$101 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 7/14. 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
Miami1 stop$193
Key West
Key West1 stop$319
Miami
Miami1 stop$193
Key West
Key West1 stop$319

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

Wed, Sep 16 - Tue, Sep 22
United Airlines Logo
5:55 am - 2:46 pm
ORD
-
MIA
7h 51m
1 stop
United Airlines Logo
12:17 pm - 2:48 pm
MIA
-
ORD
3h 31mnonstop
$193United Airlines
Tue, Aug 4 - Sat, Aug 8
United Airlines Logo
10:33 am - 2:57 pm
ORD
-
MIA
3h 24mnonstop
United Airlines Logo
6:30 am - 12:29 pm
MIA
-
ORD
6h 59m
1 stop
$197United Airlines
Mon, Aug 10 - Wed, Aug 12
Southwest Logo
5:30 am - 3:20 pm
MDW
-
MIA
8h 50m
1 stop
Southwest Logo
4:00 pm - 6:05 pm
MIA
-
MDW
3h 05mnonstop
$197Southwest
Tue, Aug 4 - Tue, Aug 11
Frontier Logo
7:05 am - 1:53 pm
ORD
-
MIA
5h 48m
1 stop
Frontier Logo
6:50 am - 8:15 pm
MIA
-
ORD
14h 25m
1 stop
$201Frontier
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
6:00 am - 10:07 am
ORD
-
MIA
3h 07mnonstop
American Airlines Logo
10:05 pm - 12:35 am
MIA
-
ORD
3h 30mnonstop
$203American Airlines
Sat, Aug 8 - Mon, Aug 10
American Airlines Logo
5:59 pm - 10:17 pm
ORD
-
MIA
3h 18mnonstop
American Airlines Logo
8:59 pm - 11:30 pm
MIA
-
ORD
3h 31mnonstop
$204American Airlines
Mon, Aug 10 - Wed, Aug 12
Southwest Logo
5:30 am - 2:40 pm
MDW
-
MIA
8h 10m
1 stop
Southwest Logo
6:05 pm - 10:20 pm
MIA
-
MDW
5h 15m
1 stop
$207Southwest
Tue, Aug 4 - Tue, Aug 11
Frontier Logo
1:50 pm - 11:05 pm
ORD
-
MIA
8h 15m
1 stop
Frontier Logo
6:50 am - 4:00 pm
MIA
-
ORD
10h 10m
1 stop
$210Frontier
Tue, Jul 14 - Tue, Jul 21
Delta Logo
6:00 am - 1:02 pm
MDW
-
MIA
6h 02m
1 stop
Delta Logo
6:00 pm - 10:15 pm
MIA
-
MDW
5h 15m
1 stop
$217Delta
Wed, Jul 29 - Wed, Aug 5
Delta Logo
11:05 am - 7:51 pm
MDW
-
EYW
7h 46m
1 stop
Delta Logo
6:15 pm - 10:36 pm
EYW
-
MDW
5h 21m
1 stop
$329Delta
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 5 days was to Key West, at $309 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 5 days was $309.

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 $379 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $464.

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 $465, 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 October, when tickets cost $221 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $403 and $364 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 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$101
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 16% 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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Very easy to use and convenient, you can perform any action within the same portal

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Okay considering we had weather delays which the Pilot notified us of immediately!

N Everything was perfect from boarding to assistance to baggage in Tampa

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

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.

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.