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Find cheap flights from Florida Keys to Illinois from $29

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Florida Keys to Illinois departing on 5/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 5/26
Sun 6/2

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Low season

January

High season

December

Cheapest flight

$29
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 6% increase in price.
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 to Illinois from Florida Keys 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 to Illinois with an airline and back to Florida Keys 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 to Illinois from Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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.
7.8
Copa AirlinesOverall score based on 2861 reviews
8.3crew
7.2entertainment
7.4food
8.1boarding
7.7comfort
Airline reviews

Captain and Crew were excellent. The Boeing 737-800 was showing its age. In flight entertainment system was sluggish and my Business Class seat on the outbound flight had some mechanical issues. Only real problem was the location of the Gate in Panama PTY. It was a 40 minute hike from Security to the Gate. There should have been some sort of warning about the distance.

10.0 ExcellentAnonymous, Mar 2024PTY - BWI
Read more about Copa Airlines reviews

Captain and Crew were excellent. The Boeing 737-800 was showing its age. In flight entertainment system was sluggish and my Business Class seat on the outbound flight had some mechanical issues. Only real problem was the location of the Gate in Panama PTY. It was a 40 minute hike from Security to the Gate. There should have been some sort of warning about the distance.

landed in panama it was in terminal one. We had to take a bus to terminal two for customs. Then back to terminal one. It was very frustrating. Then, on the way back from panama it was the same situation. We had to go back and forth between terminals to check in and drop our bags and then to board. When we were leaving, we had to wait in line for the boarding area and go through another gate security process. They told the bottles of water and coffee were bought while in line in the airport after we passed the main security. Ridiculous (and expensive). A much better communication system is needed.

This was my first time flying Copa but I'll definitely be back! Great service, professional agents, and delicious food for a fair price. Thanks for a great trip!

Horrible experience from start to end. Copa costumer service is non existent. They treat you bad. Everybody tells you different information. We didn’t received our luggage in the 1 day stop we did even we they said if was not going to be a problem. They didn’t respect the seats that we had and spread our family leaving in between of two big people who didn’t leave any space for me and crush me from side to side. I’ll never recommend Copa to anybody.

No cumpli mencionado trayecto por reasignacion de Copa Pero extraviaron mis maletas por su culpa

I was fortunate enough to have an entire row to myself and that was the highlight. Unfortunately, the flight was really turbulent which had no impact on how effective the crew was. However, I am disabled and should have boarded the flight first, but that wasn't the case. They also decided to take my bag at the gate because I had one too many and upon my picking it up at JFK it along with my rollator had been damaged. I am a vegan so the didn't have a proper meal for me and I was unable to view the entertainment because I didn't receive a set of headphones and if I needed to supply my own I wasn't made aware of that either. The crew was great, but overall everything was pretty lackluster.

LOCKED MY BAG WITHOUT CONSENT. Had to have my zippers cut upon arrival in Costa Rica.

Pros: "The seats in economy were confortable. The best thing was Copa gave us seats in the second line and my family traveled together."
Cons: "Coffe service could better the experience"
Cons: "Sure. I had booked a two week vacation in Brazil. All hotels, car rental and guides booked. Copa changed my fligjt at the last minute and out of the 14 days vacatipn I had in Brazil, they would have me spend 6 days in Panama City!!! Lost of small fortune with hotels, car rentals amd had to buy another ticket with Latam. They are a scam!!"
Cons: "Due the COVID-19 El Salvador closed its boarders, leaving me unable to fly. I have sent two emails, called and spoke to a customer service representative who treated me unprofessionally and rude. After that I have been calling numerous times with a wait of over 25 minutes each time and I still have to answer from you as a company. I am extremely disappointed and want an answer soon."

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

Flight was delayed by over an hour and gate checked bags took 15 minutes to be delivered to the jet bridge.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

I paid just under 200 for flight and luggage, then paid 200 to change the flight, then paid 100 for a carry on. Then the cancelled the flight. Of the 500 I spent they refunded 250. I bought a delta flight for 270 never flew with spirit, but spirit kept 250, not even refunding the 100 for the carry on though they cancelled the flight (for weather on a day with only a slight rain ).

Flight attendants heavily pushed their affinity credit card. Very annoying

On time and fast. Overall it was a pleasant experience.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Crew members are very rude and not cooperate with passengers.

30 minute delay due to boarding and settling of a family.

I am HIGHLY unhappy with the amount of money I spent on the flight. Paid in advance only to find the flight at a discount price a week or so before the flight. I will not fly frontier again and have bad mouthed your business since to anyone I have spoken with about flying (which has been many a people). Crew was mediocre and instead of moving me to a spot where I could gain some leg room they sat their flight attendant there. Won’t be flying frontier in the future.

Well, I didn’t have food! So NA wasn’t an option. I’ll be back!

First time flying with Frontier . From buying tickets ,getting boarding pass and boarding plane was super easy. Definitely would fly again with Frontier .

