$37 Find Cheap Flights from Chicago Midway Airport to Florida Keys

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 4/15. 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.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida Keys, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida Keys, as well as popular online travel agencies
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Best Florida Keys Flight Deals from Midway

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

Miami
Miaminonstop$77
Key West
Key West1 stop$269

Good to know

Low season

November

High season

March

Cheapest flight

$37
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 3% lower on average.
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 from Chicago Midway Airport to Florida Keys 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 from Chicago Midway Airport to Florida Keys with an airline and back 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 from Chicago Midway Airport to Florida Keys 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 $66 one-way - $108 round-trip
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be April, May and June. The cheapest month to fly from Chicago is April.

Top 5 airlines serving from Midway to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Florida Keys. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
8.1
SouthwestOverall score based on 4396 reviews
8.7Crew
7.1Food
8.2Boarding
8.1Comfort
7.6Entertainment
Airline reviews

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

10.0 ExcellentKeith, Jan 2025IND - MCO
Read more Southwest reviews

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

wifi wasn't working correctly so couldn't watch live tv

Flight was delayed by 12 minutes. Boarding wasn’t fun. The crew was nice though.

The flight was promptly on schedule and Southwest delivered everything they promised. No excuses for any shortfalls just 100% ownership of their responsibilities and business. The boarding and seating policy is a complete shambles. What started out as a great idea when Southwest first hit the market has been turned into a disaster due to the lack of integrity in many of the people who fly Southwest and take advantage of Southwest generosity at the expense of their fellow passengers.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

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.

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Flight was on time It was a good flight overall

The senior flight attendant was engaging, funny and made everyone feel at ease. She is an asset to your team.

Needs legroom for tall people. Needs to offer a glass of water.

They changed our departure time 6 times before I even reached the airport. Delayed, Ontime, Delayed Back on time, Then Delayed. We finally boarded the plane and then we had to sit on the runway for over an hour only to be told they were taking us back to the gate for an additional 2 hour delay. Lack of communication and a complete waste of time! Never again!

I was traveling with my son and it was our first time with spirit so I didn’t realize our seats weren’t assigned. They scrambled and gave us seats next to each other. Also My son got sick on the plane and they really took care of him. Super family friendly crew and experience!

Great. I didn't eat or drink anything, nor did I have an option to be entertained, so i answered "okay"... but those categoriesreally don't apply. Everything else was great.

More groups for smother boarding, I didnt have any food. and there was no entertainment

Not bad but I was told that I got a 1 carry. When I got to the gate I was told my purse was considered my carry on. I had never been told that before.

The flights were on time, the schedule was convenient for me, without delays.

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

Boarding was organized and flight was on time. Overall very satisfied with my flight.

The boarding gate was in Terminal D, but the Frontier counter was in Terminal E. So I had to move back and forth between terminals to check in my luggage. This was the worst experience that I had in terms of flights.

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Airline changed the gate from Terminal A to Terminal D which is quite far and only sent a text message few minutes before boarding. Around 50 people missed their flight and as plane didn’t wait for them.

The personal at boarding are rude and try to steel people with their rule of personal item , really bad experience for us

I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.

Book cheap flights from Chicago to Florida Keys

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Chicago to Florida Keys found on KAYAK in the last 72 hours.
4/15Tue
nonstopFrontier
3h 08mMDW-MIA
4/17Thu
nonstopFrontier
3h 26mMIA-MDW
$91
4/3Thu
nonstopFrontier
3h 08mMDW-MIA
4/8Tue
nonstopFrontier
3h 28mMIA-MDW
$96
3/21Fri
1 stop
7h 30mMDW-MIA
3/25Tue
nonstop
3h 31mMIA-MDW
$189
3/31Mon
nonstopSouthwest
3h 00mMDW-MIA
4/2Wed
nonstopSouthwest
3h 15mMIA-MDW
$208
4/1Tue
1 stopDelta
5h 26mMDW-MIA
4/8Tue
1 stopDelta
6h 47mMIA-MDW
$217
3/15Sat
1 stopDelta
7h 09mMDW-MIA
3/18Tue
1 stopDelta
5h 31mMIA-MDW
$219
3/12Wed
1 stopSouthwest
6h 15mMDW-MIA
3/18Tue
nonstopSouthwest
3h 20mMIA-MDW
$228
4/20Sun
1 stop
11h 00mMDW-EYW
4/24Thu
1 stop
13h 26mEYW-MDW
$374
7/3Thu
2 stopsAllegiant Air
27h 59mMDW-EYW
7/6Sun
1 stopAllegiant Air
18h 21mEYW-MDW
$429
7/3Thu
2 stopsAllegiant Air
27h 59mMDW-EYW
7/6Sun
2 stopsAllegiant Air
25h 47mEYW-MDW
$487

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Florida Keys found on KAYAK in the last 72 hours.
4/15Tue
nonstopFrontier
3h 08mMDW-MIA
$37
4/15Tue
nonstopFrontier
3h 08mMDW-MIA
$39
4/1Tue
nonstopFrontier
3h 08mMDW-MIA
$40
4/23Wed
nonstopSouthwest
2h 55mMDW-MIA
$90
4/22Tue
nonstopSouthwest
2h 55mMDW-MIA
$99
3/25Tue
1 stopDelta
5h 26mMDW-MIA
$109
3/18Tue
1 stopDelta
5h 26mMDW-MIA
$110
3/21Fri
1 stop
7h 30mMDW-MIA
$149
4/13Sun
3 stops
42h 06mMDW-MIA
$151
3/11Tue
2 stopsSpirit Airlines
12h 47mMDW-MIA
$176

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Last minute flights from Midway to Florida Keys

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Florida Keys that are departing in the next 10 days.
2/27Thu
nonstopFrontier
3h 12mMDW-MIA
3/5Wed
nonstopFrontier
3h 31mMIA-MDW
$178
2/25Tue
nonstopFrontier
3h 12mMDW-MIA
3/1Sat
nonstopFrontier
3h 28mMIA-MDW
$236
2/24Mon
nonstopFrontier
3h 08mMDW-MIA
2/28Fri
nonstopFrontier
3h 28mMIA-MDW
$246
2/24Mon
nonstopFrontier
3h 08mMDW-MIA
3/1Sat
nonstopFrontier
3h 23mMIA-MDW
$248
2/26Wed
nonstopFrontier
3h 12mMDW-MIA
2/28Fri
nonstopFrontier
3h 28mMIA-MDW
$249
2/24Mon
multi-stopDelta
6h 27mMDW-EYW
2/26Wed
multi-stopDelta
5h 06mEYW-MDW
$416
2/27Thu
multi-stopDelta
6h 46mMDW-MIA
3/5Wed
multi-stopDelta
7h 38mMIA-MDW
$528
2/26Wed
nonstopSouthwest
3h 00mMDW-MIA
3/7Fri
nonstopSouthwest
3h 15mMIA-MDW
$587
2/23Sun
multi-stopSouthwest
6h 00mMDW-MIA
2/27Thu
nonstopSouthwest
3h 20mMIA-MDW
$602
2/27Thu
multi-stopAllegiant Air
21h 43mMDW-EYW
3/3Mon
multi-stopAllegiant Air
32h 42mEYW-MDW
$774

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Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

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