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 O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Florida Keys. Keep in mind that there are 4 different airlines that fly to Florida Keys on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago O'Hare Intl to Florida Keys?

United Airlines, Spirit Airlines, and Delta are the most popular carriers operating from Chicago O'Hare Intl to Florida Keys

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Florida Keys?

As of February 2026, there are 6 operators available to choose from for flights from Chicago O'Hare Intl Airport to Florida Keys.

How old do you have to be to fly from Chicago O'Hare Intl Airport to Florida Keys?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Florida Keys.

What documentation or ID do you need to fly to Florida Keys?

The required travel and health documents for your Florida Keys trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Florida Keys. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$43 Cheap Flights from Chicago O'Hare Intl Airport to Florida Keys in 2026

Q: How many flights depart from Chicago O'Hare Intl Airport to Florida Keys on average per week?

As of February 2026, 318 flights take off from Chicago O'Hare Intl Airport and land in Florida Keys each week. The most common flight departure day for this route is Fri, with 19% of weekly flights taking off on this day.

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Find the cheapest flights from Chicago O'Hare Intl Airport to Florida Keys

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:23 pm - 11:39 pm

ORD

MIA

3h 16mnonstop

7:15 am - 9:53 am

MIA

ORD

3h 38mnonstop

$81Multiple Airlines

Tue, Mar 3 - Sat, Mar 7

9:05 pm - 1:20 am

ORD

MIA

3h 15mnonstop

7:12 am - 9:39 am

MIA

ORD

3h 27mnonstop

$82Multiple Airlines

Mon, Mar 9 - Wed, Mar 11

10:48 am - 3:03 pm

ORD

MIA

3h 15mnonstop

8:00 am - 10:38 am

MIA

ORD

3h 38mnonstop

$83Frontier

Fri, Feb 27 - Sat, Feb 28

7:23 pm - 11:39 pm

ORD

MIA

3h 16mnonstop

7:12 am - 9:39 am

MIA

ORD

3h 27mnonstop

$84Spirit Airlines

Thu, Mar 5 - Sat, Mar 7

7:23 pm - 11:39 pm

ORD

MIA

3h 16mnonstop

7:12 am - 9:39 am

MIA

ORD

3h 27mnonstop

$85Spirit Airlines

Sun, Mar 8 - Wed, Mar 11

7:23 pm - 11:39 pm

ORD

MIA

3h 16mnonstop

7:12 am - 9:39 am

MIA

ORD

3h 27mnonstop

$86Spirit Airlines

Sun, Mar 1 - Tue, Mar 10

11:48 am - 4:03 pm

ORD

MIA

3h 15mnonstop

7:12 am - 9:39 am

MIA

ORD

3h 27mnonstop

$87Multiple Airlines

Sat, Feb 28 - Tue, Mar 10

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

$88Frontier

Thu, May 7 - Sun, May 10

11:18 am - 5:01 pm

ORD

EYW

4h 43m

1 stop

6:25 pm - 11:54 pm

EYW

ORD

6h 29m

1 stop

$298Delta

Tue, Mar 3 - Mon, Mar 9

9:52 am - 5:01 pm

ORD

EYW

6h 09m

1 stop

6:25 pm - 11:54 pm

EYW

ORD

6h 29m

1 stop

$299Delta

Wed, Mar 4 - Mon, Mar 9

Frontier flights from Chicago O'Hare Intl Airport to Florida Keys

Our best Frontier deals on Chicago O'Hare Intl Airport to Florida Keys flight tickets

