$71 Find Cheap Flights from Chicago Midway Airport to Florida

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Florida departing on 10/2. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Florida

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida.
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Best Florida Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Orlando
Orlandononstop$126
Miami
Miami1 stop$145
Fort Lauderdale
Fort Lauderdale1 stop$145
Tampa
Tampanonstop$128
Fort Myers
Fort Myersnonstop$157
West Palm Beach
West Palm Beach1 stop$234
Jacksonville
Jacksonvillenonstop$157
Sarasota
Sarasota2 stops$254
Pensacola
Pensacola1 stop$177
Key West
Key West1 stop$269
Panama City
Panama City1 stop$167
Valparaiso
Valparaisononstop$87
Punta Gorda
Punta Gordanonstop$115
Tallahassee
Tallahassee1 stop$357
Gainesville
Gainesville1 stop$329
Orlando
Orlandononstop$126
Miami
Miami1 stop$145
Fort Lauderdale
Fort Lauderdale1 stop$145
Tampa
Tampanonstop$128
Fort Myers
Fort Myersnonstop$157
West Palm Beach
West Palm Beach1 stop$234
Jacksonville
Jacksonvillenonstop$157
Sarasota
Sarasota2 stops$254
Pensacola
Pensacola1 stop$177
Key West
Key West1 stop$269
Panama City
Panama City1 stop$167
Valparaiso
Valparaisononstop$87
Punta Gorda
Punta Gordanonstop$115
Tallahassee
Tallahassee1 stop$357
Gainesville
Gainesville1 stop$329

Cheap Flights from Midway to Florida

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Florida 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 Midway to Florida

Sat, Sep 13 - Sun, Sep 21
Frontier Logo
12:51 pm - 4:29 pmMDW-MCO
2h 38mnonstop
Frontier Logo
5:45 am - 7:39 amMCO-MDW
2h 54mnonstop
$126Frontier
Find Deal
Mon, Sep 15 - Sun, Sep 21
Frontier Logo
8:34 am - 12:15 pmMDW-MCO
2h 41mnonstop
Frontier Logo
5:45 am - 7:39 amMCO-MDW
2h 54mnonstop
$127Frontier
Find Deal
Tue, Sep 16 - Sat, Sep 20
Southwest Logo
6:00 pm - 10:00 pmMDW-FLL
3h 00mnonstop
Southwest Logo
6:45 am - 8:45 amFLL-MDW
3h 00mnonstop
$157Southwest
Find Deal
Wed, Oct 8 - Wed, Oct 15
Southwest Logo
7:50 am - 11:30 amMDW-RSW
2h 40mnonstop
Southwest Logo
4:20 pm - 6:10 pmRSW-MDW
2h 50mnonstop
$157Southwest
Find Deal
Sat, Jul 26 - Tue, Jul 29
Delta Logo
4:22 pm - 12:14 amMDW-TPA
6h 52m1 stop
Delta Logo
7:50 am - 11:58 amTPA-MDW
5h 08m1 stop
$197Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
Delta Logo
5:25 pm - 10:43 pmMDW-ECP
5h 18m1 stop
Delta Logo
11:15 am - 4:23 pmECP-MDW
5h 08m1 stop
$197Delta
Find Deal
Fri, Jul 18 - Mon, Jul 21
Allegiant Air Logo
10:31 am - 9:55 amMDW-FLL
22h 24m1 stop
Allegiant Air Logo
6:00 am - 2:04 pmFLL-MDW
9h 04m1 stop
$199Allegiant Air
Find Deal
Fri, Aug 1 - Sun, Aug 10
Allegiant Air Logo
1:11 pm - 9:55 amMDW-FLL
19h 44m1 stop
Allegiant Air Logo
8:05 pm - 12:21 pmFLL-MDW
17h 16m1 stop
$202Allegiant Air
Find Deal
Fri, Aug 1 - Sun, Aug 10
 Logo
1:11 pm - 9:26 pmMDW-FLL
31h 15m2 stops
 Logo
8:05 pm - 12:21 pmFLL-MDW
17h 16m1 stop
Fri, Jul 11 - Sun, Jul 13
 Logo
10:31 am - 8:00 amMDW-FLL
20h 29m2 stops
 Logo
8:05 pm - 9:41 amFLL-MDW
14h 36m1 stop
Useful Info

KAYAK's insights & trends for Midway to Florida flights

Get data-powered insights and trends into flights from Midway to Florida to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Florida flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Florida.

The cheapest ticket to Florida from Chicago Midway Airport found in the last 72 hours was to Tampa, at $111 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Orlando Airport (MCO), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $111.

Can I save money by flying with a layover from Chicago Midway Airport to Florida?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $307, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Florida?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Florida, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Florida is September, when tickets cost $173 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $364 and $337 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Florida?

The average price of all round-trip flights from Chicago Midway Airport to Florida clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Florida on a Thursday and more expensive on a Wednesday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Tuesdays for better deals.

How far in advance should I book a flight from Chicago Midway Airport to Florida?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Florida, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Florida, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.


Good to know

Low seasonAugust
High seasonMarch
Cheapest flight$71
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago Midway Airport to Tampa

FAQs - booking Florida flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Florida?

    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 Chicago Midway Airport to Florida.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Florida?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Florida 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 Chicago Midway Airport to Florida?

    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 from Chicago Midway Airport to Florida with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Florida?

    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 from Chicago Midway Airport to Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Florida?

    The cheapest time of day to fly to Florida is generally in the afternoon, when round-trip flights cost $268 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Florida is generally in the morning, which is peak travel time and where the average cost of a ticket is $316.

Top tips for finding cheap flights to Florida

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Orlando $88 one-way - $232 round-trip; Tampa $94 one-way - $185 round-trip

Top 5 airlines serving from Midway to Florida

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Florida. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Florida? 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 4287 reviews
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

6.0 GoodVincent, May 2025MDW - MCO
Read more Southwest reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

My experience with spirit was terrible. Customer service was terrible. Flight got canceled abruptly with no accommodations made for the inconvenience or any sort of help. I was unable to rebook a new flight.

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

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