$58 Find Cheap Flights from Florida Keys to Illinois

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Low seasonJanuary
High seasonAugust
Cheapest flight$58
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 15% 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 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 $303.

  • 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 $329. 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 $353 on average. Morning departures are around 16% 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 $399 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 $399.

  • 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 $684 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. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

  • How long is the flight to Illinois?

    An average nonstop flight from Florida Keys to Illinois takes 9h 28m, covering a distance of 1183 miles. The shortest route is Miami (MIA) to St. Louis (STL) with an average flight time of 2h 45m.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (99% of total searches to Illinois). The next most popular destinations are Moline (1%) and Peoria (0%). Searches for flights to Bloomington (0%) are also popular.

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 4278 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

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.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

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.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

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

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

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.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

The flight was canceled and was bounced around time wise with my elderly parents. That being said the gentleman in custody service was amazingly helpful

It amaze me how other airlines leave on time and Spirit always have some type of delay. I’ve flown with Spirit many times, but it reached a point I’d rather pay twice the amount and not deal with this corporation they never do nothing to reimburse people for their time or headaches.

Easy boarding and good flight. Need to work on the beverage and snack situation

Spirit charges you to breathe in their presence. They have you pick and buy your seat in advance and then I got bumped from the seat I paid for because THEY overbooked the flight by a dozen people. they do not provide any entertainment, they do not provide even a small cup of water - you have to pay for everything. I will never fly Spirit again.

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.

The seats! Do not nickel and dime! Be transparent about all your fees!

Not great. Overpriced and charge you for everything. All but breathing was an extra charge. Never again! Oh if you didn’t check a carry on, you couldn’t use the overhead bins. Crew said those spaces were not available. Personal items MUST go on floor. Yet, there was only 50% capacity at best! So ridiculous.

why's KAYAK involved? why'd Spirit charge me $19.72 on Apr 28 and $4.49 on May 1 ? And ironically my credit card had to be cancelled after trip due to a bogus charge, wonder if using it on the plane enabled a scammer to get it.

why's KAYAK involved? why'd Spirit charge me $19.72 on Apr 28 and $4.49 on May 1 ?

It was fine, Can’t blame you about airport issues.

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,

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Asked for a seat change to be w my wife at the gate they were great in sorting it out to make it happen

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

Book cheap flights from Florida Keys to Illinois

Recent round-trip flight deals

6/28Sat
nonstopSpirit Airlines
3h 36mMIA-ORD
7/8Tue
nonstopSpirit Airlines
3h 17mORD-MIA
$105
7/2Wed
nonstopSpirit Airlines
3h 36mMIA-ORD
7/8Tue
nonstopSpirit Airlines
3h 17mORD-MIA
$108
9/18Thu
nonstopAmerican Airlines
3h 27mMIA-ORD
9/21Sun
nonstopAmerican Airlines
3h 05mORD-MIA
$137
8/12Tue
1 stopSouthwest
7h 45mMIA-MDW
8/21Thu
nonstopSouthwest
3h 00mMDW-MIA
$157
8/14Thu
nonstopAmerican Airlines
3h 32mMIA-ORD
8/18Mon
nonstopAmerican Airlines
3h 08mORD-MIA
$158
8/12Tue
2 stopsSouthwest
8h 30mMIA-MDW
8/21Thu
nonstopSouthwest
3h 00mMDW-MIA
$162
10/9Thu
nonstopFrontier
3h 15mMIA-MDW
10/13Mon
nonstopFrontier
3h 00mMDW-MIA
$170
10/9Thu
nonstopFrontier
3h 15mMIA-MDW
10/13Mon
nonstopFrontier
3h 00mMDW-MIA
$174
7/15Tue
nonstopUnited Airlines
3h 34mMIA-ORD
7/16Wed
nonstopUnited Airlines
3h 20mORD-MIA
$257
7/4Fri
nonstopUnited Airlines
3h 34mMIA-ORD
7/11Fri
nonstopUnited Airlines
3h 20mORD-MIA
$260

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Recent one-way flight deals

7/12Sat
nonstopSpirit Airlines
3h 36mMIA-ORD
$58
7/2Wed
nonstopSpirit Airlines
3h 36mMIA-ORD
$59
9/15Mon
nonstopUnited Airlines
3h 30mMIA-ORD
$69
9/7Sun
nonstopSouthwest
3h 05mMIA-MDW
$69
10/24Fri
nonstopAmerican Airlines
3h 33mMIA-ORD
$70
8/5Tue
nonstopUnited Airlines
3h 34mMIA-ORD
$79
9/15Mon
1 stopSouthwest
5h 55mMIA-MDW
$79
9/4Thu
nonstopAmerican Airlines
2h 50mMIA-STL
$87
7/2Wed
1 stopFrontier
18h 59mMIA-ORD
$96
10/9Thu
nonstopFrontier
3h 15mMIA-MDW
$97

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Last minute flights from Florida Keys to Illinois

Last minute flight, train and bus deals

6/21Sat
nonstopSpirit Airlines
3h 36mMIA-ORD
6/28Sat
nonstopSpirit Airlines
3h 17mORD-MIA
$163
6/19Thu
multi-stopFrontier
10h 14mMIA-ORD
6/24Tue
multi-stopFrontier
11h 14mORD-MIA
$180
6/21Sat
multi-stopFrontier
10h 35mMIA-ORD
6/24Tue
multi-stopFrontier
5h 27mORD-MIA
$190
6/20Fri
nonstopSpirit Airlines
3h 36mMIA-ORD
6/24Tue
nonstopSpirit Airlines
3h 17mORD-MIA
$200
6/21Sat
nonstopSouthwest
3h 05mMIA-MDW
6/24Tue
nonstopSouthwest
3h 05mMDW-MIA
$337
6/21Sat
nonstopSouthwest
3h 05mMIA-MDW
6/23Mon
multi-stopSouthwest
6h 10mMDW-MIA
$347
6/18Wed
multi-stopAmerican Airlines
5h 36mEYW-ORD
6/24Tue
multi-stopAmerican Airlines
5h 47mORD-EYW
$371
6/20Fri
multi-stopAmerican Airlines
6h 02mMIA-MLI
6/28Sat
multi-stopAmerican Airlines
6h 07mMLI-MIA
$409
6/18Wed
multi-stopUnited Airlines
7h 29mMIA-STL
6/24Tue
multi-stopUnited Airlines
7h 44mSTL-MIA
$658
6/18Wed
multi-stopUnited Airlines
9h 53mMIA-STL
6/21Sat
multi-stopUnited Airlines
8h 11mSTL-MIA
$668

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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.

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