$42 Find Cheap Flights from Florida Keys to Illinois

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

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.

Useful Info

Good to know

Low seasonJanuary
Cheapest flight$42
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Miami to Chicago O'Hare Airport

FAQs for booking flights from Florida Keys to Illinois

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Florida Keys 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 Keys 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 Keys 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 Keys 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 Keys 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 Keys and Illinois are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (57 flights per week), Alaska Airlines (38 flights per week), and Aer Lingus (35 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 92% 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 O'Hare Intl Airport (ORD), with an average flight price of $498.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $343. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $939 on average.

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

    The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost $359 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $507.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Florida Keys found in the last 72 hours was to Chicago O'Hare Intl Airport, at $344 round-trip. The most popular route is Key West (EYW) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $344.

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

    The cheapest month for flights from Florida Keys to Illinois is December, when tickets cost $224 (return) on average. On the other hand, the most expensive months are March and April, when the average cost of round-trip tickets is $677 and $581 respectively.

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

    To get a below average price on the flight from Florida Keys to Illinois, you should book around 2 weeks before departure, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

  • How many cities have direct flights to Illinois?

    From Florida Keys, there are direct flights to Illinois from 2 cities. The city with the most direct flights is Miami, with 345 direct flights each week.

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

    There are around 50 direct flights from within Florida Keys to Illinois every day. Most flights (49%) depart in the afternoon.

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

    Each week there are around 347 direct flights from within Florida Keys to Illinois. The most common day for departures is Saturday, with 15% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Florida Keys to Illinois takes 6h 24m, covering a distance of 1183 miles. The shortest route is Miami (MIA) to St. Louis (STL) with an average flight time of 2h 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 347 short-haul flights (up to 3 hour flight duration), with the most arriving from Miami.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (98% of total searches to Illinois). The next most popular destinations are Peoria (2%) and Moline (1%). Searches for flights to Bloomington (0%) are also popular.

Reviews of the top 5 airlines serving from Florida Keys to Illinois

 
Need help choosing which airline to fly with from Florida Keys 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 4241 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

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

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

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.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

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

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

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.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

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!

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

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.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

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.

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

Flight was on time and was not crowded. Flight attendants were very understanding of my wife’s back problems.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

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

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

They switched my flight to Spirit, Never using Kayak again,

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Florida Keys

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

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