MDW

$43 Find Cheap Flights from Florida Keys to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 10/16. 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

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Cheap Flights from Florida Keys to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Florida Keys to Midway 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 Florida Keys to Midway

Fri, Sep 19 - Sun, Sep 21
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
Southwest Logo
2:45 pm - 6:45 pmMDW-MIA
3h 00mnonstop
$137Southwest
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Fri, Sep 26 - Sun, Sep 28
Southwest Logo
6:15 pm - 12:05 amMIA-MDW
6h 50m1 stop
Southwest Logo
2:45 pm - 6:45 pmMDW-MIA
3h 00mnonstop
$147Southwest
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Tue, Sep 23 - Mon, Sep 29
Southwest Logo
7:10 am - 1:25 pmMIA-MDW
7h 15m2 stops
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
$152Southwest
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Mon, Oct 27 - Thu, Oct 30
Frontier Logo
6:53 pm - 9:08 pmMIA-MDW
3h 15mnonstop
Frontier Logo
4:29 pm - 6:19 amMDW-MIA
12h 50m1 stop
$204Frontier
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Sat, Sep 6 - Mon, Sep 8
Delta Logo
8:10 am - 12:28 pmMIA-MDW
5h 18m1 stop
Delta Logo
1:08 pm - 9:30 pmMDW-MIA
7h 22m1 stop
$215Delta
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Sat, Sep 13 - Sat, Sep 20
Delta Logo
8:10 am - 12:28 pmMIA-MDW
5h 18m1 stop
Delta Logo
4:25 pm - 12:23 amMDW-MIA
6h 58m1 stop
$217Delta
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Thu, Oct 9 - Thu, Oct 23
Frontier Logo
6:53 pm - 9:08 pmMIA-MDW
3h 15mnonstop
Frontier Logo
10:03 pm - 2:03 amMDW-MIA
3h 00mnonstop
$228Frontier
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Wed, Aug 13 - Wed, Aug 20
Delta Logo
4:25 pm - 9:44 pmMIA-MDW
6h 19m1 stop
Delta Logo
6:42 pm - 12:24 amMDW-MIA
4h 42m1 stop
$237Delta
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Sun, Oct 5 - Thu, Oct 23
Frontier Logo
9:16 pm - 7:11 amMIA-MDW
10h 55m1 stop
Frontier Logo
10:03 pm - 2:03 amMDW-MIA
3h 00mnonstop
$248Frontier
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Fri, Oct 17 - Mon, Oct 20
Frontier Logo
6:42 pm - 11:25 pmMIA-MDW
5h 43m1 stop
Frontier Logo
10:03 pm - 2:03 amMDW-MIA
3h 00mnonstop
$251Frontier
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Good to know

Low seasonJanuary
Cheapest flight$43
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Miami to Chicago Midway Airport

FAQs for booking Florida Keys to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Florida Keys to Chicago Midway Airport?

    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 Florida Keys to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Florida Keys to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from 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 Florida Keys to Chicago Midway Airport?

    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 to Chicago Midway Airport with an airline and back to Florida Keys with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida Keys to Chicago Midway Airport?

    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 to Chicago Midway Airport from 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 airlines flying from Florida Keys to Midway

 
Need help choosing which airline to fly with from Florida Keys to Midway? 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 4241 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

They switched my flight to Spirit, Never using Kayak again,

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