Cheap flights from Chicago (CHI) to Florida Keys from $29
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/25. 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.
How far in advance should I book a flight from Chicago to Florida Keys?
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 27 days in advance, which can save you up to 66% on flights from Chicago to Florida Keys compared to booking the week you need them. Waiting 27 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $167. For sooner than that we have options available in the next 3 days from $330.
What is the cheapest month to fly from Chicago to Florida Keys?
September is one of the best times of the year to fly to Florida Keys from Chicago. Prices for September average $222 per person but you can even find prices for as low as $52. The most expensive prices can be found in the month of March. Opting for a September flight can save you 40% on your journey compared to booking in March
When is the cheapest time to fly from Chicago to Florida Keys (CHI - EOA)?
When flying from Chicago to Florida Keys, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Cheap Spirit Airlines flights from Chicago to Florida Keys
Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Florida Keys. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Consider these cheap Spirit Airlines flights we've found departing from Chicago to Florida Keys. Be sure to come back soon if the deals available don't appeal to you at this time.
Cheap Frontier flights from Chicago to Florida Keys
Explore cheap flight options specifically provided by Frontier for the route between Chicago and Florida Keys. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Some of the best deals we've found on Frontier flights traveling from Chicago to Florida Keys. Deals are refreshing constantly so come back soon for more options.
Cheap Chicago to Florida Keys flights in May & June 2024
Find cheap flight options from Chicago to Florida Keys specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,864,334 searches. Prices were last updated on May 4, 2024.
Scroll through some of the best deals on flights from Chicago to Florida Keys in 2024. Check back regularly for other flight deals.
Chicago to Florida Keys 2024 flight deals
Discover exclusive flight deals for travel between Chicago and Florida Keys in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Scroll through some of the best deals on flights from Chicago to Florida Keys in 2024. Check back regularly for other flight deals.
Non-stop flights to Florida Keys from Chicago
Discover non-stop flight options from Chicago to Florida Keys. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
For a shorter flight, select one of these non-stop flights from Chicago to Florida Keys. If you're looking for other options for flights from Chicago to Florida Keys, make sure to update the search form at the top of page.
Chicago to Florida Keys flights leaving soon
Find last-minute flight options from Chicago to Florida Keys for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Have a look at some of the last-minute flights available departing from Chicago to Florida Keys. To prevent any unwanted surprises, users should verify their flight info before booking.
One-way flights to Florida Keys from Chicago
Search for one-way flight options from Chicago to Florida Keys. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Take a look at some of the best available options we've come across on one-way flights from Chicago to Florida Keys. Users can also find round-trip Chicago to Florida Keys flights by using the search form above.
Find flights from Chicago to Florida Keys within your budget
Customize your flight search to find flights from Chicago to Florida Keys that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Fly from
Fly to
Budget
$51 - $81
Route
Depart
Return
Price
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 5/14
Nonstop3h 17m
Miami
Sat 5/25
Nonstop3h 27m
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Sat 5/18
Nonstop3h 17m
Miami
Tue 5/21
1 stop11h 57m
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 5/14
Nonstop3h 17m
Miami
Tue 5/21
1 stop11h 57m
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Wed 5/15
Nonstop3h 17m
Miami
Tue 5/21
1 stop11h 57m
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Mon 6/3
Nonstop3h 17m
Miami
Wed 6/5
Nonstop3h 26m
Chicago MidwayMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 6/10
Nonstop3h 07m
Miami
Wed 6/19
Nonstop3h 11m
Chicago MidwayMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 6/3
Nonstop3h 11m
Miami
Wed 6/12
Nonstop3h 11m
Chicago MidwayMiami
MDW - MIA
MDWMIA
Chicago Midway
Mon 6/3
Nonstop3h 11m
Miami
Thu 6/6
Nonstop3h 16m
Chicago O'Hare IntlMiami
ORD - MIA
ORDMIA
Chicago O'Hare Intl
Tue 5/14
Nonstop3h 17m
Miami
Sat 5/25
1 stop17h 38m
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Florida Keys
Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated May 4, 2024.
Read through reviews of airlines operating flights from Chicago to Florida Keys, such as Spirit Airlines, Frontier and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Comfort
Crew
Boarding
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Comfort
Crew
Boarding
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Comfort
Crew
Boarding
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Comfort
Crew
Boarding
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Comfort
Crew
Boarding
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Comfort
Crew
Boarding
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Florida KeysSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Chicago to Florida Keys
Discover the top 4 airlines that operate flights from Chicago to Florida Keys. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,864,334 searches. Data last updated May 4, 2024.
Search flights from Chicago to Florida Keys by cabin class
Find flights from Chicago to Florida Keys, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Chicago to Florida Keys
Find hourly flight availability from Chicago to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 4, 2024.
| 0%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 100%of flight departures | Morning6 am to noon |
| 0%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
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How does Cheapflights help users find flights from Chicago to Florida Keys?
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Why should you use Cheapflights to find cheap flight tickets from Chicago to Florida Keys?
Cheapflights helps you find that perfect flight to Florida Keys from Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from Chicago to Florida Keys with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago to Florida Keys flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Chicago to Florida Keys become cheaper?
Yes, Cheapflights offers price alerts on Chicago to Florida Keys flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.