$44 Find Cheap Flights from Illinois to Florida

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Low seasonSeptember
Cheapest flight$44
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago Midway Airport to Orlando

Flights from Illinois to Florida: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Illinois to Florida 
Verified travelerFlew with American AirlinesORD-TPADec 2024
I recommend having movies and songs downloaded on your device.
AyannaFlew with Spirit AirlinesORD-TPAMay 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
LaurenFlew with Spirit AirlinesORD-MCOFeb 2024
If you can get by with a personal item, spirit has the best prices often at the best times to fly chicago to orlando for a weekend

FAQs for booking flights from Illinois to Florida

  • How does KAYAK find such low prices on flights from Illinois 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 Illinois to Florida.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois 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 Illinois 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 Illinois 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 Illinois 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 Illinois to Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Florida?

    Illinois and Florida are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (256 flights per week), United Airlines (227 flights per week), and Air New Zealand (206 flights per week).

  • How many airports are there in Florida?

    There are 22 airports in Florida. The busiest airport is Miami Airport (MIA), with 28% of all flights arriving there.

  • Which is the cheapest airport to fly into in Florida?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Florida is Punta Gorda Airport (PGD), with an average flight price of $100.

  • What is the cheapest day to fly to Florida?

    Based on KAYAK data, the cheapest day to fly to Florida is Tuesday where round-trip tickets can be as cheap as $254. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $307 on average.

  • 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 $239 on average. Morning departures are around 17% more expensive than evening flights, on average. The most expensive time of day to fly to Florida is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $303.

  • What is the cheapest flight to Florida?

    The cheapest ticket to Florida from Illinois found in the last 72 hours was to Tampa, at $76 round-trip. The most popular route is Bloomington (BMI) to Orlando Sanford Intl Airport (SFB) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $85.

  • What is the cheapest month to fly from Illinois to Florida?

    The cheapest month for flights from Illinois to Florida is April, when tickets cost $108 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $270 and $260 respectively.

  • How far in advance should I book a flight from Illinois to Florida?

    To get a below average price on the flight from Illinois to Florida, you should book around 2 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

  • How many cities have direct flights to Florida?

    From Illinois, there are direct flights to Florida from 6 cities. The city with the most direct flights is Chicago, with 1,838 direct flights each week.

  • How many direct flights to Florida are there each day?

    There are around 269 direct flights from within Illinois to Florida every day. Most flights (55%) depart in the morning.

  • How many direct flights to Florida are there each week?

    Each week there are around 1,878 direct flights from within Illinois to Florida. The most common day for departures is Sunday, with 16% of flights taking off on this day.

  • How long is the flight to Florida?

    An average nonstop flight from Illinois to Florida takes 3h 26m, covering a distance of 1019 miles. The shortest route is St. Louis (STL) to Pensacola (PNS) with an average flight time of 1h 45m.

  • How many long-haul flights are there to Florida each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Florida. Instead, there are 1,878 short-haul flights (up to 3 hour flight duration), with the most arriving from Chicago.

  • What are the most popular destinations in Florida?

    Based on KAYAK flight searches, the most popular destination is Orlando (22% of total searches to Florida). The next most popular destinations are Miami (18%) and Fort Lauderdale (16%). Searches for flights to Tampa (12%), to Fort Myers (9%) and to Sarasota (5%) are also popular.

Reviews of the top 5 airlines serving from Illinois to Florida

 
Need help choosing which airline to fly with from Illinois 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 4235 reviews
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

This flight never occurred because AA couldn’t get their act together.

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

The pilot would speak it was painfully load a d the crew had to know this! Maybe the were hesitant to tell him. It was just a mediocre experience and I was in Spirit first class!

My flight was cancelled last minute and I had to pay $1600 for flights, when my original flights were $300. It was a terrible experience.

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

Great! I intend to use Spirit for future flights. No complaints .

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

Better than expected. Staff were friendly and nice on both flights.

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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

Everything you need to know for your flight to Florida

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.