Cheap flights from Chicago to Florida Keys from $42
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Florida Keys departing on 7/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines flights from Chicago to Florida Keys
Our best Spirit Airlines deals on Chicago to Florida Keys flight tickets
American Airlines flights from Chicago to Florida Keys
Our best American Airlines deals on Chicago to Florida Keys flight tickets
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How to get the cheapest flight ticket from Chicago to Florida Keys
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Florida Keys?
The month of July is another great option to travel to Florida Keys, with average flight prices from Chicago averaging around $183.
What is the cheapest day to depart on your flight to Florida Keys?
The cheapest day to depart from Chicago to Florida Keys is on a Thursday when prices can be found for as low as $430. The most expensive day to fly to Florida Keys is Monday, with ticket prices averaging around $462.
What is the cheapest time of day to depart on your flight to Florida Keys?
According to our data, the cheapest time of day to fly to Florida Keys is in the evening. momondo users have found flights departing from Chicago to Florida Keys in the evening for as low as $233. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the morning are often more expensive with an average ticket price of $483.
What is the cheapest Chicago to Florida Keys flight route?
Fly from Chicago O'Hare Intl to Key West for the best Chicago - Florida Keys flight prices
How far in advance should I book a flight to Florida Keys?
You are more likely to see cheaper flights to Florida Keys from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $268 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida Keys from Chicago for as low as $213 on momondo.
What cabin class options are available on Chicago to Florida Keys flights?
There are 3 cabin classes available to choose from on Chicago to Florida Keys flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Florida Keys?
Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Chicago to Florida Keys
What airlines fly to Florida Keys?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Florida Keys from Chicago according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Florida Keys. Keep in mind that there are 3 different airlines that fly to Florida Keys on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Florida Keys on average per day?
The number of flights available between Chicago and Florida Keys is 40 per day as of June 2025. The most frequent departure time is 8:00AM, with 100% of daily flights leaving at noon.
How many flights depart from Chicago to Florida Keys on average per week?
As of June 2025, 280 flights take off from Chicago and land in Florida Keys each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.
Cheap Chicago to Florida Keys flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Florida Keys
Best Price Found | $42 |
|---|---|
Fastest flight time | 3h 00m |
Direct flights | Mon, Tue, Fri, Sat and Sun |
Airports in Florida Keys | 1 airport |
When did momondo last update prices for flights from Chicago to Florida Keys?
Prices for flights from Chicago to Florida Keys were last updated today.
How many operators does momondo search for flights from Chicago to Florida Keys?
There are 7 operators available for flights from Chicago to Florida Keys as of June 2025.
How old do you have to be to fly from Chicago to Florida Keys?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Florida Keys.
What documentation or ID do you need to fly to Florida Keys?
The travel and health documents you'll need for your trip to Florida Keys may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Florida Keys. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Florida Keys?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Florida Keys is Boeing 737-800, representing 16.54% of all bookings. The subsequent popular models are Airbus A321neo at 9.86%, Boeing 737-900 at 7.82%, and Airbus A320neo at 6.83%.
Best airlines flying from Chicago to Florida Keys
Compare and see reviews for airlines that fly from Chicago to Florida Keys with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $265 | Free Cancellation | Rating 7.4 8,838 reviews | |||
| PriceFrom $283 | Free Cancellation | Rating 7.2 10,000 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Florida Keys?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Florida Keys. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Florida Keys with flexible booking policies on momondo?
All flight searches from Chicago to Florida Keys on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Florida Keys?
momondo helps you find the best flight between Chicago and Florida Keys by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Florida Keys right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Florida Keys from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.