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$58 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Search hundreds of travel sites at once for deals on flights 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida Keys, as well as popular online travel agencies
In the last 7 days travelers have searched 46,479,581 times on KAYAK, and here is why:

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Best Florida Keys Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Miami
Miaminonstop$88
Key West
Key Westnonstop$249

Good to know

Low season

September

High season

March

Cheapest flight

$58
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 27% 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 to Florida Keys from Chicago O'Hare Airport 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 to Florida Keys with an airline and back to Chicago O'Hare Airport 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 to Florida Keys from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $138 one-way - $295 round-trip

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.
8.0
DeltaOverall score based on 8835 reviews
8.5Crew
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

4.0 OkayDale, Sep 2024BOS - TPA
Read more Delta reviews

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Didn't make it dir to delays - no support from United staff

My flight was delayed for a whole day, so I lost a day of my vacation.

flight delayed, was put on another flight after standby queue, luggage was misplaced and arrived to me 3 days later

The baggage handlers broke the handle on my bag that they put under the plane that I checked on the jetway. They traded it out for a less quality bag in Tulsa. But, they said they would try to fix it. Bologna! There was no fixing that bag handle. Someone didn’t care how they treated the bag.

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

BAD. As a family could not sit together. The gate agent told us there was only one seat in the middle left, when we got on the plane the situation was very different with whole rows of seats empty

Everything was excellent and as expected. The boarding process was great but deboarding was a bit slow. No fault of the crew; it just seemed like the passengers didn’t want to leave! 😂

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

The flight was delayed and the announcements were hard to hear, but the crew was great

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

Really nice, flight attendants were so helpful with me and my kids. Extremely grateful, keep up the good work and spirit :)

I liked the low price. I did not like the cramped passenger seats. As a below average size person I was cramped in the seat; I can only imagine how uncomfortable an average or large size person would be. I guess that is part of the deal with low cost airlines.

It just baffled me that spirit boarding process that I was charged 2 check in fees for a person bag and carry on. I ended up lugging 3 kids under 10 with 2 bags and to find out at the boarding area that I could not get on the plane due to my lack of reading the baggage policy. I understand if that was the case but the agent also failed to understand one item was in fact a personal item such as laptop bag and charge me as if it was a carry on not personal item. And knowing it’s a horrible storm and last flight in the destination of travel. I could have very easily handed the items to my relative to keep but I didn’t learned about this enforced policy until I was about to board.

I’m not a fan of Spirit Airlines from a not-so-good experience the last time & I swore I would not fly this airline again- bc they charge for EVERYTHING. I only flew Spirit this time bc it wasn’t my choice. I decided to use a “Mystery Ticket” bc of the great price, not knowing it would choose this airline! I found out on this trip how they pick a random seat with a “sticker” for a prize-are we in first grade? just doesn’t seem right & now the first 3 or 4 rows get special treatment-we all paid for our tickets, not just them.

The flight was delayed, and we waited for more than an hour on the plane.

This was the best spirit airlines fight I have ever had. I take spirit up to 3 or more times a year and I am ready to be the Jared of spirit. 🤪 Best flight ever. Everyone was great. I hope my return flight is the same. When you're traveling with a 9 month old you need a different type of care and accommodation. I didn't ask the staff for anything but I didn't have any added stress.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Airline changed the gate from Terminal A to Terminal D which is quite far and only sent a text message few minutes before boarding. Around 50 people missed their flight and as plane didn’t wait for them.

The personal at boarding are rude and try to steel people with their rule of personal item , really bad experience for us

I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

Horrible my trip was delayed 3 hours, we already have set in the plane and they delayed the flight.

