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Find cheap flights from Chicago Midway Airport to Florida Keys from $30

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 Keys departing on 6/5. 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 6/21
Fri 6/28

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Best Florida Keys Flight Deals

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

Miami
Miaminonstop$39
Key West
Key West1 stop$216

Good to know

Low season

August

High season

March

Cheapest flight

$30
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Florida Keys?

    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 Keys.

  • 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 Keys?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Florida Keys 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 Keys?

    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 Keys 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 Keys?

    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 Keys 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 Keys

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Miami $31 one-way - $90 round-trip

Top 4 airlines serving from Midway to Florida Keys

 
Need help choosing which airline to fly with from Midway to Florida Keys? 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 10585 reviews
8.2Boarding
7.4Food
7.9Comfort
8.6Crew
8.0Entertainment
Airline reviews

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

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

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.

Boarding super slow with people allowed to linger in aisles

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

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

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.

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 Keys

Recent round-trip flight deals

8/12Mon
nonstopFrontier
3h 04mMDW-MIA
8/21Wed
nonstopFrontier
3h 10mMIA-MDW
$82
6/5Wed
nonstopFrontier
3h 07mMDW-MIA
6/15Sat
nonstopFrontier
3h 14mMIA-MDW
$83
6/6Thu
nonstopFrontier
3h 08mMDW-MIA
6/8Sat
nonstopFrontier
3h 14mMIA-MDW
$85
7/3Wed
nonstopFrontier
3h 07mMDW-MIA
7/4Thu
nonstopFrontier
3h 16mMIA-MDW
$86
6/3Mon
nonstopFrontier
3h 11mMDW-MIA
6/15Sat
nonstopFrontier
3h 14mMIA-MDW
$87
6/10Mon
nonstopFrontier
3h 07mMDW-MIA
6/20Thu
nonstopFrontier
3h 16mMIA-MDW
$89
7/4Thu
nonstopFrontier
3h 08mMDW-MIA
7/13Sat
nonstopFrontier
3h 06mMIA-MDW
$91
6/3Mon
nonstopFrontier
3h 11mMDW-MIA
6/18Tue
nonstopFrontier
3h 14mMIA-MDW
$92
8/10Sat
1 stopDelta
5h 58mMDW-EYW
8/17Sat
1 stopDelta
4h 42mEYW-MDW
$216
9/9Mon
1 stopDelta
6h 26mMDW-MIA
9/12Thu
1 stopDelta
6h 32mMIA-MDW
$216

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Recent one-way flight deals

6/5Wed
nonstopFrontier
3h 07mMDW-MIA
$30
6/3Mon
nonstopFrontier
3h 11mMDW-MIA
$31
6/24Mon
nonstopFrontier
3h 07mMDW-MIA
$32
6/23Sun
nonstopFrontier
3h 08mMDW-MIA
$37
7/9Tue
1 stopDelta
5h 06mMDW-MIA
$108
8/13Tue
1 stopDelta
4h 56mMDW-MIA
$109
7/15Mon
nonstopSouthwest
3h 00mMDW-MIA
$153
6/7Fri
2 stops
7h 21mMDW-MIA
$157
6/7Fri
2 stops
22h 22mMDW-MIA
$223
8/17Sat
2 stopsVolaris
17h 29mMDW-MIA
$395

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Last minute flights from Midway to Florida Keys

Last minute flight, train and bus deals

5/27Mon
nonstopFrontier
3h 11mMDW-MIA
5/29Wed
nonstopFrontier
3h 15mMIA-MDW
$156
5/27Mon
nonstopFrontier
3h 11mMDW-MIA
5/29Wed
nonstopFrontier
3h 15mMIA-MDW
$167
5/27Mon
nonstopFrontier
3h 11mMDW-MIA
5/31Fri
nonstopFrontier
3h 15mMIA-MDW
$199
5/27Mon
nonstopUndisclosed Carrier
2h 55mMDW-MIA
5/30Thu
nonstopUndisclosed Carrier
3h 20mMIA-MDW
$426
5/26Sun
multi-stopDelta
5h 08mMDW-MIA
5/29Wed
multi-stopDelta
8h 35mMIA-MDW
$471
5/26Sun
multi-stopDelta
5h 54mMDW-MIA
6/8Sat
multi-stopDelta
5h 48mMIA-MDW
$522
5/24Fri
multi-stop
26h 19mMDW-MIA
5/27Mon
multi-stop
32h 50mMIA-MDW
$690
5/24Fri
multi-stop
26h 19mMDW-MIA
5/30Thu
multi-stop
17h 51mMIA-MDW
$736
5/24Fri
multi-stopVolaris
16h 10mMDW-MIA
5/28Tue
multi-stopVolaris
19h 17mMIA-MDW
$1,123
5/24Fri
multi-stopVolaris
16h 10mMDW-MIA
5/30Thu
multi-stopVolaris
17h 51mMIA-MDW
$1,205

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Chicago Midway Airport - Florida Keys Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Florida Keys - Chicago Midway Airport

Cabin classes:

$650
$728
$477
$27