$49 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 11/17. 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

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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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Flight Deals

Cheap Flights from Midway to Florida

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Orlando
Orlando1 stop$100
Miami
Miaminonstop$101
Fort Lauderdale
Fort Lauderdalenonstop$105
Tampa
Tampanonstop$103
Fort Myers
Fort Myers1 stop$155
West Palm Beach
West Palm Beach1 stop$231
Jacksonville
Jacksonville1 stop$270
Sarasota
Sarasota2 stops$266
Pensacola
Pensacola1 stop$224
Key West
Key West1 stop$240
Panama City
Panama City1 stop$229
Valparaiso
Valparaisononstop$155
Punta Gorda
Punta Gordanonstop$120
Tallahassee
Tallahassee1 stop$317
Gainesville
Gainesville1 stop$362
Orlando
Orlando1 stop$100
Miami
Miaminonstop$101
Fort Lauderdale
Fort Lauderdalenonstop$105
Tampa
Tampanonstop$103
Fort Myers
Fort Myers1 stop$155
West Palm Beach
West Palm Beach1 stop$231
Jacksonville
Jacksonville1 stop$270
Sarasota
Sarasota2 stops$266
Pensacola
Pensacola1 stop$224
Key West
Key West1 stop$240
Panama City
Panama City1 stop$229
Valparaiso
Valparaisononstop$155
Punta Gorda
Punta Gordanonstop$120
Tallahassee
Tallahassee1 stop$317
Gainesville
Gainesville1 stop$362

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

Tue, Oct 28 - Thu, Oct 30
Multiple Airlines Logo
5:56 pm - 8:45 amMDW-MCO
13h 49m1 stop
Multiple Airlines Logo
7:15 am - 9:12 amMCO-MDW
2h 57mnonstop
$100Multiple Airlines
Find Deal
Sun, Dec 7 - Thu, Dec 11
Frontier Logo
6:30 am - 10:47 amMDW-MIA
3h 17mnonstop
Frontier Logo
11:42 am - 2:05 pmMIA-MDW
3h 23mnonstop
$101Frontier
Find Deal
Tue, Oct 28 - Fri, Oct 31
Multiple Airlines Logo
5:56 pm - 8:45 amMDW-MCO
13h 49m1 stop
Multiple Airlines Logo
6:35 am - 8:32 amMCO-MDW
2h 57mnonstop
$101Multiple Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
2:05 pm - 6:05 pmMDW-MIA
3h 00mnonstop
Frontier Logo
7:05 pm - 9:22 pmMIA-MDW
3h 17mnonstop
$102Frontier
Find Deal
Sun, Nov 16 - Tue, Nov 18
Southwest Logo
5:45 am - 9:45 amMDW-FLL
3h 00mnonstop
Southwest Logo
6:50 am - 8:55 amFLL-MDW
3h 05mnonstop
$105Southwest
Find Deal
Mon, Nov 10 - Fri, Nov 14
Southwest Logo
7:15 pm - 11:15 pmMDW-FLL
3h 00mnonstop
Southwest Logo
9:15 pm - 11:25 pmFLL-MDW
3h 10mnonstop
$115Southwest
Find Deal
Wed, Dec 3 - Sun, Dec 7
Delta Logo
5:38 pm - 12:35 amMDW-RSW
5h 57m1 stop
Delta Logo
5:35 am - 9:54 amRSW-MDW
5h 19m1 stop
$217Delta
Find Deal
Wed, Nov 5 - Tue, Nov 11
Delta Logo
10:40 am - 3:05 pmMDW-PNS
4h 25m1 stop
Delta Logo
6:00 am - 9:52 amPNS-MDW
3h 52m1 stop
$229Delta
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
$298Allegiant Air
Find Deal
Mon, Nov 24 - Wed, Nov 26
Allegiant Air Logo
7:36 pm - 9:35 amMDW-EYW
12h 59m1 stop
Allegiant Air Logo
10:01 am - 6:54 pmEYW-MDW
9h 53m1 stop
$306Allegiant 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 Orlando, at $95 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 $95.

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 $332, 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 August, when tickets cost $202 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $366 and $333 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 Friday 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 seasonSeptember
Cheapest flight$49
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 12% 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 in the afternoon, when round-trip flights cost $270 on average. Morning departures are around 1% 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 $307.

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 $82 one-way - $180 round-trip; Miami $78 one-way - $210 round-trip; Tampa $85 one-way - $147 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 4240 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
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!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

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

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

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.

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

Very easy boarding! Crew was fantastic and offered us refreshments quickly and efficiently. Quick, nice flight!

My baggage broke and they did not offer me anything. No conversation

It was not good at all, I think the crew could be kinder

Cheap flight but really uncomfortable. Seat cushions flimsy. Jammed in middle seat when flight is not full. They don’t even give you water

My initial flight got overbooked whilst waiting at the gate, and they rebooked me on a later INDIRECT flight!. No offer of a refund

Don't board the plane and have us sit for 2 hours and go nowhere!

I never made my flight because of their poor service, as I said in my other review: I never made this flight. When I got to the airport I had a message to say that the flight was delayed and would be getting into Fort Lauderdale at 10 pm. My connecting flight was due to leave around 10:10 pm so there is no way I would have made the connection. I went back to the Spirit desk and tried to explain this to a desk agent who didn't understand. Eventually her supervisor came over and explained it. The desk agent was unhelpful and only offered options that would have required getting a hotel overnight. She offered no hotel or meal vouchers and when I said that it seemed my only option was to go to another airline she told me I needed to make a decision because they were closing the desk and would not be back till 3 pm. I went to Delta and had to pay extra but they could help get me back to Orlando. I now have to file a claim against Spirit and I am just glad I paid for insurance. Very unhappy and very poor service.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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.

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