Find flights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

Find cheap flights from Florida Keys to Chicago from $26

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago 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
พ. 6/5
พ. 6/12

Search hundreds of travel sites at once for deals on flights to Chicago

In the last 7 days travelers have searched 42,573,820 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

February

High season

July

Cheapest flight

$26
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from Miami to Chicago O'Hare Airport

FAQs for booking flights from Florida Keys to Chicago

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

    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 Chicago.

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

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

    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 Chicago 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 Chicago?

    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 Chicago 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

Prefer to fly non-stop from Florida Keys to Chicago?

Find which airlines fly direct from Florida Keys to Chicago, which days they fly and book direct flights.

Nonstop departures

Florida Keys to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Florida Keys

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 5 airlines serving from Florida Keys to Chicago

 
Need help choosing which airline to fly with from Florida Keys to Chicago? 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
DeltaOverall score based on 10818 reviews
8.2Boarding
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
Airline reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

6.0 GoodJames, Apr 2024TPA - RDU
Read more about Delta reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Flight was great. DELTA did a fantastic job! FLL airport was chaotic!

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.

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.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The CX617 from HK to BKK was delayed more than 1.5 hours.

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.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

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

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

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 Chicago

Recent round-trip flight deals

5/22พ.
nonstopSpirit Airlines
3h 25mMIA-ORD
5/29พ.
nonstopSpirit Airlines
3h 17mORD-MIA
$33
5/22พ.
nonstopSpirit Airlines
3h 25mMIA-ORD
5/29พ.
nonstopSpirit Airlines
3h 17mORD-MIA
$40
5/22พ.
nonstopFrontier
3h 15mMIA-MDW
5/29พ.
nonstopFrontier
3h 11mMDW-MIA
$40
5/22พ.
nonstopFrontier
3h 15mMIA-MDW
5/29พ.
nonstopFrontier
3h 11mMDW-MIA
$43
5/22พ.
1 stopDelta
5h 35mMIA-MDW
5/29พ.
1 stopDelta
7h 08mMDW-MIA
$216
7/9อ.
1 stopDelta
4h 50mMIA-MDW
7/15จ.
1 stopDelta
5h 10mMDW-MIA
$232
6/7ศ.
2 stopsAmerican Airlines
8h 12mEYW-ORD
6/10จ.
1 stopAmerican Airlines
5h 44mORD-EYW
$470
7/20ส.
1 stopUnited Airlines
6h 20mEYW-ORD
7/20ส.
2 stopsUnited Airlines
10h 07mORD-EYW
$517
7/20ส.
1 stopAmerican Airlines
6h 05mEYW-ORD
7/20ส.
1 stopAmerican Airlines
14h 25mORD-EYW
$756
6/12พ.
1 stopUnited Airlines
8h 55mEYW-ORD
6/19พ.
1 stopUnited Airlines
6h 35mORD-EYW
$1,021

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/21อ.
1 stopSpirit Airlines
8h 39mMIA-ORD
$26
6/11อ.
nonstopSpirit Airlines
3h 26mMIA-ORD
$29
6/12พ.
nonstopFrontier
3h 11mMIA-MDW
$29
6/6พฤ.
nonstopFrontier
3h 16mMIA-MDW
$30
6/4อ.
1 stopDelta
5h 48mMIA-MDW
$108
6/6พฤ.
1 stopDelta
5h 35mMIA-MDW
$124
8/9ศ.
nonstopAmerican Airlines
3h 26mMIA-ORD
$142
6/28ศ.
nonstopAmerican Airlines
3h 23mMIA-ORD
$147
7/29จ.
1 stopUnited Airlines
23h 01mEYW-ORD
$203
9/13ศ.
1 stopUnited Airlines
28h 05mEYW-ORD
$225

Search by stops

Search by airline

Search by price

Last minute flights from Florida Keys to Chicago

Last minute flight, train and bus deals

5/11ส.
multi-stopSpirit Airlines
13h 18mMIA-ORD
5/15พ.
nonstopSpirit Airlines
3h 19mORD-MIA
$69
5/11ส.
nonstopFrontier
3h 33mMIA-MDW
5/15พ.
nonstopFrontier
3h 17mMDW-MIA
$109
5/8พ.
nonstopFrontier
3h 32mMIA-MDW
5/12อา.
nonstopFrontier
3h 17mMDW-MIA
$118
5/11ส.
multi-stopSpirit Airlines
13h 18mMIA-ORD
5/15พ.
multi-stopSpirit Airlines
12h 57mORD-MIA
$119
5/11ส.
multi-stop
13h 18mMIA-ORD
5/13จ.
multi-stop
10h 36mORD-MIA
$128
5/8พ.
multi-stopDelta
5h 48mMIA-MDW
5/15พ.
multi-stopDelta
7h 00mMDW-MIA
$327
5/11ส.
multi-stopDelta
5h 55mMIA-MDW
5/16พฤ.
multi-stopDelta
6h 45mMDW-MIA
$353
5/11ส.
multi-stopUnited Airlines
13h 05mEYW-ORD
5/14อ.
multi-stopUnited Airlines
9h 24mORD-EYW
$493
5/11ส.
multi-stopUnited Airlines
13h 05mEYW-ORD
5/14อ.
multi-stopUnited Airlines
8h 25mORD-EYW
$548
5/10ศ.
multi-stopVolaris
17h 41mMIA-MDW
5/17ศ.
multi-stopVolaris
16h 10mMDW-MIA
$876

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Florida Keys

Cabin classes:

$333
$301
$219
$38