$39 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 2/3. 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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Search hundreds of travel sites at once for deals on flights to Florida Keys

 
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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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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$237

Good to know

Low season

August

High season

March

Cheapest flight

$39
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 19% 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 $94 one-way - $166 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 January.

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 4671 reviews
8.1Comfort
8.7Crew
7.2Food
8.2Boarding
7.7Entertainment
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.

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.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

The ticket agent wouldn't check our bags, eventhough the flight was delayed and wouldn't board for another hour. The gate agents were only mildly better than the ticket agent. They also had a terrible attitude and work ethics.

we are al people and we go through stuff so my scale is only how i felt, I understand we are all humans, i would definitely ride with soirit again, people in orlando are very helpful which makes it all the better .

My flight was arbitrarily changed from 6:00 AM to 5:10 AM ... One less hour of sleep after Christmas Eve, NOT very thoughtful, Oh, and I could not get a refund!!! I paid extra for a front seat and WIFI, there's was NO WIFI (flight 993 Dec 25). Why do you call what you offer FOOD? Would you feed your kids this stuff when you are trapped inside a steel tube for Hours??? Will I get a refund?

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Try bad experience. The flight took off leaving behind everyone’s baggage and to top it off the captain nor the crew bothered letting anyone know about this and instead asked us that the baggage can be claimed from carousel 13 when the flight didn’t have even a single baggage. Furthermore they let everyone stand around the carousel for 1 hour to finally let people know that no baggage were loaded onto the flight.

Lost MacBook, had time to retrieve, but was told I had no time. Need Silver MacBook back

I did not fly Spirit. Connie fraudulently used my email to book her flight. I do not know Connie!

Terrible all around. Not much else to say, other than an awful experience from start to finish.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

The MOST uncomfortable seat I've EVER experienced on ANY airlines. My wife & I were in agony at the end of the flight. NEVER AGAIN!

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.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

Horrible my trip was delayed 3 hours, we already have set in the plane and they delayed the flight.

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.
2/10man.
nonstopFrontier
3h 12mMDW-MIA
2/15lør.
nonstopFrontier
3h 23mMIA-MDW
$82
2/2søn.
nonstopFrontier
3h 12mMDW-MIA
2/15lør.
nonstopFrontier
3h 23mMIA-MDW
$83
2/12ons.
nonstopFrontier
3h 12mMDW-MIA
2/15lør.
nonstopFrontier
3h 23mMIA-MDW
$86
2/12ons.
nonstopFrontier
3h 12mMDW-MIA
2/19ons.
nonstopFrontier
3h 31mMIA-MDW
$87
2/4tir.
nonstopSouthwest
3h 00mMDW-MIA
2/11tir.
nonstopSouthwest
3h 15mMIA-MDW
$157
1/27man.
nonstopSouthwest
3h 00mMDW-MIA
1/28tir.
nonstopSouthwest
3h 15mMIA-MDW
$197
2/11tir.
nonstopSouthwest
3h 00mMDW-MIA
2/18tir.
nonstopSouthwest
3h 20mMIA-MDW
$207
2/4tir.
1 stopDelta
5h 08mMDW-MIA
2/6tor.
1 stopDelta
6h 52mMIA-MDW
$217
2/18tir.
1 stopDelta
4h 38mMDW-EYW
2/19ons.
1 stopDelta
5h 06mEYW-MDW
$237
1/28tir.
1 stopDelta
5h 24mMDW-EYW
2/4tir.
1 stopDelta
5h 04mEYW-MDW
$249

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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.
2/3man.
nonstopFrontier
3h 12mMDW-MIA
$39
3/1lør.
nonstopFrontier
3h 08mMDW-MIA
$44
2/19ons.
nonstopFrontier
3h 12mMDW-MIA
$48
2/22lør.
nonstopFrontier
3h 08mMDW-MIA
$49
2/5ons.
nonstopSouthwest
3h 00mMDW-MIA
$79
3/12ons.
nonstopSouthwest
3h 00mMDW-MIA
$99
2/19ons.
1 stopDelta
5h 03mMDW-MIA
$109
1/20man.
1 stop
9h 00mMDW-EYW
$161
1/13man.
1 stop
9h 00mMDW-EYW
$166
3/29lør.
1 stopDelta
7h 45mMDW-MIA
$177

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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.
1/10fre.
nonstopFrontier
3h 13mMDW-MIA
1/17fre.
nonstopFrontier
3h 29mMIA-MDW
$181
1/10fre.
nonstopFrontier
3h 13mMDW-MIA
1/16tor.
nonstopFrontier
3h 31mMIA-MDW
$193
1/10fre.
nonstopFrontier
3h 13mMDW-MIA
1/17fre.
multi-stopFrontier
19h 34mMIA-MDW
$197
1/10fre.
nonstopFrontier
3h 13mMDW-MIA
2/10man.
multi-stopFrontier
9h 13mMIA-MDW
$206
1/6man.
multi-stop
8h 26mMDW-MIA
1/8ons.
multi-stop
50h 05mMIA-MDW
$443
1/10fre.
multi-stopSouthwest
10h 20mMDW-MIA
1/12søn.
multi-stopSouthwest
7h 40mMIA-MDW
$502
1/7tir.
multi-stopDelta
4h 38mMDW-EYW
1/14tir.
multi-stopDelta
4h 48mEYW-MDW
$519
1/10fre.
nonstopSouthwest
3h 00mMDW-MIA
1/25lør.
nonstopSouthwest
3h 10mMIA-MDW
$537
1/7tir.
multi-stopDelta
5h 29mMDW-MIA
1/12søn.
multi-stopDelta
6h 08mMIA-MDW
$758
1/7tir.
multi-stop
22h 14mMDW-MIA
1/13man.
multi-stop
16h 17mMIA-MDW
$803

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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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