$42 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Florida Keys departing on 3/4. 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 O'Hare Intl to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$86
Key West
Key West1 stop$289
Miami
Miami1 stop$86
Key West
Key West1 stop$289

Book Cheap O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to Florida Keys

Tue, Mar 3 - Thu, Mar 5
Spirit Airlines Logo
9:18 am - 8:51 pm
ORD
-
MIA
10h 33m
1 stop
Spirit Airlines Logo
7:12 am - 9:39 am
MIA
-
ORD
3h 27mnonstop
$86Spirit Airlines
Wed, Feb 18 - Fri, Feb 20
Spirit Airlines Logo
9:18 am - 1:36 pm
ORD
-
MIA
3h 18mnonstop
Spirit Airlines Logo
7:12 am - 9:39 am
MIA
-
ORD
3h 27mnonstop
$87Spirit Airlines
Sun, Feb 22 - Tue, Feb 24
Spirit Airlines Logo
7:23 pm - 11:39 pm
ORD
-
MIA
3h 16mnonstop
Spirit Airlines Logo
7:12 am - 9:39 am
MIA
-
ORD
3h 27mnonstop
$88Spirit Airlines
Sat, Feb 21 - Tue, Feb 24
Multiple Airlines Logo
11:48 am - 4:03 pm
ORD
-
MIA
3h 15mnonstop
Multiple Airlines Logo
7:12 am - 9:39 am
MIA
-
ORD
3h 27mnonstop
$89Multiple Airlines
Mon, Mar 2 - Fri, Mar 6
Multiple Airlines Logo
8:59 am - 8:51 pm
ORD
-
MIA
10h 52m
1 stop
Multiple Airlines Logo
1:00 pm - 3:38 pm
MIA
-
ORD
3h 38mnonstop
$90Multiple Airlines
Thu, Feb 26 - Tue, Mar 3
Spirit Airlines Logo
7:23 pm - 11:39 pm
ORD
-
MIA
3h 16mnonstop
Spirit Airlines Logo
7:12 am - 9:39 am
MIA
-
ORD
3h 27mnonstop
$91Spirit Airlines
Tue, Feb 10 - Sat, Mar 7
Multiple Airlines Logo
9:23 am - 1:41 pm
ORD
-
MIA
3h 18mnonstop
Multiple Airlines Logo
7:15 am - 9:53 am
MIA
-
ORD
3h 38mnonstop
$92Multiple Airlines
Fri, Apr 3 - Wed, Apr 8
American Airlines Logo
1:39 pm - 10:37 pm
ORD
-
EYW
7h 58m
1 stop
American Airlines Logo
1:07 pm - 3:54 pm
EYW
-
ORD
3h 47mnonstop
$289American Airlines
Wed, Mar 4 - Mon, Mar 9
Delta Logo
11:18 am - 7:42 pm
ORD
-
EYW
7h 24m
1 stop
Delta Logo
6:25 pm - 11:54 pm
EYW
-
ORD
6h 29m
1 stop
$294Delta
Sat, Feb 21 - Fri, Mar 6
United Airlines Logo
5:45 am - 3:53 pm
ORD
-
EYW
9h 08m
1 stop
United Airlines Logo
4:55 pm - 11:59 pm
EYW
-
ORD
8h 04m
1 stop
$299United Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Florida Keys flights

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

What is the cheapest Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport 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 $425, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Florida Keys is September, when tickets cost $193 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $351 and $346 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Florida Keys?

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

Your flight ticket price will generally be cheaper if you fly to Florida Keys on a Monday and more expensive on a Tuesday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Friday, and avoid Mondays for better deals.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Florida Keys, you should book around 2 weeks before departure, which saves you about 31% 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$42
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 28% 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 O'Hare Airport 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 O'Hare Airport to Florida Keys.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $318 on average. Morning departures are around 4% 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 $412.

Top tips for finding cheap flights to Florida Keys

  • Looking for a cheap flight? 25% of our users found tickets from Chicago O'Hare Airport to the following destinations at these prices or less: Miami $113 one-way - $222 round-trip

Reviews of the top 5 airlines serving from O'Hare Intl 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 O'Hare Intl 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
DeltaOverall score based on 8130 reviews
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
7.9Comfort
Airline reviews

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

2.0 MediocreAnonymous, Jan 2026
ATL - FLL
Read more Delta reviews

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

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. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Everything was OK, the deicing took a long time, our connections were almost missed.

Flight was cancelled. But kayak thought it was still on time.

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

This was my best experience with spirit. I flew you guys 4 times and I must say this was the BEST

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Flight was delayed would have liked it to have been on time. I didn't experience the food or entertainment but the boarding process was smooth and the flight crew worked well together and did a great job!

Cheap, only one short delay. No issues despite bad weather. Able to take a big backpack for free.

I know Spirit gets a lot of criticism, but I've taken three flights recently and all were very good, and tremendous value. On my most recent one, they randomly assigned me to a very comfortable exit row seat! The flight was on time and the boarding process was smooth, and the crew was friendly. No complaints!

My experience with spirit was horrible I had to spend a extra $100 to check in my bag when I already purchased my ticket even when I got to my gate to get my seat the attendant didnt say anything until I was boarding the plane..also to make matters worst I been flying from Florida to New york and Florida to Atlanta often this was my 4th trip to Atlanta with the same bag and never had this problem till yesterday so im extremely upset and I wasnt even giving a reason for the change the attendant just gave a attitude and wouldn't answer me at all

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.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports