$53 Find Cheap Flights from Chicago to Islamorada

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 Islamorada departing on 3/31. 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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Everything you should know

Cheapest round-trip
$99
Overall average: $237
Multiple Airlines
Thu 1/22Thu 1/29
ORD - MIA • 1 stop
Cheapest non-stop
$99
Typical prices: $133-$413
Frontier
Mon 1/5Mon 1/12
MDW - MIA • Non-stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Islamorada (CHI-MIA)

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

Thu, Jan 22 - Thu, Jan 29
Multiple Airlines Logo
5:40 am - 11:56 am
ORD
-
MIA
5h 16m1 stop
Multiple Airlines Logo
5:54 am - 8:18 am
MIA
-
ORD
3h 24mnonstop
$99Multiple Airlines
Mon, Jan 5 - Mon, Jan 12
Frontier Logo
6:15 am - 10:32 am
MDW
-
MIA
3h 17mnonstop
Frontier Logo
11:43 am - 2:06 pm
MIA
-
MDW
3h 23mnonstop
$99Frontier
Wed, Jan 28 - Wed, Feb 4
Multiple Airlines Logo
9:23 am - 1:41 pm
ORD
-
MIA
3h 18mnonstop
Multiple Airlines Logo
1:21 pm - 6:27 pm
MIA
-
ORD
6h 06m1 stop
$100Multiple Airlines
Mon, Jan 12 - Tue, Jan 20
Spirit Airlines Logo
6:57 pm - 11:14 pm
ORD
-
MIA
3h 17mnonstop
Spirit Airlines Logo
7:00 am - 11:46 pm
MIA
-
ORD
17h 46m2 stops
$101Spirit Airlines
Tue, Jan 6 - Tue, Jan 13
Spirit Airlines Logo
6:05 pm - 10:21 pm
ORD
-
MIA
3h 16mnonstop
Spirit Airlines Logo
1:01 pm - 10:38 pm
MIA
-
ORD
10h 37m1 stop
$102Spirit Airlines
Fri, Feb 6 - Mon, Feb 16
Multiple Airlines Logo
6:57 pm - 11:14 pm
ORD
-
MIA
3h 17mnonstop
Multiple Airlines Logo
8:00 am - 10:38 am
MIA
-
ORD
3h 38mnonstop
$103Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
5:58 pm - 1:14 am
ORD
-
MIA
6h 16m1 stop
Multiple Airlines Logo
7:12 am - 9:39 am
MIA
-
ORD
3h 27mnonstop
$104Multiple Airlines
Mon, Jan 5 - Wed, Jan 7
Spirit Airlines Logo
6:05 pm - 10:21 pm
ORD
-
MIA
3h 16mnonstop
Spirit Airlines Logo
2:35 pm - 5:00 pm
MIA
-
ORD
3h 25mnonstop
$105Spirit Airlines
Mon, Jan 5 - Fri, Jan 23
Spirit Airlines Logo
6:05 pm - 10:21 pm
ORD
-
MIA
3h 16mnonstop
Spirit Airlines Logo
3:48 pm - 6:16 pm
MIA
-
ORD
3h 28mnonstop
$106Spirit Airlines
Thu, Feb 19 - Wed, Feb 25
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
12:10 pm - 7:07 pm
MIA
-
MDW
7h 57m1 stop
$109Frontier
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$53
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago O'Hare Airport to Miami

When to book flights from Chicago to Islamorada

Are your dates flexible? Find out the best times to travel from Chicago to Islamorada based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Islamorada

  • Which airports will I be using when flying from Chicago to Islamorada?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Islamorada does not have its own airport so you’ll be flying into nearby Miami airport, which is 63.9 mi away.

  • How long does a flight from Chicago to Islamorada take?

    Direct flights cover the 1,186 miles separating Chicago and Islamorada in about 3h 00m.

  • How many flights are there between Chicago and Islamorada?

    68 direct flights run between Chicago and Islamorada on a daily basis. On average, there are about 478 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Islamorada?

    Consider leaving on a Tuesday and avoid Fridays 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 Thursdays.

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

    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 Islamorada.

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

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

    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 Islamorada with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Islamorada?

    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 Islamorada from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Islamorada?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Islamorada found on KAYAK was with Frontier for $39. Frontier offered a round-trip connection from $39 and Spirit Airlines from $79.

Top tips for finding cheap flights from Chicago to Islamorada

  • There is no airport in Islamorada. Instead, you’ll be flying into Miami Airport when flying between Chicago and Islamorada.
  • The cheapest flight from Chicago to Islamorada was found 69 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is September.

Reviews of the top 5 airlines serving Chicago to Islamorada

 
Need help choosing which airline to fly with from Chicago to Islamorada? 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 4257 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

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.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

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.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

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.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

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.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

The most horrible flight ever not only Spirit delayed our flight 2 hours departure time for a 1 hour flight — that I could have driven FLL to TPA and spend less time on the road —- and they did the same on the return with 2-hr delay again!!! Then to top all, the rubber like and most unconfortable seats in the industry with no leg room!!! There should be an award for these kinds of companies measuring % of returning customers!!!

Horrible. Arrived at my gate at 6:37 for a 6:50 flight and was denied by staff to board. Literally watched my flight leave from the window and it didn’t take off until after 7am. Tried to talk to staff and they were rude beyond compare. Will never fly with this airline again.

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Flight was canceled and instead of rescheduling at the gate we had to go out to the ticket counter. Unruly kids kicking the back of my rows chair with staff to inattentive to say something.

I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Terrible Airline I will never fly that airline again. Shame on you for recommending them.

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

I hope you continue to be one of the great company

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

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Everything you need to know for your flight from Chicago to Islamorada

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