$69 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 9/4. 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
1 adult, Economy

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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Flights Deals

Best Florida Keys Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miaminonstop$137
Key West
Key West1 stop$289
Miami
Miaminonstop$137
Key West
Key West1 stop$289

Cheap Flights from Midway to Florida Keys

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Florida Keys

Thu, Aug 21 - Mon, Aug 25
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
$137Southwest
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Thu, Aug 21 - Mon, Aug 25
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
6:15 pm - 12:05 amMIA-MDW
6h 50m1 stop
$147Southwest
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Thu, Aug 21 - Tue, Aug 26
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
11:40 am - 7:10 pmMIA-MDW
8h 30m2 stops
$152Southwest
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Thu, Sep 11 - Mon, Sep 15
Southwest Logo
3:20 pm - 10:10 pmMDW-MIA
5h 50m1 stop
Southwest Logo
5:05 pm - 10:00 pmMIA-MDW
5h 55m1 stop
$157Southwest
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Sun, Oct 19 - Sun, Oct 26
Frontier Logo
10:03 pm - 2:03 amMDW-MIA
3h 00mnonstop
Frontier Logo
6:53 pm - 9:08 pmMIA-MDW
3h 15mnonstop
$193Frontier
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Thu, Oct 9 - Mon, Oct 13
Frontier Logo
10:03 pm - 2:03 amMDW-MIA
3h 00mnonstop
Frontier Logo
6:53 pm - 9:08 pmMIA-MDW
3h 15mnonstop
$206Frontier
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Tue, Jul 29 - Tue, Aug 5
Delta Logo
12:43 pm - 7:33 pmMDW-MIA
5h 50m1 stop
Delta Logo
3:55 pm - 9:42 pmMIA-MDW
6h 47m1 stop
$217Delta
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Wed, Jul 30 - Wed, Aug 6
Delta Logo
9:25 am - 5:10 pmMDW-MIA
6h 45m1 stop
Delta Logo
12:46 pm - 6:40 pmMIA-MDW
6h 54m1 stop
$222Delta
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Thu, Jul 31 - Thu, Aug 7
Allegiant Air Logo
11:37 am - 4:36 pmMDW-EYW
27h 59m2 stops
Allegiant Air Logo
4:20 pm - 12:21 pmEYW-MDW
21h 01m1 stop
$303Allegiant Air
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Thu, Jul 31 - Thu, Aug 7
Allegiant Air Logo
11:37 am - 4:36 pmMDW-EYW
27h 59m2 stops
Allegiant Air Logo
8:54 am - 12:21 pmEYW-MDW
28h 27m2 stops
$353Allegiant Air
Find Deal
Useful Info

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.

Can I save money by flying with a layover from Chicago Midway Airport to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $341, prices are generally cheapest when you fly direct.

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 February, when tickets cost $175 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is $341 and $341 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 4 weeks before departure.


Good to know

Low seasonMay
High seasonDecember
Cheapest flight$69
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 26% 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 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.

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

    The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $183 on average. Morning departures are around 21% 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 $283.

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 4278 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

6.0 GoodVincent, May 2025MDW - MCO
Read more Southwest reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

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 was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

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.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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,

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

My experience with spirit was terrible. Customer service was terrible. Flight got canceled abruptly with no accommodations made for the inconvenience or any sort of help. I was unable to rebook a new flight.

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

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

Everything you need to know for your flight to Florida Keys

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