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Find cheap flights from Chicago Midway Airport to Florida from $47

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 5/30. 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
Tue 5/28
Tue 6/4

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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$60
Miami
Miaminonstop$77
Fort Lauderdale
Fort Lauderdale1 stop$124
Tampa
Tampanonstop$55
Fort Myers
Fort Myers1 stop$197
Jacksonville
Jacksonville1 stop$158
Sarasota
Sarasota1 stop$272
Key West
Key West1 stop$248
Pensacola
Pensacola1 stop$167
Panama City
Panama City1 stop$318
Valparaiso
Valparaisononstop$150
Daytona Beach
Daytona Beach1 stop$569
Punta Gorda
Punta Gordanonstop$129
Tallahassee
Tallahassee1 stop$593
Gainesville
Gainesville1 stop$382

Good to know

Low season

August

High season

March

Cheapest flight

$47
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from Chicago Midway Airport to Tampa

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 - $155 round-trip; Miami $54 one-way - $84 round-trip; Tampa $64 one-way - $104 round-trip
  • Morning departure is around 3% 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 10932 reviews
7.4food
8.6crew
7.9comfort
8.0entertainment
8.2boarding
Airline reviews

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!

4.0 OkayAndrew, Apr 2024RDU - MCO
Read more about Delta reviews

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.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

First time travel in economy and the worst experience I ever had ! Shame on paying 600 dollars to be in a tuna can ! Service was terrible no even water no even class no even matters your flight attendants were lazy and sloppy very bad experience! After all these years traveling in first and once I try this cause I need to go to a destination for an emergency wow shame on you !

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

The weight limit per bag was really low - 40 lbs - so we had to pay extra. Then, they said their carry on size was 14x18x8, and we measured our bag very carefully. It was within the limit, yet they said it was too big, so we ended up paying an extra $100 for that too!! So it wasn’t the cheap flight we thought it would be. Then, they moved up our initial flight to depart 3 hours earlier which meant we had to be out on the road by 7 am and then have a 6 hour layover and we got home at 2am. It was a grueling day. I won’t be flying with them again.

Overall it was a good experience. Stewards were very kind and professional. The departure and arrival times were as promised. Plane was clean.

Terrible as usual!!!! Very unprofessional and rude flight attendants! You get what you pay for! HORRIBLE

My experience was above excellent!!!! First the lady that pushed me in the wheelchair to the gate was outstanding!!! Then the ladies at the gate went over and beyond, by helping me fill out the immigration form! I would not have been able to get to Guatemala without their help!!! God bless them all! They were amazing 🙏❤️🙏

First....my trip was from Ft. Myers to Philly (not the other way around). Plane was clean, staff was friendly and flight was efficient with boarding and flight time. Thumbs up all around.

Early departure and arrival. Cabin very cold. Waited a while for luggage to come out

The no frills ticket price. The seats are very uncomfortable.

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.

Bought seats on the flight and they were supposed to be 2 and a jumpseat. Plane clearly changed and it was a regular 3 seat row. Asked for a refund and was denied. If I wanted to sit next to someone else I wouldn't have bought the seats..

Flying frontier reminded me of flying with my family in the 80’s in all of the worst ways possible. From poor customer service to little to no technology. The plane was dirty old and also stuck in the 80’s. From their seatbelts to not having anywhere to charge our phones the seats and the equipment I wasn’t sure if I was being punked or thrown back in time. Needless to say I don’t see myself flying frontier ever again.

Book cheap flights from Chicago to Florida

Recent round-trip flight deals

5/14Tue
nonstopFrontier
2h 46mMDW-TPA
5/23Thu
nonstopFrontier
2h 47mTPA-MDW
$76
5/11Sat
nonstopFrontier
3h 00mMDW-MCO
5/18Sat
nonstopFrontier
2h 58mMCO-MDW
$76
5/22Wed
nonstopFrontier
3h 11mMDW-MIA
5/31Fri
nonstopFrontier
3h 15mMIA-MDW
$77
5/29Wed
nonstopFrontier
3h 11mMDW-MIA
6/3Mon
nonstopFrontier
3h 15mMIA-MDW
$78
6/1Sat
1 stop
10h 40mMDW-FLL
6/3Mon
1 stop
13h 31mFLL-MDW
$185
5/29Wed
1 stopDelta
7h 09mMDW-TPA
6/1Sat
1 stopDelta
5h 02mTPA-MDW
$196
8/24Sat
1 stopDelta
4h 46mMDW-MCO
8/27Tue
1 stopDelta
7h 06mMCO-MDW
$198
6/1Sat
1 stop
10h 40mMDW-FLL
6/3Mon
1 stop
10h 41mFLL-MDW
$221
5/27Mon
nonstopSouthwest
2h 35mMDW-TPA
5/30Thu
nonstopSouthwest
2h 40mTPA-MDW
$240
5/22Wed
2 stopsWestJet
19h 25mMDW-RSW
5/25Sat
2 stopsWestJet
15h 42mRSW-MDW
$1,205

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Recent one-way flight deals

5/30Thu
nonstopFrontier
2h 42mMDW-TPA
$47
5/27Mon
nonstopFrontier
3h 11mMDW-MIA
$48
5/17Fri
1 stop
9h 11mMDW-FLL
$97
5/28Tue
1 stopDelta
7h 12mMDW-TPA
$98
5/28Tue
1 stopDelta
5h 02mMDW-MCO
$98
5/26Sun
1 stop
12h 36mMDW-FLL
$148
5/4Sat
2 stopsSpirit Airlines
13h 16mMDW-MIA
$187
5/4Sat
3 stopsSpirit Airlines
16h 20mMDW-MIA
$199
6/8Sat
2 stopsPorter Airlines
10h 44mMDW-MCO
$246
5/12Sun
2 stopsPorter Airlines
10h 04mMDW-MCO
$277

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Last minute flights from Midway to Florida

Last minute flight, train and bus deals

5/1Wed
nonstopFrontier
3h 17mMDW-MIA
5/8Wed
nonstopFrontier
3h 32mMIA-MDW
$119
5/3Fri
nonstopFrontier
3h 17mMDW-MIA
5/8Wed
nonstopFrontier
3h 32mMIA-MDW
$123
4/30Tue
nonstopFrontier
3h 17mMDW-MIA
5/7Tue
nonstopFrontier
3h 32mMIA-MDW
$131
4/30Tue
multi-stopDelta
5h 38mMDW-FLL
5/7Tue
multi-stopDelta
4h 46mFLL-MDW
$322
5/1Wed
multi-stopDelta
5h 03mMDW-PBI
6/1Sat
multi-stopDelta
6h 01mPBI-MDW
$322
5/2Thu
nonstopSouthwest
2h 30mMDW-TPA
5/10Fri
nonstopSouthwest
2h 40mTPA-MDW
$397
5/2Thu
multi-stopSouthwest
4h 00mMDW-TPA
5/10Fri
nonstopSouthwest
2h 40mTPA-MDW
$401
5/1Wed
multi-stop
33h 43mMDW-TPA
5/4Sat
multi-stop
6h 51mTPA-MDW
$488
4/30Tue
multi-stop
19h 10mMDW-FLL
5/3Fri
multi-stop
22h 47mFLL-MDW
$1,010
4/29Mon
multi-stopVolaris
16h 10mMDW-MIA
5/1Wed
multi-stopVolaris
17h 51mMIA-MDW
$1,071

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