Checking in was easy and simple, crew was nice and efficient, but I would improve seat assignment randomness to make it easier to sit together based on when you check in. Overall would fly with them again.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

Book cheap flights from Chicago to Florida Keys

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Chicago to Florida Keys found on KAYAK in the last 72 hours.
12/3Tue
nonstopSpirit Airlines
3h 18mORD-MIA
12/4Wed
nonstopSpirit Airlines
3h 29mMIA-ORD
$88
1/25Sat
nonstopSpirit Airlines
3h 14mORD-MIA
1/28Tue
nonstopSpirit Airlines
3h 31mMIA-ORD
$96
11/16Sat
1 stopFrontier
11h 08mORD-MIA
11/18Mon
1 stopFrontier
26h 26mMIA-ORD
$106
11/15Fri
1 stopFrontier
18h 17mORD-MIA
11/18Mon
1 stopFrontier
15h 57mMIA-ORD
$116
12/3Tue
nonstopAmerican Airlines
3h 23mORD-MIA
12/7Sat
nonstopAmerican Airlines
3h 34mMIA-ORD
$159
11/13Wed
nonstopUnited Airlines
3h 16mORD-MIA
11/20Wed
nonstopUnited Airlines
3h 27mMIA-ORD
$184
2/7Fri
nonstopAmerican Airlines
3h 13mORD-MIA
2/13Thu
nonstopAmerican Airlines
3h 31mMIA-ORD
$197
1/25Sat
1 stopDelta
5h 54mORD-MIA
1/30Thu
1 stopDelta
6h 09mMIA-ORD
$217
11/16Sat
nonstopUnited Airlines
3h 16mORD-MIA
11/23Sat
nonstopUnited Airlines
3h 28mMIA-ORD
$236
12/14Sat
1 stopDelta
4h 57mORD-EYW
12/18Wed
1 stopDelta
7h 16mEYW-ORD
$268

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Florida Keys found on KAYAK in the last 72 hours.
12/18Wed
nonstopSpirit Airlines
3h 18mORD-MIA
$58
12/5Thu
1 stopFrontier
17h 27mORD-MIA
$59
11/20Wed
nonstopAmerican Airlines
3h 07mORD-MIA
$80
11/16Sat
nonstopUnited Airlines
3h 16mORD-MIA
$105
11/20Wed
nonstopUnited Airlines
3h 16mORD-MIA
$120
11/11Mon
1 stopSouthwest
10h 00mORD-MIA
$163
12/21Sat
1 stopAmerican Airlines
5h 35mORD-MIA
$176
1/19Sun
2 stopsSouthwest
10h 05mORD-MIA
$181
11/27Wed
1 stopDelta
7h 30mORD-EYW
$263
12/29Sun
1 stopDelta
5h 27mORD-EYW
$319

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Last minute flights from O'Hare Intl to Florida Keys

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Florida Keys that are departing in the next 10 days.
11/4Mon
nonstop
3h 13mORD-MIA
11/14Thu
multi-stop
5h 35mMIA-ORD
$175
11/3Sun
multi-stop
11h 24mORD-MIA
11/7Thu
multi-stop
5h 35mMIA-ORD
$176
11/4Mon
nonstopSpirit Airlines
3h 13mORD-MIA
11/13Wed
multi-stopSpirit Airlines
7h 56mMIA-ORD
$178
11/5Tue
multi-stopSpirit Airlines
7h 37mORD-MIA
11/16Sat
multi-stopSpirit Airlines
8h 48mMIA-ORD
$190
11/2Sat
multi-stopFrontier
18h 59mORD-MIA
11/7Thu
multi-stopFrontier
5h 35mMIA-ORD
$252
11/2Sat
multi-stopFrontier
18h 59mORD-MIA
11/11Mon
multi-stopFrontier
26h 26mMIA-ORD
$262
11/5Tue
nonstopUnited Airlines
3h 16mORD-MIA
11/6Wed
nonstopUnited Airlines
3h 28mMIA-ORD
$377
11/5Tue
nonstopUnited Airlines
3h 16mORD-MIA
11/6Wed
multi-stopUnited Airlines
8h 43mMIA-ORD
$382
11/2Sat
multi-stopAmerican Airlines
5h 45mORD-EYW
11/5Tue
nonstopAmerican Airlines
3h 31mEYW-ORD
$509
11/2Sat
multi-stopAmerican Airlines
8h 01mORD-EYW
11/5Tue
multi-stopAmerican Airlines
8h 08mEYW-ORD
$523

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Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports