$50 Find Cheap Flights from Florida to Illinois

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Low seasonJanuary
Cheapest flight$50
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Orlando to Chicago O'Hare Airport

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

Insights shared by verified travelers who flew the route from Florida to Illinois 
Verified travelerFlew with Air CanadaJAX-ORDApr 2025
Chicago is a huge airport, wear comfortable shoes if you're looking to make a connection. It might be a 15 minute speed walk. Jacksonville is a little more compact and easier to navigate. Lots of food and beverage options in each.
CindyFlew with SouthwestTPA-MDWMar 2024
Don’t check a bag. Chicago takes forever to get your baggage.

FAQs for booking flights from Florida to Illinois

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

    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 Florida to Illinois.

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

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

    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 Florida to Illinois 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 Florida to Illinois?

    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 Florida to Illinois 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 Illinois?

    Florida and Illinois are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (246 flights per week), United Airlines (204 flights per week), and Southwest (171 flights per week).

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 91% of all flights arriving there.

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

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago Greater Rockford Airport (RFD), with an average flight price of $56.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Friday where round-trip tickets can be as cheap as $284. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $477 on average.

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

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $314 on average. Morning departures are around 18% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $382.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Florida found in the last 72 hours was to Chicago Midway Airport, at $54 round-trip. The most popular route is Fort Lauderdale (FLL) to Chicago Midway Airport (MDW) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $54.

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

    The cheapest month for flights from Florida to Illinois is July, when tickets cost $105 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $302 and $239 respectively.

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

    To get a below average price on the flight from Florida to Illinois, you should book around 2 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

  • How many cities have direct flights to Illinois?

    From Florida, there are direct flights to Illinois from 13 cities. The city with the most direct flights is Orlando, with 470 direct flights each week.

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

    There are around 266 direct flights from within Florida to Illinois every day. Most flights (52%) depart in the morning.

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

    Each week there are around 1,856 direct flights from within Florida to Illinois. The most common day for departures is Sunday, with 17% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Florida to Illinois takes 3h 29m, covering a distance of 969 miles. The shortest route is Pensacola (PNS) to St. Louis (STL) with an average flight time of 1h 50m.

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

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Illinois. Instead, there are 1,856 short-haul flights (up to 3 hour flight duration), with the most arriving from Orlando.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (87% of total searches to Illinois). The next most popular destinations are St. Louis (10%) and Peoria (1%). Searches for flights to Moline (1%), to Bloomington (0%) and to Evansville (0%) are also popular.

Reviews of the top 5 airlines serving from Florida to Illinois

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

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

10.0 ExcellentMelissa, Sep 2025MSY - MDW
Read more Southwest reviews

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

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.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Florida

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

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