MDW

$64 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 1/17. 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
$86
Overall average: $133
Frontier
Thu 1/8Thu 1/15
MIA - MDW • 1 stop
Cheapest non-stop
$101
Typical prices: $69-$343
Frontier
Wed 12/24Wed 12/31
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

Thu, Jan 8 - Thu, Jan 15
Frontier Logo
5:20 am - 11:31 am
MIA
-
MDW
7h 11m1 stop
Frontier Logo
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$86Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
4:29 pm - 6:54 pm
MIA
-
MDW
3h 25mnonstop
Frontier Logo
6:10 am - 2:15 pm
MDW
-
MIA
7h 05m1 stop
$89Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
4:29 pm - 6:54 pm
MIA
-
MDW
3h 25mnonstop
Frontier Logo
6:10 am - 2:15 pm
MDW
-
MIA
7h 05m1 stop
$90Frontier
Wed, Feb 25 - Sun, Mar 1
Frontier Logo
12:10 pm - 7:07 pm
MIA
-
MDW
7h 57m1 stop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$94Frontier
Tue, Feb 24 - Thu, Feb 26
Frontier Logo
12:20 pm - 7:07 pm
MIA
-
MDW
7h 47m1 stop
Frontier Logo
5:16 pm - 12:42 am
MDW
-
MIA
6h 26m1 stop
$98Frontier
Thu, Jan 8 - Thu, Jan 15
Frontier Logo
5:20 am - 11:31 am
MIA
-
MDW
7h 11m1 stop
Frontier Logo
11:05 am - 1:18 am
MDW
-
MIA
13h 13m1 stop
$99Frontier
Wed, Jan 14 - Fri, Jan 16
Frontier Logo
5:15 am - 10:31 am
MIA
-
MDW
6h 16m1 stop
Frontier Logo
8:04 pm - 12:13 am
MDW
-
MIA
3h 09mnonstop
$103Frontier
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
4:44 pm - 7:09 pm
MIA
-
MDW
3h 25mnonstop
Frontier Logo
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$106Frontier
Wed, Jan 21 - Thu, Jan 29
Delta Logo
6:06 pm - 10:22 pm
EYW
-
MDW
5h 16m1 stop
Delta Logo
10:48 am - 5:11 pm
MDW
-
EYW
5h 23m1 stop
$269Delta
Mon, Dec 29 - Mon, Jan 12
Delta Logo
6:20 pm - 10:22 pm
EYW
-
MDW
5h 02m1 stop
Delta Logo
11:21 am - 5:11 pm
MDW
-
EYW
4h 50m1 stop
$299Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% 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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

2.0 MediocreCharity, Nov 2025
MSP - MDW
Read more Southwest reviews

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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 got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

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.

Traveling to a place near Midway?

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

Everything you need to know for your flight to Midway

Information on your arrival and departure airports