Our flight was on time and unremarkable which I'm grateful for, as it is not the norm traveling these days. Frontier is a low-cost carrier and it really shows when compared to other "normal" carriers. They don't even give you water during the flight. The coach seats are decent, however it was not as clean as it should be. We had crumbs all over the floor by our seats.

They lost my baggage on my connection flight, it’s been 24 hours since I put my claim in and still no update on my bags.

they charge too much when you arrive in the air port

The flight was canceled, then delayed twice, we were moved gates twice. Short staff at the counter and check in. We waited for our flight 9 hours. Will never use Frontier ever again, or Spirit.

The flight was delayed 1 hour. The Seats are the worst most uncomfortable chairs I have ever sat in. I have folding chairs in my Garage that are more comfortable.

Book cheap flights from Florida Keys to Illinois

Recent round-trip flight deals

5/14Tue
nonstopSpirit Airlines
3h 25mMIA-ORD
5/15Wed
nonstopSpirit Airlines
3h 17mORD-MIA
$51
5/7Tue
nonstopSpirit Airlines
3h 28mMIA-ORD
5/14Tue
1 stopSpirit Airlines
7h 46mORD-MIA
$52
5/29Wed
nonstopFrontier
3h 15mMIA-MDW
6/8Sat
nonstopFrontier
3h 09mMDW-MIA
$77
5/15Wed
nonstopFrontier
3h 32mMIA-MDW
5/17Fri
nonstopFrontier
3h 11mMDW-MIA
$81
5/15Wed
nonstopAmerican Airlines
3h 26mMIA-ORD
5/21Tue
nonstopAmerican Airlines
3h 04mORD-MIA
$179
5/21Tue
1 stopDelta
6h 17mMIA-MDW
5/29Wed
1 stopDelta
4h 32mMDW-MIA
$233
5/29Wed
1 stopDelta
5h 35mMIA-MDW
6/3Mon
1 stopDelta
6h 45mMDW-MIA
$236
8/13Tue
1 stopAmerican Airlines
6h 38mEYW-ORD
8/27Tue
1 stopAmerican Airlines
5h 48mORD-EYW
$245
9/13Fri
2 stopsUnited Airlines
21h 37mMIA-STL
9/15Sun
1 stopUnited Airlines
8h 38mSTL-MIA
$456
5/11Sat
2 stopsUnited Airlines
13h 05mEYW-ORD
5/14Tue
1 stopUnited Airlines
9h 24mORD-EYW
$463

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Recent one-way flight deals

5/21Tue
nonstopSpirit Airlines
3h 25mMIA-ORD
$29
5/15Wed
1 stopSpirit Airlines
11h 57mMIA-ORD
$32
6/11Tue
nonstopFrontier
3h 15mMIA-MDW
$40
6/11Tue
nonstopFrontier
3h 15mMIA-MDW
$42
5/15Wed
1 stopDelta
5h 05mMIA-ORD
$106
5/29Wed
1 stopDelta
5h 35mMIA-MDW
$108
6/26Wed
nonstopAmerican Airlines
3h 04mMIA-STL
$120
5/22Wed
nonstopAmerican Airlines
3h 03mMIA-STL
$127
5/15Wed
nonstopUnited Airlines
3h 30mMIA-ORD
$127
5/2Thu
nonstopUnited Airlines
3h 30mMIA-ORD
$180

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Last minute flights from Florida Keys to Illinois

Last minute flight, train and bus deals

5/1Wed
nonstopFrontier
3h 32mMIA-MDW
5/8Wed
nonstopFrontier
3h 17mMDW-MIA
$91
5/1Wed
nonstopSpirit Airlines
3h 28mMIA-ORD
5/8Wed
nonstopSpirit Airlines
3h 19mORD-MIA
$113
4/30Tue
nonstopFrontier
3h 32mMIA-MDW
5/7Tue
nonstopFrontier
3h 17mMDW-MIA
$118
5/1Wed
nonstopSpirit Airlines
3h 28mMIA-ORD
5/8Wed
multi-stopSpirit Airlines
9h 11mORD-MIA
$126
4/27Sat
nonstopAmerican Airlines
3h 27mMIA-ORD
4/27Sat
multi-stopAmerican Airlines
4h 20mORD-MIA
$286
4/27Sat
multi-stopAmerican Airlines
5h 05mMIA-ORD
4/27Sat
multi-stopAmerican Airlines
4h 20mORD-MIA
$294
4/27Sat
multi-stopDelta
5h 53mMIA-MDW
5/2Thu
multi-stopDelta
5h 53mMDW-MIA
$413
4/27Sat
multi-stopDelta
5h 10mMIA-MDW
5/8Wed
multi-stopDelta
6h 45mMDW-MIA
$423
4/29Mon
multi-stopUnited Airlines
5h 49mMIA-STL
5/6Mon
multi-stopUnited Airlines
13h 37mSTL-MIA
$760
4/27Sat
multi-stopUnited Airlines
5h 49mMIA-STL
4/28Sun
multi-stopUnited Airlines
13h 37mSTL-MIA
$829

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Flights to Illinois

Return flight deals:

Illinois - Florida Keys

Cabin classes:

$274
$293
$217
$38