta
6h 03mMDW-TPA
$98
11/9Sat
1 stopDelta
4h 52mMDW-JAX
$98
8/12Mon
1 stopAllegiant Air
14h 34mMDW-FLL
$100
8/12Mon
1 stopAllegiant Air
14h 34mMDW-FLL
$103
7/1Mon
2 stops
18h 02mMDW-TPA
$136
6/24Mon
2 stops
25h 14mMDW-MCO
$138
6/19Wed
nonstopSouthwest
2h 55mMDW-FLL
$165
6/19Wed
2 stopsSouthwest
7h 05mMDW-FLL
$196

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Last minute flights from Midway to Florida

Last minute flight, train and bus deals

6/17Mon
multi-stopFrontier
18h 05mMDW-MIA
6/26Wed
nonstopFrontier
3h 11mMIA-MDW
$134
6/17Mon
nonstopFrontier
3h 07mMDW-MIA
6/18Tue
nonstopFrontier
3h 14mMIA-MDW
$146
6/13Thu
multi-stopFrontier
23h 30mMDW-TPA
6/19Wed
nonstopFrontier
2h 48mTPA-MDW
$152
6/14Fri
multi-stopAllegiant Air
4h 30mMDW-MCO
6/17Mon
multi-stopAllegiant Air
7h 31mMCO-MDW
$340
6/14Fri
multi-stopAllegiant Air
4h 30mMDW-MCO
6/21Fri
multi-stopAllegiant Air
7h 31mMCO-MDW
$346
6/17Mon
multi-stop
25h 14mMDW-MCO
6/24Mon
multi-stop
7h 31mMCO-MDW
$351
6/17Mon
multi-stop
4h 30mMDW-MCO
6/20Thu
multi-stop
32h 17mMCO-MDW
$356
6/14Fri
multi-stopAvelo Airlines
15h 50mMDW-MCO
6/17Mon
multi-stopAvelo Airlines
10h 45mMCO-MDW
$394
6/14Fri
multi-stopDelta
4h 55mMDW-PBI
6/15Sat
multi-stopDelta
6h 55mPBI-MDW
$448
6/17Mon
multi-stopDelta
7h 50mMDW-RSW
6/25Tue
multi-stopDelta
5h 13mRSW-MDW
$487

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