Frontier

Feb 27

ORD10:48 amChicago O'Hare Intl

3h 15m

MIA3:03 pmMiami

Feb 28

MIA8:00 amMiami

3h 38m

ORD10:38 amChicago O'Hare Intl

$83

Frontier

May 7

ORD3:52 pmChicago O'Hare Intl

3h 19m

MIA8:11 pmMiami

May 11

MIA3:27 pmMiami

3h 38m

ORD6:05 pmChicago O'Hare Intl

$88

Frontier

Feb 27

ORD10:48 amChicago O'Hare Intl

3h 15m

MIA3:03 pmMiami

Mar 7

MIA7:15 amMiami

3h 38m

ORD9:53 amChicago O'Hare Intl

$89

Spirit Airlines flights from Chicago O'Hare Intl Airport to Florida Keys

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Florida Keys flight tickets

Spirit Airlines

Feb 24

ORD7:23 pmChicago O'Hare Intl

3h 16m

MIA11:39 pmMiami

Feb 26

MIA7:12 amMiami

3h 27m

ORD9:39 amChicago O'Hare Intl

$82

Spirit Airlines

Feb 23

ORD7:23 pmChicago O'Hare Intl

3h 16m

MIA11:39 pmMiami

Mar 26

MIA6:00 amMiami

3h 25m

ORD8:25 amChicago O'Hare Intl

$84

Spirit Airlines

Mar 8

ORD7:23 pmChicago O'Hare Intl

3h 16m

MIA11:39 pmMiami

Mar 12

MIA4:06 pmMiami

3h 25m

ORD6:31 pmChicago O'Hare Intl

$85

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 3/3

7:23 pm-11:39 pm

Nonstop3h 16m

Miami

Sat 3/7

7:15 am-9:53 am

Nonstop3h 38m

$81

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 3/9

9:05 pm-1:20 am

Nonstop3h 15m

Miami

Wed 3/11

7:12 am-9:39 am

Nonstop3h 27m

$82

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 2/27

10:48 am-3:03 pm

Nonstop3h 15m

Miami

Sat 2/28

8:00 am-10:38 am

Nonstop3h 38m

$83

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 3/5

7:23 pm-11:39 pm

Nonstop3h 16m

Miami

Sat 3/7

7:12 am-9:39 am

Nonstop3h 27m

$84

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 3/8

7:23 pm-11:39 pm

Nonstop3h 16m

Miami

Wed 3/11

7:12 am-9:39 am

Nonstop3h 27m

$85

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 3/1

7:23 pm-11:39 pm

Nonstop3h 16m

Miami

Tue 3/10

7:12 am-9:39 am

Nonstop3h 27m

$86

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/28

11:48 am-4:03 pm

Nonstop3h 15m

Miami

Tue 3/10

7:12 am-9:39 am

Nonstop3h 27m

$87

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/7

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

Sun 5/10

9:21 pm-11:59 pm

Nonstop3h 38m

$88

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 3/3

11:18 am-5:01 pm

1 stop4h 43m

Key West

Mon 3/9

6:25 pm-11:54 pm

1 stop6h 29m

$298

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 3/4

9:52 am-5:01 pm

1 stop6h 09m

Key West

Mon 3/9

6:25 pm-11:54 pm

1 stop6h 29m

$299

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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

Prices

Airlines

Other information

What is the cheapest month to fly to Florida Keys?

The month of January is another great option to travel to Florida Keys, with average flight prices from Chicago O'Hare Intl Airport averaging around $225.

What is the cheapest day to depart on your flight to Florida Keys?

The cheapest day to depart from Chicago O'Hare Intl Airport to Florida Keys is on a Monday when prices can be found for as low as $364. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $423.

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 O'Hare Intl Airport to Florida Keys in the evening for as low as $307. 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 $409.

What is the cheapest Chicago O'Hare Intl to Florida Keys flight route?

Fly from Chicago O'Hare Intl to Key West for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $262 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 O'Hare Intl Airport for as low as $213 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Florida Keys flights?

There are 3 cabin classes available to choose from on Chicago O'Hare Intl to Florida Keys flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago O'Hare Intl Airport to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Florida Keys.

