$59 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 10/13. 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.
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1 adult, Economy

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Cheap Flights from Florida Keys to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Florida Keys to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Florida Keys to Chicago

Fri, Oct 10 - Sat, Oct 11
Spirit Airlines Logo
7:00 am - 9:22 amMIA-ORD
3h 22mnonstop
Spirit Airlines Logo
9:27 am - 1:30 pmORD-MIA
3h 03mnonstop
$107Spirit Airlines
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Thu, Oct 2 - Sat, Oct 4
Spirit Airlines Logo
7:00 am - 9:18 amMIA-ORD
3h 18mnonstop
Spirit Airlines Logo
10:27 am - 2:39 pmORD-MIA
3h 12mnonstop
$108Spirit Airlines
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Wed, Nov 19 - Tue, Dec 2
Spirit Airlines Logo
10:15 am - 12:30 pmMIA-ORD
3h 15mnonstop
Spirit Airlines Logo
1:35 pm - 5:50 pmORD-MIA
3h 15mnonstop
$109Spirit Airlines
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Fri, Oct 10 - Tue, Oct 14
Frontier Logo
9:10 am - 11:27 amMIA-MDW
3h 17mnonstop
Frontier Logo
8:05 am - 2:32 pmMDW-MIA
5h 27m1 stop
$120Frontier
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Fri, Oct 17 - Mon, Oct 20
Frontier Logo
8:00 am - 3:12 pmMIA-MDW
8h 12m1 stop
Frontier Logo
10:33 am - 2:33 pmMDW-MIA
3h 00mnonstop
$121Frontier
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Wed, Oct 22 - Sun, Oct 26
American Airlines Logo
8:40 am - 11:03 amMIA-ORD
3h 23mnonstop
American Airlines Logo
6:00 am - 10:06 amORD-MIA
3h 06mnonstop
$157American Airlines
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Thu, Oct 16 - Mon, Oct 20
Southwest Logo
11:50 am - 1:55 pmMIA-MDW
3h 05mnonstop
Southwest Logo
8:10 am - 12:10 pmMDW-MIA
3h 00mnonstop
$157Southwest
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Sat, Nov 8 - Tue, Nov 11
United Airlines Logo
4:00 pm - 6:46 pmEYW-ORD
3h 46mnonstop
United Airlines Logo
6:02 am - 2:04 pmORD-EYW
7h 02m1 stop
$305United Airlines
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Sat, Nov 8 - Tue, Nov 11
American Airlines Logo
1:08 pm - 3:48 pmEYW-ORD
3h 40mnonstop
American Airlines Logo
9:03 am - 1:36 pmORD-EYW
3h 33mnonstop
$327American Airlines
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Mon, Nov 24 - Sat, Nov 29
United Airlines Logo
3:00 pm - 9:16 pmEYW-ORD
7h 16m1 stop
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
$339United Airlines
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Everything you should know

Cheapest round-trip
$107
Overall average: $215
Spirit Airlines
Fri 10/10Sat 10/11
MIA - ORD • Non-stop
Cheapest one-way
$59
Typical prices: $106-269
Spirit Airlines
Mon 10/13
MIA - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 4% lower on average.
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.

Reviews of the 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
SouthwestOverall score based on 4242 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

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

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

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.

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

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

I will use spirit more New clean aircraft Excellent crew ! Quick boarding process !

The flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

For the minimalist experience, it is really a great ride-- feels a little like public transport i guess

I didn’t mind being delayed due to weather, but continuing to post (and not update) that we would be delayed until after the flight was already supposed to have taken off was a bit much. In the future, please announce the delay even if the time is still unknown.

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

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.

Traveling to a place near Chicago?

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Florida Keys

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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