Cheap flights from Chicago (CHI) to Florida Keys

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How to find the cheapest flight from
Chicago (CHI) to Florida Keys

All the information you need to plan the best CHI to MIA flight in 2022: compare Chicago to Florida Keys flight prices with the expected peak season, weather and rainfall in Florida Keys.
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.

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 61 days in advance, which can save you up to 36% on flights from Chicago to Florida Keys compared to booking the week you need them. Waiting 61 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 $496. For sooner than that we have options available in the next 3 days from $626.

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 $430 per person but you can even find prices for as low as $295. The most expensive prices can be found in the month of March. Opting for a September flight can save you 24% on your journey compared to booking in March

Cheap flights from Chicago to Florida Keys in June, July 2022

The best prices found for CHI to Florida Keys flights for June, July
9 Jul - 12 Jul
$63pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
26 Jul - 17 Aug
$90pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
9 Jul - 12 Jul
$94pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Chicago to Florida Keys 2022 flight deals

Cheap flights to Florida Keys from Chicago found for this year
16 Aug - 17 Aug
$56pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
16 Aug - 17 Aug
$61pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
9 Jul - 12 Jul
$63pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Florida Keys from Chicago

Save time with Chicago to Florida Keys direct flight deals
16 Aug - 17 Aug
$56pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
16 Aug - 17 Aug
$61pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
9 Jul - 12 Jul
$63pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Florida Keys

Late deals on round-trip flights to Florida Keys from Chicago, departing today and this week
4 Jul - 12 Jul
$114pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
3 Jul - 7 Jul
$122pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
2 Jul - 9 Jul
$125pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
MIA
Miami
MIA
Miami
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Florida Keys from Chicago

The cheapest one-way flights from Chicago to Florida Keys
3:41 pm - 7:57 pm
Spirit Airlines
Nonstop
3h 16m
ORD - MIA
Spirit Airlines
3:41 pm - 7:57 pm
Spirit Airlines
Nonstop
3h 16m
ORD - MIA
Spirit Airlines
$31
Gotogate
3:41 pm - 7:57 pm
Spirit Airlines
Nonstop
3h 16m
ORD - MIA
Spirit Airlines
$32
Gotogate

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Florida Keys</span> flights.

Flight FAQs

From Chicago to Florida Keys

Which airlines flying from Chicago to Florida Keys have flexible cancellations due to COVID-19?

Spirit Airlines, American Airlines, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Florida Keys for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Florida Keys for under $100. The cheapest flight booked recently is on Spirit Airlines for just $56, but on average you can expect to pay $89.

Are there nonstop flights from Chicago to Florida Keys for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Florida Keys under $100. A good price for a nonstop flight from Chicago to Florida Keys is less than $99.

Are there last-minute flights available from Chicago to Florida Keys for under $200?

There are currently 20+ open flights from Chicago to Florida Keys within the next 7 days for less than $200.

What days are nonstop flights available from Chicago to Florida Keys?

Days when nonstop flights are available for this flight are: Sunday.

How many flights depart from Chicago to Florida Keys on average per day?

2 flight departures from Chicago to Florida Keys per day on average.
Afternoon (Noon - 6pm) - 100% of flight departures

How long is the flight from Chicago to Florida Keys?

For as low as $56, Spirit Airlines can have you in Florida Keys from Chicago in 3h 16m. The distance between Chicago and Florida Keys is about 1205 mi. Most flights are nonstop.

What are the cheapest flights from Chicago to Florida Keys?

Looking at all options, your cheapest flight can be booked for $24. While the most popular route (Chicago O'Hare Intl - Miami) can be booked for $64 on average our data indicates $737 when flying from Chicago to Florida Keys.

What are the most popular airlines that fly from Chicago to Florida Keys?

When booking a flight from Chicago to Florida Keys, you may want to consider flying on Major Airline, American Airlines or Alaska Airlines as they are the most popular for this route.

What are the most reliable airlines from Chicago to Florida Keys?

The top 3 most reliable airlines when flying from Chicago to Florida Keys are Avianca (84%), Air Canada (81%) and Copa Airlines (81%).

What are the most popular routes from Chicago to Florida Keys?

While some choose either Chicago Midway - Miami or Chicago O'Hare Intl - Key West, Chicago O'Hare Intl - Miami is the most popular route from Chicago to Florida Keys.

COVID Restrictions

View COVID Travel Restrictions for Florida Keys

Do I need a COVID test to fly to Florida Keys from Chicago?

Information is based on travel restrictions for travel to Florida Keys within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Florida Keys.

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Florida Keys.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Florida Keys.

Do I need a test to fly back to Chicago from Florida Keys?

Returning to Chicago from Florida Keys

COVID-19 testing requirements
Visitors from Florida Keys are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Florida Keys are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Florida Keys

Alternative routes for Chicago to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.

Destination points for flights from Chicago to Florida Keys

Select to see more specific information for flights from Chicago to all places in Florida Keys.

Destination information for Florida Keys

Things to know before you go - useful duration and weather info for your trip from Chicago to Florida Keys.
Flight duration from Chicago to Florida Keys
3h 20m

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing

Key West (EYW)
Miami Opa Locka (OPF)

Top 8 airlines flying from Chicago to Florida Keys

The chart below displays the airlines Cheapflights users traveling from Chicago to Florida Keys choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
$9 $23 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Frontier
$37 $102 No cancel fee 62%
Spirit Airlines
$48 $190 No cancel fee 65%
JetBlue
$57 $146 No cancel fee 62%
United Airlines
$72 $333 No cancel fee 69%
American Airlines
$79 $366 No cancel fee 71%
Alaska Airlines
$154 $388 No cancel fee 75%
Delta
$183 $470 No cancel fee N/A
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