MDW

$67 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 11/18. 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, 0 bags

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Everything you should know

Cheapest round-trip
$96
Overall average: $236
Frontier
Sat 11/15Mon 11/17
MIA - MDW • Non-stop
Cheapest non-stop
$108
Typical prices: $138-$198
Frontier
Thu 12/11Sat 12/13
MIA - MDW • Non-stop
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Flight Deals
Useful Info
Flight Deals

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

Sat, Nov 15 - Mon, Nov 17
Frontier Logo
7:05 pm - 9:22 pmMIA-MDW
3h 17mnonstop
Frontier Logo
1:37 pm - 12:34 amMDW-MIA
9h 57m1 stop
$96Frontier
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Wed, Dec 31 - Tue, Jan 6
Multiple Airlines Logo
12:10 pm - 2:37 pmMIA-MDW
3h 27mnonstop
Multiple Airlines Logo
6:00 am - 9:04 pmMDW-MIA
14h 04m1 stop
$98Multiple Airlines
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Wed, Dec 24 - Wed, Jan 7
Frontier Logo
5:30 am - 10:12 pmMIA-MDW
17h 42m1 stop
Frontier Logo
3:52 pm - 8:02 pmMDW-MIA
3h 10mnonstop
$100Frontier
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Tue, Dec 2 - Sat, Dec 6
Frontier Logo
5:58 pm - 8:46 amMIA-MDW
15h 48m1 stop
Frontier Logo
2:59 pm - 7:09 pmMDW-MIA
3h 10mnonstop
$104Frontier
Find Deal
Sat, Nov 15 - Mon, Nov 17
Frontier Logo
7:05 pm - 9:22 pmMIA-MDW
3h 17mnonstop
Frontier Logo
9:15 am - 7:15 pmMDW-MIA
9h 00m1 stop
$106Frontier
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Thu, Dec 11 - Sat, Dec 13
Frontier Logo
7:26 pm - 9:53 pmMIA-MDW
3h 27mnonstop
Frontier Logo
2:59 pm - 7:09 pmMDW-MIA
3h 10mnonstop
$108Frontier
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Wed, Dec 24 - Wed, Jan 7
Multiple Airlines Logo
9:05 pm - 5:38 pmMIA-MDW
21h 33m1 stop
Multiple Airlines Logo
6:00 am - 1:06 pmMDW-MIA
6h 06m1 stop
$130Multiple Airlines
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Wed, Jan 7 - Sun, Jan 11
Southwest Logo
2:35 pm - 4:50 pmMIA-MDW
3h 15mnonstop
Southwest Logo
9:40 am - 1:45 pmMDW-MIA
3h 05mnonstop
$157Southwest
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Tue, Feb 24 - Tue, Mar 10
Delta Logo
7:00 am - 12:01 pmEYW-MDW
6h 01m1 stop
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
$269Delta
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Thu, Feb 12 - Tue, Feb 17
Delta Logo
7:00 am - 12:01 pmEYW-MDW
6h 01m1 stop
Delta Logo
10:35 am - 5:13 pmMDW-EYW
5h 38m1 stop
$294Delta
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$67
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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 4242 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

10.0 ExcellentMelissa, Sep 2025MSY - MDW
Read more Southwest reviews

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

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.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
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Saint Joseph
Hammond
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Chesterton
Schererville
Munster
Porter
Monticello
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Griffith

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