Cheap Chicago O'Hare Intl Airport to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Florida Keys

Fastest flight time	3h 05m
Direct flights	Every day
Airports in Florida Keys	3 airports

The fastest flight from Chicago O'Hare Intl Airport to Florida Keys takes 3h 05m

Direct flights go from Chicago O'Hare Intl Airport to Florida Keys every day.

There are 3 airports in Florida Keys. From Chicago O'Hare Intl Airport there are direct flights to Key West (EYW), Miami (MIA).

Search flight deals

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Florida Keys?
Prices for flights from Chicago O'Hare Intl Airport to Florida Keys are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Florida Keys?
As of February 2026, there are 6 operators available to choose from for flights from Chicago O'Hare Intl Airport to Florida Keys.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Florida Keys?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Florida Keys.
What documentation or ID do you need to fly to Florida Keys?
The required travel and health documents for your Florida Keys trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Florida Keys. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Florida Keys?
momondo data reveals that the most frequently booked plane model on the route from Chicago O'Hare Intl Airport to Florida Keys is Boeing 737-800, representing 16.50% of all bookings. The subsequent popular models are Airbus A321neo at 16.13%, Boeing 737 MAX 8 at 8.25%, and Boeing 737-900 at 7.76%.

Best airlines flying from Chicago O'Hare Intl Airport to Florida Keys

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Florida Keys with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $145	Free Cancellation	Rating 6.3 8,451 reviews	Search Spirit Airlines flights
Delta	PriceFrom $248	Free Cancellation	Rating 7.9 8,203 reviews	Search Delta flights
United Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 9,289 reviews	Search United Airlines flights
American Airlines	PriceFrom $322	Free Cancellation	Rating 7.2 11,288 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Florida Keys?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Florida Keys for you.

Can I find flights from Chicago to Florida Keys with flexible booking policies on momondo?

Yes. All flights to Florida Keys from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Florida Keys?

Once you have performed a search for Chicago to Florida Keys flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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.

An easier way to manage your Florida Keys trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Popular cities in Florida Keys

Flights to New Yorkfrom $52

Flights to Los Angelesfrom $46

Flights to Miamifrom $43

Flights to Chicagofrom $52

Flights to Orlandofrom $51

Flights to San Franciscofrom $58

Flights to Las Vegasfrom $46

Flights to Washington, D.C.from $25

Flights to Bostonfrom $69

Flights to Atlantafrom $49

Flights to Dallasfrom $54

Flights to Seattlefrom $65

Cheap flights from Chicago O'Hare Intl Airport to Florida Keys from $43

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Find the cheapest flights from Chicago O'Hare Intl Airport to Florida Keys

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Frontier flights from Chicago O'Hare Intl Airport to Florida Keys

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momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Florida Keys that are best for you.

See travel insights to Florida Keys from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Florida Keys

What is the cheapest month to fly to Florida Keys?

What is the cheapest day to depart on your flight to Florida Keys?

What is the cheapest time of day to depart on your flight to Florida Keys?

What is the cheapest Chicago O'Hare Intl to Florida Keys flight route?

How far in advance should I book a flight to Florida Keys?

What cabin class options are available on Chicago O'Hare Intl to Florida Keys flights?

Can stopping save me money on Chicago O'Hare Intl Airport to Florida Keys flights?

What is the cheapest airline that flies from Chicago O'Hare Intl to Florida Keys?

What airlines fly to Florida Keys?

How many flights depart from Chicago O'Hare Intl Airport to Florida Keys on average per day?

How many flights depart from Chicago O'Hare Intl Airport to Florida Keys on average per week?

Cheap Chicago O'Hare Intl Airport to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Florida Keys

Fastest flight time

Direct flights

Airports in Florida Keys

Best airlines flying from Chicago O'Hare Intl Airport to Florida Keys

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Florida Keys with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Florida Keys?

Can I find flights from Chicago to Florida Keys with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Florida Keys?

I’m not ready to book a flight from Chicago to Florida Keys right now. Can momondo alert me if prices change?

An easier way to manage your Florida Keys trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Florida Keys

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