MDW

$101 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 7/8. 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

Tue, Jul 21 - Tue, Jul 28
Southwest Logo
4:00 pm - 6:10 pm
MIA
-
MDW
3h 10mnonstop
Southwest Logo
11:45 am - 3:45 pm
MDW
-
MIA
3h 00mnonstop
$171Southwest
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
4:00 pm - 6:10 pm
MIA
-
MDW
3h 10mnonstop
Southwest Logo
8:10 am - 2:25 pm
MDW
-
MIA
5h 15m
1 stop
$177Southwest
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
4:00 pm - 6:10 pm
MIA
-
MDW
3h 10mnonstop
Southwest Logo
5:35 am - 3:10 pm
MDW
-
MIA
8h 35m
1 stop
$181Southwest
Tue, Jul 14 - Tue, Jul 21
Southwest Logo
11:45 am - 3:55 pm
MIA
-
MDW
5h 10m
1 stop
Southwest Logo
8:10 am - 2:25 pm
MDW
-
MIA
5h 15m
1 stop
$182Southwest
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
11:45 am - 3:55 pm
MIA
-
MDW
5h 10m
1 stop
Southwest Logo
5:35 am - 3:10 pm
MDW
-
MIA
8h 35m
1 stop
$186Southwest
Thu, Jul 30 - Thu, Aug 6
Allegiant Air Logo
10:55 am - 2:38 pm
EYW
-
MDW
28h 43m
1 stop
Allegiant Air Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
$281Allegiant Air
Tue, Jul 14 - Thu, Jul 16
Multiple Airlines Logo
1:14 pm - 10:03 pm
EYW
-
MDW
9h 49m
2 stops
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
$286Multiple Airlines
Tue, Jul 14 - Thu, Jul 16
Multiple Airlines Logo
1:14 pm - 10:03 pm
EYW
-
MDW
9h 49m
2 stops
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
$293Multiple Airlines
Tue, Jul 14 - Thu, Jul 16
Delta Logo
11:56 am - 4:15 pm
EYW
-
MDW
5h 19m
1 stop
Delta Logo
12:41 pm - 7:51 pm
MDW
-
EYW
6h 10m
1 stop
$587Delta
Mon, Jul 6 - Tue, Jul 14
Delta Logo
6:24 pm - 10:17 pm
EYW
-
MDW
4h 53m
1 stop
Delta Logo
11:05 am - 7:51 pm
MDW
-
EYW
7h 46m
1 stop
$619Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 1% 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.
7.9
SouthwestOverall score based on 4235 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
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.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

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.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

It was an early flight and most people napped/slept and the crew let us which was nice.

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.

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
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

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