MDW

$90 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 7/2. 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.
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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Florida Keys to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Florida Keys to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
6:30 am - 8:40 amMIA-MDW
3h 10mnonstop
Southwest Logo
7:10 pm - 11:10 pmMDW-MIA
3h 00mnonstop
$179Southwest
Find Deal
Wed, Jul 2 - Sat, Jul 5
Southwest Logo
7:00 am - 9:10 amMIA-MDW
3h 10mnonstop
Southwest Logo
5:10 pm - 9:05 pmMDW-MIA
2h 55mnonstop
$197Southwest
Find Deal
Fri, May 30 - Tue, Jun 3
Southwest Logo
6:45 am - 8:55 amMIA-MDW
3h 10mnonstop
Southwest Logo
6:00 am - 3:40 pmMDW-MIA
8h 40m2 stops
$203Southwest
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Fri, Jun 27 - Tue, Jul 1
Frontier Logo
7:24 pm - 7:43 pmMIA-MDW
25h 19m1 stop
Frontier Logo
7:05 am - 8:05 amMDW-MIA
24h 00m1 stop
$205Frontier
Find Deal
Thu, May 29 - Mon, Jun 2
Frontier Logo
3:55 pm - 11:39 pmMIA-MDW
8h 44m1 stop
Frontier Logo
6:15 am - 11:31 pmMDW-MIA
16h 16m1 stop
$211Frontier
Find Deal
Thu, May 15 - Mon, May 19
Frontier Logo
7:24 pm - 7:43 pmMIA-MDW
25h 19m1 stop
Frontier Logo
3:25 pm - 8:35 pmMDW-MIA
28h 10m1 stop
$214Frontier
Find Deal
Thu, May 29 - Thu, Jun 5
Frontier Logo
7:24 pm - 7:43 pmMIA-MDW
25h 19m1 stop
Frontier Logo
4:54 pm - 8:05 amMDW-MIA
14h 11m1 stop
$216Frontier
Find Deal
Thu, May 29 - Tue, Jun 3
Delta Logo
5:30 am - 9:41 amMIA-MDW
5h 11m1 stop
Delta Logo
12:44 pm - 9:16 pmMDW-MIA
7h 32m1 stop
$217Delta
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Sat, Jun 14 - Tue, Jun 17
Delta Logo
7:00 am - 11:53 amMIA-MDW
5h 53m1 stop
Delta Logo
4:15 pm - 12:37 amMDW-MIA
7h 22m1 stop
$218Delta
Find Deal
Wed, May 21 - Sat, May 24
Delta Logo
6:00 am - 11:55 amMIA-MDW
6h 55m1 stop
Delta Logo
6:00 am - 12:59 pmMDW-MIA
5h 59m1 stop
$228Delta
Find Deal
Tue, Aug 12 - Tue, Aug 26
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Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$90
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 4% 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.

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 4294 reviews
7.1Food
8.2Boarding
8.6Crew
7.6Entertainment
8.0Comfort
Airline reviews

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.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

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.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

They switched my flight to Spirit, Never using Kayak again,

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.

Asked for a seat change to be w my wife at the gate they were great in sorting it out to make it happen

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

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.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

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