MDW

$62 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 2/17. 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
$72
Overall average: $224
Frontier
Thu 2/19Sun 3/1
MIA - MDW • Non-stop
Cheapest one-way
$62
Typical prices: $109-$252
Frontier
Tue 2/17
MIA - MDW • 1 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, Feb 19 - Sun, Mar 1
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$72Frontier
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$73Frontier
Thu, Feb 12 - Sun, Feb 15
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$76Frontier
Thu, Feb 12 - Thu, Feb 19
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$79Frontier
Thu, Mar 5 - Sun, Mar 8
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$80Frontier
Thu, Feb 12 - Sun, Feb 15
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$81Frontier
Thu, Feb 12 - Sun, Feb 15
Multiple Airlines Logo
7:05 am - 11:27 am
MIA
-
MDW
5h 22m
1 stop
Multiple Airlines Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$99Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
7:30 am - 12:02 pm
EYW
-
MDW
5h 32m
1 stop
Delta Logo
6:00 am - 1:44 pm
MDW
-
EYW
6h 44m
1 stop
$484Delta
Wed, Feb 11 - Sun, Feb 15
Delta Logo
7:10 am - 11:59 am
EYW
-
MDW
5h 49m
1 stop
Delta Logo
11:01 am - 7:42 pm
MDW
-
EYW
7h 41m
1 stop
$584Delta
Mon, Feb 9 - Fri, Feb 13
Delta Logo
7:10 am - 11:59 am
EYW
-
MDW
5h 49m
1 stop
Delta Logo
12:45 pm - 7:42 pm
MDW
-
EYW
5h 57m
1 stop
$859Delta
Useful Info

Good to know

Low seasonDecember
Cheapest flight$62
Best time to beat the crowds but there is an average 11% increase 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.
8.0
SouthwestOverall score based on 4268 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

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.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

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.

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
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports