MDW

$94 Find Cheap Flights from Florida Keys to Chicago Midway Airport - 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 to Midway departing on 9/10. 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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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, Aug 27 - Tue, Sep 1
Frontier Logo
5:28 pm - 10:47 pm
MIA
-
MDW
6h 19m
1 stop
Frontier Logo
6:05 am - 1:32 pm
MDW
-
MIA
6h 27m
1 stop
$180Frontier
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
7:15 am - 9:20 am
MIA
-
MDW
3h 05mnonstop
Southwest Logo
5:30 am - 3:20 pm
MDW
-
MIA
8h 50m
1 stop
$181Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
7:15 am - 9:20 am
MIA
-
MDW
3h 05mnonstop
Southwest Logo
5:30 am - 3:20 pm
MDW
-
MIA
8h 50m
1 stop
$181Southwest
Thu, Sep 3 - Sat, Sep 12
Southwest Logo
7:15 am - 9:20 am
MIA
-
MDW
3h 05mnonstop
Southwest Logo
6:45 am - 1:35 pm
MDW
-
MIA
5h 50m
1 stop
$181Southwest
Thu, Nov 5 - Tue, Nov 10
Frontier Logo
6:45 am - 10:58 am
MIA
-
MDW
5h 13m
1 stop
Frontier Logo
12:03 pm - 6:12 pm
MDW
-
MIA
5h 09m
1 stop
$186Frontier
Tue, Sep 8 - Sat, Sep 12
Frontier Logo
5:28 pm - 10:47 pm
MIA
-
MDW
6h 19m
1 stop
Frontier Logo
1:06 pm - 10:00 pm
MDW
-
MIA
7h 54m
1 stop
$193Frontier
Thu, Oct 8 - Wed, Oct 14
Frontier Logo
6:00 am - 12:07 pm
MIA
-
MDW
7h 07m
1 stop
Frontier Logo
6:40 am - 6:22 pm
MDW
-
MIA
10h 42m
1 stop
$197Frontier
Mon, Aug 17 - Wed, Aug 19
Delta Logo
3:59 pm - 10:36 pm
MIA
-
MDW
7h 37m
1 stop
Delta Logo
9:24 am - 5:37 pm
MDW
-
MIA
7h 13m
1 stop
$217Delta
Thu, Jan 7 - Sat, Jan 9
Delta Logo
6:00 am - 9:52 am
MIA
-
MDW
4h 52m
1 stop
Delta Logo
1:05 pm - 8:54 pm
MDW
-
MIA
6h 49m
1 stop
$217Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
1:12 pm - 6:33 pm
MIA
-
MDW
6h 21m
1 stop
Delta Logo
5:10 pm - 12:55 am
MDW
-
MIA
6h 45m
1 stop
$217Delta
Useful Info

Good to know

Low season

January

Cheapest flight

$94
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 8% 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 4230 reviews
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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.

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 flight was great. We were not offered any beverages though. And there was no real turbulence, so not sure why.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Flight was fine but new boarding policy was a drag Xtra time passenger group And Waiting until entire bridge empties before calling a list preferred... Waste of time

Wish that they would space out the boarding a little. COVID is still around and is real. No entertainment. Miss the peanuts.

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.

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

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

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

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

The trip was unremarkable which is good. Crew was very professional and courteous.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

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
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports