$63 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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KAYAK searches 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
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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$141
Key West
Key West1 stop$269

Cheap Flight Deals from Midway to Florida Keys (MDW-zzEOA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Florida Keys that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Florida Keys

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Florida Keys.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Frontier Logo
2:16 pm - 6:22 pmMDW-MIA
3h 06mnonstop
Frontier Logo
11:03 am - 1:31 pmMIA-MDW
3h 28mnonstop
$141Frontier
Find Deal
Sun, Apr 13 - Tue, Apr 15
Frontier Logo
2:16 pm - 6:22 pmMDW-MIA
3h 06mnonstop
Frontier Logo
12:25 pm - 3:00 pmMIA-MDW
3h 35mnonstop
$162Frontier
Find Deal
Sun, Apr 13 - Sat, Apr 19
Frontier Logo
8:00 am - 12:08 pmMDW-MIA
3h 08mnonstop
Frontier Logo
12:25 pm - 3:00 pmMIA-MDW
3h 35mnonstop
$167Frontier
Find Deal
Thu, Apr 17 - Sat, Apr 19
Southwest Logo
5:10 pm - 9:05 pmMDW-MIA
2h 55mnonstop
Southwest Logo
7:00 am - 9:10 amMIA-MDW
3h 10mnonstop
$177Southwest
Find Deal
Wed, May 14 - Thu, May 15
Southwest Logo
5:10 pm - 9:05 pmMDW-MIA
2h 55mnonstop
Southwest Logo
7:00 am - 9:10 amMIA-MDW
3h 10mnonstop
$178Southwest
Find Deal
Wed, Apr 30 - Wed, May 7
Delta Logo
5:25 pm - 11:46 pmMDW-MIA
5h 21m1 stop
Delta Logo
8:40 am - 12:28 pmMIA-MDW
4h 48m1 stop
$217Delta
Find Deal
Sat, May 17 - Sat, May 24
Delta Logo
9:52 am - 4:57 pmMDW-MIA
6h 05m1 stop
Delta Logo
8:55 am - 2:48 pmMIA-MDW
6h 53m1 stop
$218Delta
Find Deal
Sat, Apr 26 - Sat, May 3
Allegiant Air Logo
8:36 pm - 3:03 pmMDW-EYW
17h 27m2 stops
Allegiant Air Logo
8:53 am - 2:03 pmEYW-MDW
30h 10m2 stops
$351Allegiant Air
Find Deal
Fri, Jun 6 - Sun, Jun 8
 Logo
12:58 pm - 7:53 amMDW-MIA
17h 55m2 stops
 Logo
7:17 pm - 9:49 pmMIA-MDW
3h 32mnonstop
Sat, Apr 19 - Sun, Apr 20
 Logo
4:01 pm - 8:00 amMDW-EYW
14h 59m2 stops
 Logo
1:00 pm - 10:37 pmEYW-MDW
10h 37m1 stop
Wed, Jun 25 - Sun, Jun 29

KAYAK's insights & trends for Midway to Florida Keys flights

Get data-powered insights and trends into flights from Midway to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest time of day to fly to Florida Keys?

The average price for all round-trip flights from Chicago Midway Airport to Florida Keys depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $159 on average. Morning departures are around 16% cheaper than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the evening, which is peak travel time and where the average cost of a ticket is $241.

What is the cheapest month to fly from Chicago Midway Airport to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Florida Keys, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Florida Keys is May, when tickets cost $163 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $351 and $326 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Florida Keys?

The average price of all round-trip flights from Chicago Midway Airport to Florida Keys clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago Midway Airport to Florida Keys, look for departures on Wednesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Florida Keys, Thursday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago Midway Airport to Florida Keys?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Florida Keys, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago Midway Airport to Florida Keys, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

November

High season

March

Cheapest flight

$63
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 2% 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 $79 one-way - $197 round-trip

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.
8.0
SouthwestOverall score based on 4274 reviews
8.6Crew
7.1Food
7.6Entertainment
8.2Boarding
8.0Comfort
Airline reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

10.0 ExcellentReginald, Mar 2025MDW - LGA
Read more Southwest reviews

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

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.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

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.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

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.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Terrible! They kept postponing and finally canceled our flight. They canceled so late. We had no other options but to drive to a different city and try to find a new flight to get onto our cruise. We still aren’t there yet and might not make it.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

The flight was on time. The seats are very narrow.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

No leg room AT all extremely uncomfortable flight water even cost 5 dollars

This was my first experience with Spirit. The flight was originally delayed because of mechanical problems. There was a major storm moving through our area later in the day. Spirit kept changing the gate and taking the plane for other flights. They did this 6 times until we left 7 hours later, right at the worse time. I am sure it is because they originally delayed the flight through their fault. They would have had to pay for everybody's hotel and later flight. It was a money decision. The pilot did an exceptional job flying and landing the plane in horrific weather. It was one of the roughest and shakiest landings that I have ever done in my extensive flying experience. I just can never go through this discount BS again. Spirit gave us a $30 voucher each for next travel and a $12 meal voucher... but that's nothing compared to sitting in an airport for 7 hours.

Seats were comfortable but dont recline at all. Checkin online was easy but didnt provide a gate until last minute. Flight attendants were very unkind, not friendly and didnt go over safety procedures in case of a crash. No free snacks or beverages, not even water.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

The booking was cancelled the next day. Spirit Airlines refunded Kayak cheapflay the full amount, but I was only refunded half. Costumer service is disgusting. Be careful. You can lose your money.

Kayak never booked my flight, I have received notifications the entire time the fights were to be used I went to the airport to find out despite receiving these emails to board my flight was never booked only to have to return home and miss the event I was scheduled for, inconvenient and devastating to say the least, customer service was very poor to only explain that my card had not been charged so that I shouldn’t worry. Yea great for you to say being that your not inconvenienced.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

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.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

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