$46 Find Cheap Flights from Chicago to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Florida Keys departing on 4/25. 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
1 adult, Economy, 0 bags

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida Keys.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida Keys.
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Cheap Flights from Chicago to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miaminonstop$94
Key West
Key West1 stop$309
Miami
Miaminonstop$94
Key West
Key West1 stop$309

Book Cheap Chicago to Florida Keys Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Florida Keys 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 Chicago to Florida Keys

Thu, May 7 - Sun, May 10
Frontier Logo
3:52 pm - 8:11 pm
ORD
-
MIA
3h 19mnonstop
Frontier Logo
9:21 pm - 11:59 pm
MIA
-
ORD
3h 38mnonstop
$94Frontier
Mon, Apr 20 - Thu, Apr 23
Frontier Logo
4:58 pm - 9:17 pm
ORD
-
MIA
3h 19mnonstop
Frontier Logo
9:21 pm - 11:59 pm
MIA
-
ORD
3h 38mnonstop
$99Frontier
Sat, Apr 4 - Thu, Apr 9
Spirit Airlines Logo
4:51 pm - 8:57 pm
ORD
-
MIA
3h 06mnonstop
Spirit Airlines Logo
7:20 am - 9:50 am
MIA
-
ORD
3h 30mnonstop
$100Spirit Airlines
Thu, Apr 9 - Thu, Apr 16
Multiple Airlines Logo
6:40 am - 10:59 am
ORD
-
MIA
3h 19mnonstop
Multiple Airlines Logo
10:41 am - 1:05 pm
MIA
-
ORD
3h 24mnonstop
$101Multiple Airlines
Fri, Apr 3 - Thu, Apr 9
Multiple Airlines Logo
4:51 pm - 8:57 pm
ORD
-
MIA
3h 06mnonstop
Multiple Airlines Logo
12:04 pm - 2:42 pm
MIA
-
ORD
3h 38mnonstop
$102Multiple Airlines
Sat, Apr 25 - Thu, Apr 30
Frontier Logo
3:52 pm - 8:11 pm
ORD
-
MIA
3h 19mnonstop
Frontier Logo
9:21 pm - 11:59 pm
MIA
-
ORD
3h 38mnonstop
$103Frontier
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:04 pm - 10:58 pm
ORD
-
EYW
6h 54m
1 stop
American Airlines Logo
2:12 pm - 10:47 pm
EYW
-
ORD
9h 35m
1 stop
$309American Airlines
Fri, Apr 3 - Tue, Apr 7
Spirit Airlines Logo
5:05 am - 1:37 pm
ORD
-
EYW
7h 32m
1 stop
Spirit Airlines Logo
12:25 pm - 11:17 am
EYW
-
ORD
23h 52m
1 stop
$313Spirit Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
1:50 pm - 6:16 pm
ORD
-
EYW
3h 26mnonstop
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
$319American Airlines
Tue, May 12 - Tue, May 19
Delta Logo
12:51 pm - 7:49 pm
MDW
-
EYW
5h 58m
1 stop
Delta Logo
7:30 am - 11:56 am
EYW
-
MDW
5h 26m
1 stop
$354Delta
Booking Insights

KAYAK's insights & trends for Chicago to Florida Keys flights

Get data-powered insights and trends into flights from Chicago to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Florida Keys flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Florida Keys from Chicago found in the last 72 hours was to Key West, at $249 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Key West (EYW), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $249.

What is the cheapest time of day to fly to Florida Keys?

The average price for all round-trip flights from Chicago to Florida Keys depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $285 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the morning, which is peak travel time and where the average cost of a ticket is $399.

Can I save money by flying with a layover from Chicago to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $415, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Florida Keys, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Florida Keys is September, when tickets cost $202 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $342 and $329 respectively.

What’s the cheapest day of the week to fly from Chicago to Florida Keys?

The average price of all round-trip flights from Chicago to Florida Keys clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Florida Keys, you should consider leaving on a Monday and avoid Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Mondays.

How far in advance should I book a flight from Chicago to Florida Keys?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Florida Keys, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Florida Keys, you should book around 2 weeks before departure, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$46
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago O'Hare Airport to Miami

FAQs - booking Florida Keys flights

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

    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 Chicago to Florida Keys.

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

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

    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 Chicago to Florida Keys 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 Chicago to Florida Keys?

    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 Chicago to 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 Chicago to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Florida Keys. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Florida Keys? 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 4318 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Everything is an additional fee. No one said anything when I checking in and got my boarding pass about my small carry on suitcase. Charged me $100 at the gate for that little bag that I still had to take with me. Delays for both flights for no reason and then when I asked everyone said something different. Never flying spirit again. If it was just one thing maybe. This was a show from the minute I got to the airport.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

The bag situation was confusing. I didn’t know I had to pay for Carry ons. The seats were uncomfortable and there was no entertainment

It was terrible. I had to pay again once I got to the airport because they said they never received the payment.

bought basic spirit fares, add checked bags - like the up front info on website about this. bring your own snacks, buy a soda after TSA security to bring with you, or buy on the plane (limited selection) all in all, a good experience

4 hour delay, 2 hours in the airport and then 2 hours on the tarmac. With a flight full of kids it would have been better to leave us in the airport for the delay, it was crying kids chaos on the flight. Miserable. And no apology or airline credit for the significant delay.

Flight was on time with no issues. Price is very competitive. Flight schedule works well for me

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

Better than expected. Staff were friendly and nice on both flights.

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Everything you need to know for your flight to Florida Keys

Cabin class types available on flights to Chicago

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.