$53 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 9/29. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Florida

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Orlando
Orlandononstop$95
Miami
Miami1 stop$115
Fort Lauderdale
Fort Lauderdale1 stop$142
Tampa
Tampanonstop$106
Fort Myers
Fort Myers1 stop$143
West Palm Beach
West Palm Beach1 stop$210
Jacksonville
Jacksonville1 stop$178
Sarasota
Sarasota2 stops$262
Pensacola
Pensacola1 stop$249
Key West
Key West1 stop$269
Panama City
Panama City1 stop$287
Valparaiso
Valparaisononstop$238
Punta Gorda
Punta Gordanonstop$146
Tallahassee
Tallahassee1 stop$317
Gainesville
Gainesville1 stop$382
Orlando
Orlandononstop$95
Miami
Miami1 stop$115
Fort Lauderdale
Fort Lauderdale1 stop$142
Tampa
Tampanonstop$106
Fort Myers
Fort Myers1 stop$143
West Palm Beach
West Palm Beach1 stop$210
Jacksonville
Jacksonville1 stop$178
Sarasota
Sarasota2 stops$262
Pensacola
Pensacola1 stop$249
Key West
Key West1 stop$269
Panama City
Panama City1 stop$287
Valparaiso
Valparaisononstop$238
Punta Gorda
Punta Gordanonstop$146
Tallahassee
Tallahassee1 stop$317
Gainesville
Gainesville1 stop$382

Book Cheap Midway to Florida Plane Tickets

 
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

Fri, Oct 3 - Sun, Oct 5
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$95Frontier
Find Deal
Mon, Nov 3 - Sat, Nov 8
Frontier Logo
9:32 am - 1:14 pmMDW-MCO
2h 42mnonstop
Frontier Logo
8:30 am - 10:26 amMCO-MDW
2h 56mnonstop
$96Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Southwest Logo
1:40 pm - 5:35 pmMDW-FLL
2h 55mnonstop
Southwest Logo
6:30 am - 8:35 amFLL-MDW
3h 05mnonstop
$153Southwest
Find Deal
Mon, Sep 22 - Tue, Sep 23
Southwest Logo
8:00 am - 12:00 pmMDW-FLL
3h 00mnonstop
Southwest Logo
7:00 am - 9:10 amFLL-MDW
3h 10mnonstop
$171Southwest
Find Deal
Thu, Sep 25 - Thu, Sep 25
 Logo
6:20 am - 11:43 amMDW-JAX
4h 23m1 stop
 Logo
5:27 pm - 7:00 pmJAX-MDW
26h 33m1 stop
Fri, Sep 12 - Sun, Sep 14
 Logo
8:15 am - 3:21 pmMDW-JAX
6h 06m1 stop
 Logo
5:27 pm - 7:00 pmJAX-MDW
26h 33m1 stop
Tue, Sep 23 - Tue, Sep 23
Delta Logo
6:00 am - 11:40 amMDW-JAX
4h 40m1 stop
Delta Logo
5:01 pm - 9:36 pmJAX-MDW
5h 35m1 stop
$261Delta
Find Deal
Tue, Sep 30 - Tue, Oct 7
Delta Logo
12:43 pm - 7:17 pmMDW-PNS
6h 34m1 stop
Delta Logo
7:00 am - 11:53 amPNS-MDW
4h 53m1 stop
$264Delta
Find Deal
Fri, Nov 7 - Mon, Nov 10
Allegiant Air Logo
5:35 pm - 9:01 amMDW-EYW
14h 26m2 stops
Allegiant Air Logo
10:41 am - 3:22 pmEYW-MDW
5h 41m1 stop
$360Allegiant Air
Find Deal
Fri, Oct 24 - Mon, Oct 27
Allegiant Air Logo
2:45 pm - 8:55 pmMDW-EYW
5h 10m1 stop
Allegiant Air Logo
2:57 pm - 7:34 pmEYW-MDW
5h 37m1 stop
$456Allegiant Air
Find Deal
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Florida from Chicago Midway Airport found in the last 72 hours was to Tampa, at $44 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 $88.

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 $284, 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 $197 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $359 and $314 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 seasonJuly
Cheapest flight$53
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago Midway Airport to Orlando Airport

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 at night, when round-trip flights cost $278 on average. Morning departures are around 2% 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 $312.

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 $81 one-way - $156 round-trip; Tampa $98 one-way - $97 round-trip

Reviews of the 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 4238 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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!

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

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 great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

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!

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

I am very happy with my experience with Spirit Airlines. Both flights were on time. Boarding was very pleasant. Crew was very nice. Flights were amazing and we even arrived earlier than the schedule time. I am hoping Spirits keeps on having non stop flight from Ft Lauderdale to Hartford for many years to come.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

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.

Everything you need to know for your flight from Midway to Florida

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.