MDW

$66 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 3/19. 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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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, Mar 31 - Fri, Apr 10
Multiple Airlines Logo
3:12 pm - 8:54 pm
MIA
-
MDW
6h 42m
1 stop
Multiple Airlines Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
$130Multiple Airlines
Fri, Mar 27 - Mon, Mar 30
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$139Frontier
Thu, Apr 9 - Sat, Apr 11
Frontier Logo
9:10 am - 8:07 pm
MIA
-
MDW
11h 57m
1 stop
Frontier Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
$140Frontier
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
3:12 pm - 10:14 pm
MIA
-
MDW
8h 02m
1 stop
Multiple Airlines Logo
2:15 pm - 12:49 am
MDW
-
MIA
9h 34m
1 stop
$141Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
5:49 pm - 1:00 pm
MIA
-
MDW
20h 11m
1 stop
Multiple Airlines Logo
2:15 pm - 12:49 am
MDW
-
MIA
9h 34m
1 stop
$142Multiple Airlines
Wed, Apr 15 - Sat, Apr 18
Frontier Logo
1:10 pm - 7:31 pm
MIA
-
MDW
7h 21m
1 stop
Frontier Logo
7:34 pm - 10:12 am
MDW
-
MIA
13h 38m
1 stop
$145Frontier
Tue, Apr 21 - Sat, Apr 25
Frontier Logo
1:05 pm - 7:31 pm
MIA
-
MDW
7h 26m
1 stop
Frontier Logo
7:34 pm - 10:12 am
MDW
-
MIA
13h 38m
1 stop
$148Frontier
Thu, Aug 6 - Wed, Aug 12
Delta Logo
6:00 pm - 9:45 pm
EYW
-
MDW
4h 45m
1 stop
Delta Logo
6:00 am - 1:09 pm
MDW
-
EYW
6h 09m
1 stop
$329Delta
Thu, Mar 26 - Mon, Mar 30
Delta Logo
11:43 am - 5:22 pm
EYW
-
MDW
6h 39m
1 stop
Delta Logo
12:47 pm - 7:41 pm
MDW
-
EYW
5h 54m
1 stop
$444Delta
Thu, Apr 9 - Mon, Apr 13
Delta Logo
6:25 pm - 10:31 pm
EYW
-
MDW
5h 06m
1 stop
Delta Logo
6:00 am - 1:44 pm
MDW
-
EYW
6h 44m
1 stop
$464Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$51
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 2% 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 4318 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

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.

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
Saint John
Griffith

Everything you need to know for your flight to Midway

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