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$36 Find cheap flights from Florida Keys to Chicago

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 8/26. 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
Tue 7/2
Tue 7/9

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Good to know

Low season

February

High season

July

Cheapest flight

$36
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Miami to Chicago Midway 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, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 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, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 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 10410 reviews
8.0Entertainment
7.9Comfort
8.2Boarding
8.6Crew
7.4Food
Airline reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

8.0 Excellentrghinftl, May 2024FLL - BOS
Read more about Delta reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

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.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

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.

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...

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Frontier is a crappy airline nothing about it is honest

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.

Book cheap flights from Florida Keys to Chicago

Recent round-trip flight deals

8/22Thu
nonstopSpirit Airlines
3h 22mMIA-ORD
8/27Tue
nonstopSpirit Airlines
3h 14mORD-MIA
$59
8/20Tue
nonstopSpirit Airlines
3h 23mMIA-ORD
8/27Tue
nonstopSpirit Airlines
3h 16mORD-MIA
$60
6/19Wed
nonstopFrontier
3h 11mMIA-MDW
6/24Mon
nonstopFrontier
3h 07mMDW-MIA
$60
9/6Fri
nonstopFrontier
3h 10mMIA-MDW
9/23Mon
nonstopFrontier
3h 04mMDW-MIA
$61
7/4Thu
1 stopAmerican Airlines
6h 32mEYW-ORD
7/5Fri
1 stopAmerican Airlines
8h 30mORD-EYW
$198
7/9Tue
1 stopDelta
8h 02mMIA-ORD
7/16Tue
1 stopDelta
7h 38mORD-MIA
$216
7/10Wed
1 stopDelta
5h 30mMIA-MDW
7/16Tue
1 stopDelta
7h 13mMDW-MIA
$216
7/4Thu
1 stopAmerican Airlines
6h 32mEYW-ORD
7/7Sun
1 stopAmerican Airlines
8h 30mORD-EYW
$273
7/2Tue
2 stopsUnited Airlines
11h 10mEYW-ORD
7/6Sat
1 stopUnited Airlines
10h 25mORD-EYW
$420
7/1Mon
2 stopsUnited Airlines
15h 15mEYW-ORD
7/5Fri
1 stopUnited Airlines
7h 09mORD-EYW
$433

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Recent one-way flight deals

8/26Mon
nonstopFrontier
3h 10mMIA-MDW
$36
7/4Thu
nonstopFrontier
3h 16mMIA-MDW
$37
6/12Wed
1 stopSpirit Airlines
10h 34mMIA-ORD
$38
6/21Fri
nonstopSpirit Airlines
3h 29mMIA-ORD
$41
9/3Tue
nonstopAmerican Airlines
3h 26mMIA-ORD
$69
11/5Tue
1 stopDelta
7h 48mMIA-ORD
$108
8/25Sun
1 stopDelta
5h 32mMIA-MDW
$108
7/12Fri
nonstopAmerican Airlines
3h 23mMIA-ORD
$139
11/22Fri
nonstopUnited Airlines
3h 24mMIA-ORD
$187
8/12Mon
1 stopUnited Airlines
23h 01mEYW-ORD
$207

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Last minute flights from Florida Keys to Chicago

Last minute flight, train and bus deals

6/7Fri
nonstopFrontier
3h 11mMIA-MDW
6/11Tue
nonstopFrontier
3h 08mMDW-MIA
$98
6/7Fri
nonstopSpirit Airlines
3h 29mMIA-ORD
6/12Wed
multi-stopSpirit Airlines
28h 47mORD-MIA
$136
6/7Fri
nonstopSpirit Airlines
3h 29mMIA-ORD
6/11Tue
nonstopSpirit Airlines
3h 18mORD-MIA
$149
6/5Wed
nonstopFrontier
3h 11mMIA-MDW
6/12Wed
nonstopFrontier
3h 07mMDW-MIA
$152
6/5Wed
multi-stopFrontier
8h 42mMIA-MDW
6/11Tue
nonstopFrontier
3h 08mMDW-MIA
$153
6/7Fri
multi-stopFrontier
11h 02mMIA-MDW
6/11Tue
nonstopFrontier
3h 08mMDW-MIA
$154
6/3Mon
nonstopAmerican Airlines
3h 26mMIA-ORD
6/19Wed
nonstopAmerican Airlines
3h 27mORD-MIA
$454
6/3Mon
multi-stopAmerican Airlines
5h 31mMIA-ORD
6/19Wed
nonstopAmerican Airlines
3h 27mORD-MIA
$464
6/4Tue
multi-stopDelta
8h 35mMIA-MDW
6/13Thu
multi-stopDelta
6h 11mMDW-MIA
$481
6/6Thu
multi-stopDelta
5h 48mMIA-MDW
6/13Thu
multi-stopDelta
6h 11mMDW-MIA
$541

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Flights to Chicago

Return flight deals:

Chicago - Florida Keys

Cabin classes:

$360
$419
$234
$43