$63 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 9/29. 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

KAYAK searches 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.
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$106
Key West
Key West1 stop$221
Miami
Miami1 stop$106
Key West
Key West1 stop$221

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, Sep 30 - Sat, Oct 4
Spirit Airlines Logo
11:13 am - 11:17 pmORD-MIA
11h 04m1 stop
Spirit Airlines Logo
7:00 am - 9:18 amMIA-ORD
3h 18mnonstop
$106Spirit Airlines
Find Deal
Thu, Oct 9 - Sun, Oct 12
Spirit Airlines Logo
10:27 am - 2:29 pmORD-MIA
3h 02mnonstop
Spirit Airlines Logo
7:00 am - 9:22 amMIA-ORD
3h 22mnonstop
$107Spirit Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
7:05 am - 11:09 amORD-MIA
3h 04mnonstop
American Airlines Logo
6:59 pm - 9:23 pmMIA-ORD
3h 24mnonstop
$133American Airlines
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Fri, Nov 7 - Mon, Nov 10
Frontier Logo
11:53 am - 12:54 amORD-MIA
12h 01m1 stop
Frontier Logo
7:07 pm - 12:11 amMIA-ORD
6h 04m1 stop
$141Frontier
Find Deal
Fri, Oct 10 - Mon, Oct 13
Frontier Logo
5:50 am - 9:13 pmORD-MIA
14h 23m1 stop
Frontier Logo
8:00 am - 12:44 amMIA-ORD
17h 44m1 stop
$142Frontier
Find Deal
Wed, Oct 29 - Sun, Nov 2
United Airlines Logo
10:35 am - 2:50 pmORD-MIA
3h 15mnonstop
United Airlines Logo
7:00 am - 9:29 amMIA-ORD
3h 29mnonstop
$157United Airlines
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Tue, Feb 24 - Thu, Mar 5
Delta Logo
11:19 am - 7:44 pmORD-EYW
7h 25m1 stop
Delta Logo
1:30 pm - 7:25 pmEYW-ORD
6h 55m1 stop
$269Delta
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Tue, Mar 3 - Tue, Mar 10
United Airlines Logo
10:44 am - 3:00 pmORD-EYW
3h 16mnonstop
United Airlines Logo
4:53 pm - 10:36 pmEYW-ORD
6h 43m1 stop
$276United Airlines
Find Deal
Tue, Feb 24 - Wed, Mar 4
American Airlines Logo
10:59 am - 3:29 pmORD-EYW
3h 30mnonstop
American Airlines Logo
4:00 pm - 6:36 pmEYW-ORD
3h 36mnonstop
$303American Airlines
Find Deal
Wed, Oct 22 - Sat, Nov 1
Delta Logo
9:42 am - 5:12 pmORD-EYW
6h 30m1 stop
Delta Logo
7:40 am - 12:16 pmEYW-ORD
5h 36m1 stop
$320Delta
Find Deal
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 $329 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 $329.

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 $401, 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 $214 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $365 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 Friday and more expensive on a Sunday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Friday, and avoid Sundays 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 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$63
Best time to beat the crowds with an average 10% 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 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 $262 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 $465.

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 $109 one-way - $238 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.
8.0
SouthwestOverall score based on 4242 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

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.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

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

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Everything you need to know for your flight to Florida Keys

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