Find flights
Deals
When to book
FAQs & Tips
Airlines

$28 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 7/17. 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
0 bags
Wed 7/17
Wed 7/24

Search hundreds of travel sites at once for deals on flights to Florida Keys

In the last 7 days travelers have searched 44,229,043 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Best Florida Keys Flight Deals

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

Miami
Miaminonstop$53
Key West
Key West1 stop$248

Good to know

Low season

September

High season

March

Cheapest flight

$28
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 30% 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 $90 one-way - $202 round-trip

Top 5 airlines serving from O'Hare Intl to Florida Keys

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 10000 reviews
8.0Entertainment
8.6Crew
7.4Food
7.9Comfort
8.2Boarding
Airline reviews

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

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

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.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

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.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

I missed this flight due to delays on my previous flight.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Three out of four legs of my trip were delayed. The last leg of my trip was delayed due to passengers and crew not being ready to take off. The boarding process started way late with no explanation as to why. The flight attendants did not have the passengers in check for takeoff - folks were walking around, trying to change seats, and causing a general disturbance preventing us from departing and the crew did nothing about it. All of this caused us to miss my connection home due to the first flight landing at the same time the second one was due to take off. The entire Spirit crew (except for one flight attendant) was unapologetic and unpleasant about this. No one apologized, no one showed any inkling of empathy whatsoever. The response was basically, "we booked you on the next available flight". That next flight was a full 24 hours later, we would have been stranded in the airport and no one even cared or acknowledged us as customers. I'm disappointed in the lack of compassion shown by Spirit agents and customer service reps as a whole. It felt like we were a burden due to airline scheduling issues. The one flight attendant (did not catch her name, but from (ORD to FLL) was wonderful and empathetic.

The bag drop process took longer than other airlines. The boarding and crew were good. The seats do not recline and have minimal padding. The snacks/drinks are for purchase only. The flight was on time with no issues. I would fly them again if the cost was significantly less.

Crew was excellent. Flight was overbooked No seat assignment until the last moment.

Poor response to delay, getting on plane, off plane and back on again

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

The plane was not on time for boarding or departure or arrivals.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

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.

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

Book cheap flights from Chicago to Florida Keys

Recent round-trip flight deals

9/4Wed
nonstopSpirit Airlines
3h 14mORD-MIA
9/11Wed
nonstopSpirit Airlines
3h 21mMIA-ORD
$59
9/4Wed
nonstopSpirit Airlines
3h 14mORD-MIA
9/11Wed
nonstopSpirit Airlines
3h 21mMIA-ORD
$60
9/6Fri
1 stopFrontier
6h 06mORD-MIA
9/14Sat
1 stopFrontier
8h 51mMIA-ORD
$97
8/16Fri
1 stopFrontier
6h 06mORD-MIA
8/21Wed
1 stopFrontier
8h 35mMIA-ORD
$98
7/16Tue
1 stopDelta
6h 46mORD-EYW
7/23Tue
1 stopDelta
6h 51mEYW-ORD
$248
8/23Fri
1 stopDelta
6h 35mORD-EYW
8/27Tue
1 stopDelta
5h 01mEYW-ORD
$268
9/6Fri
1 stopAmerican Airlines
7h 02mORD-EYW
9/9Mon
1 stopAmerican Airlines
6h 40mEYW-ORD
$273
7/17Wed
1 stopUnited Airlines
7h 09mORD-EYW
7/24Wed
1 stopUnited Airlines
9h 07mEYW-ORD
$277
9/6Fri
1 stopAmerican Airlines
5h 27mORD-EYW
9/9Mon
2 stopsAmerican Airlines
6h 55mEYW-ORD
$278
7/10Wed
1 stopUnited Airlines
7h 09mORD-EYW
7/17Wed
1 stopUnited Airlines
9h 07mEYW-ORD
$328

Search by stops

Search by airline

Search by price

Recent one-way flight deals

7/17Wed
nonstopSpirit Airlines
3h 18mORD-MIA
$28
7/16Tue
nonstopSpirit Airlines
3h 15mORD-MIA
$29
7/31Wed
1 stopFrontier
6h 11mORD-MIA
$69
7/8Mon
1 stopFrontier
6h 16mORD-MIA
$70
8/2Fri
nonstopAmerican Airlines
3h 09mORD-MIA
$99
9/1Sun
1 stopAmerican Airlines
6h 21mORD-EYW
$99
8/18Sun
1 stopDelta
7h 43mORD-MIA
$108
7/4Thu
1 stopDelta
6h 38mORD-EYW
$108
7/18Thu
nonstopUnited Airlines
3h 14mORD-MIA
$189
9/2Mon
1 stopUnited Airlines
26h 50mORD-EYW
$253

Search by stops

Search by airline

Search by price

Last minute flights from O'Hare Intl to Florida Keys

Last minute flight, train and bus deals

6/22Sat
nonstopSpirit Airlines
3h 18mORD-MIA
6/30Sun
nonstopSpirit Airlines
3h 29mMIA-ORD
$120
6/22Sat
nonstopSpirit Airlines
3h 18mORD-MIA
6/30Sun
nonstopSpirit Airlines
3h 29mMIA-ORD
$127
6/22Sat
nonstopSpirit Airlines
3h 17mORD-MIA
6/25Tue
nonstopSpirit Airlines
3h 26mMIA-ORD
$149
6/22Sat
nonstopSpirit Airlines
3h 18mORD-MIA
6/29Sat
nonstopSpirit Airlines
3h 33mMIA-ORD
$152
6/21Fri
multi-stop
7h 54mORD-MIA
6/25Tue
multi-stop
6h 06mMIA-ORD
$175
6/18Tue
multi-stop
7h 56mORD-MIA
6/25Tue
multi-stop
6h 06mMIA-ORD
$210
6/20Thu
multi-stopFrontier
14h 29mORD-MIA
6/27Thu
multi-stopFrontier
18h 10mMIA-ORD
$215
6/18Tue
multi-stopFrontier
15h 16mORD-MIA
6/23Sun
multi-stopFrontier
18h 10mMIA-ORD
$349
6/19Wed
multi-stopAmerican Airlines
7h 36mORD-EYW
6/22Sat
multi-stopAmerican Airlines
5h 58mEYW-ORD
$488
6/19Wed
multi-stopAmerican Airlines
8h 00mORD-EYW
6/22Sat
multi-stopAmerican Airlines
5h 58mEYW-ORD
$493

Search by stops

Search by airline

Search by price

Chicago O'Hare Airport - Florida Keys Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Florida Keys - Chicago O'Hare Airport

Cabin classes:

$172
$194
$265
$38