$47 Find Cheap Flights from Florida Keys to Illinois

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Low seasonJanuary
High seasonMay
Cheapest flight$47
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 10% 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 $374.

  • 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 $978 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 15% 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 $294 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 $294.

  • 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 5 weeks before departure.

  • How long is the flight to Illinois?

    An average nonstop flight from Florida Keys to Illinois takes 9h 04m, covering a distance of 1183 miles. The shortest route is Miami (MIA) to St. Louis (STL) with an average flight time of 2h 49m.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (96% of total searches to Illinois). The next most popular destinations are Peoria (2%) and Moline (1%). Searches for flights to Bloomington (1%) 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 4294 reviews
8.2Boarding
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
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.

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

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

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.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

I paid for streaming wifi and the connection was poor.

We had an 8 hr delay so it was not good

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Easy boarding. Met expectations for a 2-3 hour flight. Early arrival at DFW caused a 39 minute delay on the tarmac in getting to our gate. 😏 overall, good flight.

Very efficient process and boarding, seats felt standard. Flight conditions from take off to landing had been very smooth. Alcohol on the menu however was not available… Will fly Spirit in the future for the price, you can’t really complain if you fly light.

Bad experience. Unhappy with the changing of flight times and one particular flight attendant (Bartholomew) on our flight from Orlando to Detroit. Traveling with a large family of 7, including our 18 month old, can be arduous but when the airline changes your flight time from landing at 9:30 pm to landing after midnight, this becomes much more difficult. When our 18 month old was predictably over tired and fussy, my wife and I tried to move to an open row so we can console her more effectively. The flight attendent rebuked us and said we could not sit in an exit row. We were not planning on sitting there for more than a few minutes but just to have space to console our screaming 18 month old. Spirit did not allow for a family friendly trip. Likely will be choosing a different airline next time.

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

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Book cheap flights from Florida Keys to Illinois

Recent round-trip flight deals

5/28Wed
nonstopSpirit Airlines
3h 26mMIA-ORD
6/4Wed
nonstopSpirit Airlines
3h 15mORD-MIA
$71
5/28Wed
nonstopSpirit Airlines
3h 26mMIA-ORD
6/1Sun
nonstopSpirit Airlines
3h 13mORD-MIA
$72
7/2Wed
nonstopSouthwest
3h 10mMIA-MDW
7/5Sat
nonstopSouthwest
3h 00mMDW-MIA
$179
5/30Fri
nonstopSouthwest
3h 10mMIA-MDW
6/3Tue
nonstopSouthwest
2h 55mMDW-MIA
$197
5/29Thu
nonstopAmerican Airlines
3h 32mMIA-ORD
6/1Sun
nonstopAmerican Airlines
3h 08mORD-MIA
$199
5/29Thu
1 stopFrontier
25h 19mMIA-MDW
6/2Mon
1 stopFrontier
24h 00mMDW-MIA
$205
5/31Sat
1 stopFrontier
22h 40mMIA-ORD
6/2Mon
1 stopFrontier
12h 24mORD-MIA
$208
7/2Wed
nonstopAmerican Airlines
3h 30mMIA-ORD
7/4Fri
nonstopAmerican Airlines
3h 07mORD-MIA
$212
6/10Tue
1 stopUnited Airlines
6h 25mMIA-STL
6/14Sat
2 stopsUnited Airlines
9h 52mSTL-MIA
$342
6/24Tue
1 stopUnited Airlines
6h 25mMIA-STL
6/25Wed
1 stopUnited Airlines
6h 19mSTL-MIA
$400

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Recent one-way flight deals

9/20Sat
nonstopSpirit Airlines
3h 26mMIA-ORD
$47
5/24Sat
nonstopSpirit Airlines
3h 26mMIA-ORD
$48
7/1Tue
nonstopAmerican Airlines
3h 34mMIA-ORD
$90
7/2Wed
nonstopSouthwest
3h 10mMIA-MDW
$90
5/11Sun
1 stopFrontier
28h 09mMIA-STL
$97
6/7Sat
1 stopFrontier
5h 52mMIA-ORD
$98
6/25Wed
nonstopAmerican Airlines
3h 31mMIA-ORD
$99
5/30Fri
nonstopSouthwest
3h 10mMIA-MDW
$99
5/20Tue
nonstopUnited Airlines
3h 34mMIA-ORD
$100
6/2Mon
1 stopUnited Airlines
26h 22mEYW-ORD
$173

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Last minute flights from Florida Keys to Illinois

Last minute flight, train and bus deals

5/4Sun
multi-stop
18h 41mMIA-ORD
5/6Tue
nonstop
3h 12mORD-MIA
$197
5/1Thu
multi-stopFrontier
10h 07mMIA-STL
5/3Sat
multi-stopFrontier
8h 07mSTL-MIA
$208
5/5Mon
nonstopSpirit Airlines
3h 33mMIA-ORD
5/20Tue
nonstopSpirit Airlines
3h 15mORD-MIA
$212
5/5Mon
nonstopSpirit Airlines
3h 33mMIA-ORD
5/17Sat
nonstopSpirit Airlines
3h 15mORD-MIA
$246
5/5Mon
multi-stopSouthwest
6h 10mMIA-MDW
5/5Mon
nonstopSouthwest
2h 55mMDW-MIA
$399
5/5Mon
multi-stopSouthwest
6h 10mMIA-MDW
5/7Wed
multi-stopSouthwest
5h 55mMDW-MIA
$409
5/4Sun
nonstopAmerican Airlines
3h 04mMIA-STL
5/5Mon
nonstopAmerican Airlines
2h 46mSTL-MIA
$489
5/4Sun
nonstopAmerican Airlines
3h 04mMIA-STL
5/5Mon
multi-stopAmerican Airlines
4h 57mSTL-MIA
$499
5/4Sun
nonstopUnited Airlines
3h 34mMIA-ORD
5/7Wed
nonstopUnited Airlines
3h 18mORD-MIA
$567
5/4Sun
multi-stopUnited Airlines
7h 00mMIA-ORD
5/7Wed
nonstopUnited Airlines
3h 18mORD-MIA
$577

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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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