$96 Find Cheap Flights from Chicago Midway Airport to Florida Keys - Compare and Save

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 9/30. 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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Cheap Flights from Midway to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miaminonstop$177
Key West
Key West1 stop$323
Miami
Miaminonstop$177
Key West
Key West1 stop$323

Book Cheap Midway to Florida Keys Plane Tickets

 
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

Wed, Aug 26 - Sat, Aug 29
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
Southwest Logo
6:30 am - 10:40 am
MIA
-
MDW
5h 10m
1 stop
$177Southwest
Mon, Sep 21 - Thu, Sep 24
Southwest Logo
7:25 am - 3:20 pm
MDW
-
MIA
6h 55m
1 stop
Southwest Logo
7:15 am - 9:20 am
MIA
-
MDW
3h 05mnonstop
$181Southwest
Tue, Aug 18 - Thu, Aug 20
Frontier Logo
6:05 am - 1:32 pm
MDW
-
MIA
6h 27m
1 stop
Frontier Logo
5:28 pm - 10:47 pm
MIA
-
MDW
6h 19m
1 stop
$181Frontier
Thu, Oct 1 - Wed, Oct 7
Southwest Logo
3:45 pm - 11:05 pm
MDW
-
MIA
6h 20m
1 stop
Southwest Logo
12:35 pm - 2:40 pm
MIA
-
MDW
3h 05mnonstop
$181Southwest
Thu, Nov 12 - Mon, Nov 16
Frontier Logo
7:25 am - 6:12 pm
MDW
-
MIA
9h 47m
1 stop
Frontier Logo
6:45 am - 10:58 am
MIA
-
MDW
5h 13m
1 stop
$182Frontier
Thu, Nov 12 - Mon, Nov 16
Frontier Logo
7:25 am - 6:12 pm
MDW
-
MIA
9h 47m
1 stop
Frontier Logo
6:45 am - 10:58 am
MIA
-
MDW
5h 13m
1 stop
$182Frontier
Wed, Sep 2 - Sun, Sep 6
Delta Logo
10:54 am - 4:57 pm
MDW
-
MIA
5h 03m
1 stop
Delta Logo
6:00 am - 10:10 am
MIA
-
MDW
5h 10m
1 stop
$217Delta
Wed, Nov 18 - Tue, Dec 1
Delta Logo
6:00 am - 11:46 am
MDW
-
MIA
4h 46m
1 stop
Delta Logo
8:00 am - 12:05 pm
MIA
-
MDW
5h 05m
1 stop
$217Delta
Thu, Aug 13 - Sun, Aug 16
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
12:05 pm - 2:59 pm
EYW
-
MDW
27h 54m
2 stops
$349Multiple Airlines
Sun, Oct 11 - Fri, Oct 16
Multiple Airlines Logo
12:03 pm - 2:04 pm
MDW
-
EYW
25h 01m
2 stops
Multiple Airlines Logo
10:14 am - 3:40 pm
EYW
-
MDW
6h 26m
1 stop
$352Multiple Airlines
Booking Insights

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 in the afternoon, when round-trip flights cost $146 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally at night, which is peak travel time and where the average cost of a ticket is $390.

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 $411, 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 October, when tickets cost $173 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $395 and $395 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 Thursdays 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low season

September

Cheapest flight

$96
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 13% 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.

Reviews of the top 4 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 4229 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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

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 experience. WiFi worked on this leg of My trip

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

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

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

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.

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

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

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.

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.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports