$26 Find Cheap Flights from Illinois to Florida

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Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$26
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to Fort Myers

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 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 Tampa Airport (TPA), with an average flight price of $139.

  • 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 $253. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $320 on average.

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

    The cheapest time of day to fly to Florida is generally in the evening, when round-trip flights cost $239 on average. Morning departures are around 25% 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 $310.

  • What is the cheapest flight to Florida?

    The cheapest ticket to Florida from Illinois found in the last 72 hours was to Orlando Sanford Intl Airport, at $79 round-trip. The most popular route is Belleville (BLV) to Orlando Sanford Intl Airport (SFB) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $79.

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

    The cheapest month for flights from Illinois to Florida is January, when tickets cost $98 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $250 and $248 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. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

  • How long is the flight to Florida?

    An average nonstop flight from Illinois to Florida takes 3h 17m, covering a distance of 992 miles. The shortest route is St. Louis (STL) to Pensacola (PNS) with an average flight time of 1h 40m.

  • What are the most popular destinations in Florida?

    Based on KAYAK flight searches, the most popular destination is Orlando (21% of total searches to Florida). The next most popular destinations are Tampa (17%) and Miami (16%). Searches for flights to Fort Lauderdale (16%), to Fort Myers (7%) and to Sarasota (4%) 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 4244 reviews
7.0Food
7.6Entertainment
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

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

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

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!

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.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Smooth flight, especially take off and landing, and great crew on board. Really loved the stroopwaffles!

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

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.

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

The boarding was pretty easy. However, the first class seats are not lay flat as other airlines (like JetBlue) has and therefore sleeping was a challenge.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Would have thought that they would gas up plane before everyone got on board

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Standard. No different than a discount carrier on a short trip.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

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 😩

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.

you guys canceled my flight last minute and lost my luggage.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

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.

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.

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!

Book cheap flights from Illinois to Florida

Recent round-trip flight deals

8/5Tue
nonstopSpirit Airlines
2h 55mORD-RSW
8/12Tue
nonstopSpirit Airlines
3h 10mRSW-ORD
$77
8/5Tue
nonstopSpirit Airlines
2h 55mORD-RSW
8/8Fri
nonstopSpirit Airlines
3h 10mRSW-ORD
$78
10/19Sun
nonstopFrontier
2h 39mMDW-TPA
10/26Sun
nonstopFrontier
2h 49mTPA-MDW
$102
9/4Thu
nonstopFrontier
2h 50mORD-TPA
9/7Sun
nonstopFrontier
3h 02mTPA-ORD
$105
9/1Mon
nonstopUnited Airlines
3h 17mORD-MIA
9/5Fri
nonstopUnited Airlines
3h 28mMIA-ORD
$137
9/4Thu
nonstopSouthwest
3h 00mMDW-MIA
9/7Sun
nonstopSouthwest
3h 05mMIA-MDW
$137
8/17Sun
nonstopAmerican Airlines
3h 07mORD-MIA
8/22Fri
nonstopAmerican Airlines
3h 31mMIA-ORD
$145
8/17Sun
nonstopSouthwest
3h 00mMDW-MIA
8/24Sun
nonstopSouthwest
3h 05mMIA-MDW
$145
8/5Tue
nonstopAmerican Airlines
2h 50mORD-TPA
8/12Tue
nonstopAmerican Airlines
3h 06mTPA-ORD
$157
9/13Sat
nonstopUnited Airlines
3h 03mORD-RSW
9/20Sat
nonstopUnited Airlines
3h 15mRSW-ORD
$157

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Recent one-way flight deals

8/5Tue
nonstopSpirit Airlines
2h 55mORD-RSW
$26
8/5Tue
nonstopSpirit Airlines
2h 55mORD-RSW
$30
10/19Sun
nonstopFrontier
2h 44mORD-TPA
$43
10/19Sun
nonstopFrontier
2h 39mMDW-TPA
$43
9/7Sun
nonstopAmerican Airlines
3h 08mORD-MIA
$68
8/31Sun
nonstopAmerican Airlines
3h 02mORD-MIA
$69
9/25Thu
nonstopSouthwest
3h 00mMDW-MIA
$69
8/11Mon
nonstopSouthwest
3h 00mMDW-MIA
$77
11/16Sun
nonstopUnited Airlines
3h 06mORD-RSW
$80
9/23Tue
1 stopUnited Airlines
7h 22mORD-FLL
$84

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Last minute flights from Illinois to Florida

Last minute flight, train and bus deals

7/15Tue
multi-stopFrontier
8h 11mMDW-MCO
7/22Tue
multi-stopFrontier
4h 55mMCO-MDW
$146
7/19Sat
nonstopFrontier
2h 52mORD-TPA
7/26Sat
nonstopFrontier
3h 16mTPA-ORD
$153
7/18Fri
nonstopSpirit Airlines
2h 47mORD-MCO
7/23Wed
nonstopSpirit Airlines
3h 08mMCO-ORD
$161
7/19Sat
nonstopSpirit Airlines
2h 55mORD-RSW
7/31Thu
nonstopSpirit Airlines
3h 10mRSW-ORD
$164
7/19Sat
nonstopAmerican Airlines
2h 56mORD-PBI
7/29Tue
nonstopAmerican Airlines
3h 17mPBI-ORD
$278
7/19Sat
multi-stopAmerican Airlines
7h 22mORD-PBI
7/29Tue
nonstopAmerican Airlines
3h 17mPBI-ORD
$288
7/18Fri
multi-stopSouthwest
6h 10mMDW-MIA
8/4Mon
nonstopSouthwest
3h 10mMIA-MDW
$327
7/18Fri
multi-stopSouthwest
8h 05mORD-PBI
7/26Sat
multi-stopSouthwest
5h 50mPBI-ORD
$365
7/16Wed
multi-stopUnited Airlines
8h 58mORD-PBI
7/19Sat
multi-stopUnited Airlines
16h 10mPBI-ORD
$535
7/15Tue
multi-stopUnited Airlines
7h 40mORD-PBI
7/19Sat
multi-stopUnited Airlines
14h 32mPBI-ORD
$585

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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.

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