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Find cheap flights from Chicago Midway Airport to Florida from $39

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 8/6. 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 6/7
Fri 6/14

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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$57
Miami
Miaminonstop$37
Tampa
Tampanonstop$58
Fort Myers
Fort Myers1 stop$133
Jacksonville
Jacksonville1 stop$158
Sarasota
Sarasota1 stop$264
Pensacola
Pensacola1 stop$208
Key West
Key West1 stop$226
Panama City
Panama City2 stops$302
Valparaiso
Valparaisononstop$117
Punta Gorda
Punta Gordanonstop$142
Tallahassee
Tallahassee1 stop$443
Gainesville
Gainesville1 stop$332

Good to know

Low season

January

High season

March

Cheapest flight

$39
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 52% 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 $65 one-way - $137 round-trip; Miami $42 one-way - $83 round-trip; Tampa $49 one-way - $93 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 10789 reviews
7.9Comfort
8.0Entertainment
8.6Crew
7.4Food
8.2Boarding
Airline reviews

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.

10.0 ExcellentDonnel, Apr 2024ATL - EYW
Read more about Delta reviews

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.

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.

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

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.

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.

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..

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
5/30Thu
nonstopFrontier
2h 42mMDW-TPA
6/4Tue
nonstopFrontier
2h 47mTPA-MDW
$73
5/31Fri
nonstopFrontier
3h 11mMDW-MIA
6/5Wed
nonstopFrontier
3h 11mMIA-MDW
$74
7/16Tue
nonstopFrontier
2h 36mMDW-TPA
7/24Wed
nonstopFrontier
2h 43mTPA-MDW
$74
5/30Thu
1 stopDelta
5h 06mMDW-TPA
6/4Tue
1 stopDelta
6h 02mTPA-MDW
$202
5/21Tue
1 stopDelta
5h 02mMDW-MCO
5/26Sun
1 stopDelta
4h 56mMCO-MDW
$202
5/31Fri
1 stopAllegiant Air
5h 00mMDW-MCO
6/3Mon
1 stopAllegiant Air
6h 53mMCO-MDW
$225
5/20Mon
1 stop
10h 33mMDW-FLL
6/3Mon
2 stops
12h 23mFLL-MDW
$281
6/7Fri
1 stop
5h 27mMDW-FLL
6/14Fri
1 stop
8h 25mFLL-MDW
$305
5/20Mon
1 stopAllegiant Air
10h 33mMDW-FLL
5/24Fri
1 stopAllegiant Air
5h 56mFLL-MDW
$340

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Recent one-way flight deals

8/6Tue
nonstopFrontier
2h 36mMDW-TPA
$39
5/26Sun
nonstopFrontier
2h 42mMDW-TPA
$40
6/5Wed
nonstopFrontier
3h 07mMDW-MIA
$41
5/15Wed
1 stop
11h 21mMDW-FLL
$43
5/22Wed
1 stop
6h 57mMDW-FLL
$48
6/5Wed
1 stopDelta
5h 33mMDW-TPA
$98
5/30Thu
1 stopDelta
5h 23mMDW-MCO
$98
6/17Mon
1 stopAllegiant Air
13h 57mMDW-FLL
$103
6/7Fri
1 stopAllegiant Air
4h 30mMDW-MCO
$105
8/4Sun
1 stopSouthwest
6h 25mMDW-FLL
$163

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Last minute flights from Midway to Florida

Last minute flight, train and bus deals

5/13Mon
nonstopFrontier
2h 56mMDW-MCO
5/18Sat
nonstopFrontier
2h 58mMCO-MDW
$136
5/11Sat
nonstopFrontier
3h 00mMDW-MCO
5/18Sat
nonstopFrontier
2h 58mMCO-MDW
$138
5/11Sat
multi-stopDelta
4h 57mMDW-MCO
5/15Wed
multi-stopDelta
5h 41mMCO-MDW
$262
5/11Sat
multi-stopDelta
4h 57mMDW-MCO
5/14Tue
multi-stopDelta
7h 10mMCO-MDW
$307
5/13Mon
multi-stopAllegiant Air
21h 57mMDW-FLL
5/24Fri
multi-stopAllegiant Air
5h 56mFLL-MDW
$401
5/10Fri
multi-stopAllegiant Air
19h 28mMDW-FLL
5/13Mon
multi-stopAllegiant Air
6h 52mFLL-MDW
$428
5/13Mon
multi-stop
24h 33mMDW-MCO
5/19Sun
multi-stop
24h 14mMCO-MDW
$476
5/13Mon
multi-stop
16h 05mMDW-MCO
5/19Sun
multi-stop
24h 14mMCO-MDW
$478
5/11Sat
multi-stopVolaris
17h 29mMDW-MIA
5/18Sat
multi-stopVolaris
19h 12mMIA-MDW
$892
5/13Mon
multi-stopVolaris
18h 39mMDW-MCO
5/19Sun
multi-stopVolaris
19h 28mMCO-MDW
$974

Search by stops

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