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

Frontier, Spirit Airlines, and American Airlines are the most popular carriers operating from Chicago O'Hare Intl 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 O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 54% 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 operators does momondo search for flights from Chicago O'Hare Intl Airport to Florida Keys?

As of November 2025, there are 7 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.

$56 Cheap Flights from Chicago O'Hare Intl Airport to Florida Keys in 2025/26

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

As of November 2025, 38 flights take off from Chicago O'Hare Intl Airport and land in Florida Keys each day. The most common flight departure time for this route is 11:00AM, with 100% of daily flights taking off at noon.

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

As of November 2025, 267 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 Thu, with 16% of weekly flights taking off on this day.

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:14 pm - 8:23 amORD-MIA

10h 09m1 stop

2:19 pm - 10:11 pmMIA-ORD

8h 52m1 stop

$113Spirit Airlines

Find Deal

Tue, Dec 9 - Wed, Dec 10

4:20 pm - 12:46 amORD-MIA

7h 26m1 stop

4:08 pm - 6:36 pmMIA-ORD

3h 28mnonstop

$114Multiple Airlines

Find Deal

Fri, Dec 5 - Tue, Dec 9

7:41 pm - 11:57 pmORD-MIA

3h 16mnonstop

2:10 pm - 8:09 pmMIA-ORD

6h 59m1 stop

$115Spirit Airlines

Find Deal

Fri, Dec 5 - Wed, Dec 10

1:52 pm - 8:54 pmORD-MIA

6h 02m1 stop

5:45 am - 8:09 amMIA-ORD

3h 24mnonstop

$116Spirit Airlines

Find Deal

Thu, Dec 11 - Sun, Jan 11

6:05 pm - 10:21 pmORD-MIA

3h 16mnonstop

5:30 am - 7:54 amMIA-ORD

3h 24mnonstop

$117Spirit Airlines

Find Deal

Sat, Jan 3 - Sat, Jan 10

6:11 am - 3:39 pmORD-MIA

8h 28m1 stop

2:10 pm - 8:09 pmMIA-ORD

6h 59m1 stop

$118Multiple Airlines

Find Deal

Sat, Dec 6 - Tue, Dec 9

5:30 am - 11:43 amORD-EYW

5h 13m1 stop

6:10 pm - 10:43 pmEYW-ORD

5h 33m1 stop

$294Delta

Find Deal

Mon, Dec 8 - Sat, Dec 13

1:14 pm - 7:53 pmORD-EYW

5h 39m1 stop

6:10 pm - 10:43 pmEYW-ORD

5h 33m1 stop

$296Delta

Find Deal

Thu, Nov 27 - Tue, Dec 2

7:55 am - 12:34 pmORD-EYW

3h 39mnonstop

12:22 pm - 3:07 pmEYW-ORD

3h 45mnonstop

$299United Airlines

Find Deal

Fri, Dec 19 - Mon, Dec 22

11:05 am - 3:24 pmORD-EYW

3h 19mnonstop

4:10 pm - 6:43 pmEYW-ORD

3h 33mnonstop

$301United Airlines

Find Deal

Tue, Dec 16 - Mon, Dec 22

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

Dec 9

ORD9:14 pmChicago O'Hare Intl

10h 09m

1 stop

MIA8:23 amMiami

Dec 10

MIA2:19 pmMiami

8h 52m

1 stop

ORD10:11 pmChicago O'Hare Intl

$113

Find similar

Spirit Airlines

Dec 5

ORD7:41 pmChicago O'Hare Intl

3h 16m

MIA11:57 pmMiami

Dec 10

MIA2:10 pmMiami

6h 59m

1 stop

ORD8:09 pmChicago O'Hare Intl

$115

Find similar

Spirit Airlines

Dec 11

ORD1:52 pmChicago O'Hare Intl

6h 02m

1 stop

MIA8:54 pmMiami

Jan 11

MIA5:45 amMiami

3h 24m

ORD8:09 amChicago O'Hare Intl

$116

Find similar

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

Jan 9

ORD4:20 pmChicago O'Hare Intl

26h 31m

1 stop

MIA7:51 pmMiami

Jan 13

MIA5:15 amMiami

7h 53m

1 stop

ORD12:08 pmChicago O'Hare Intl

$124

Find similar

Frontier

Dec 17

ORD8:00 amChicago O'Hare Intl

7h 28m

1 stop

MIA4:28 pmMiami

Dec 21

MIA10:20 amMiami

11h 19m

1 stop

ORD8:39 pmChicago O'Hare Intl

$127

Find similar

Frontier

Feb 21

ORD6:00 pmChicago O'Hare Intl

5h 56m

1 stop

MIA12:56 amMiami

Mar 1

MIA5:35 amMiami

6h 14m

1 stop

ORD10:49 amChicago O'Hare Intl

$128

Find similar

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 12/9

9:14 pm-8:23 am

1 stop10h 09m

Miami

Wed 12/10

2:19 pm-10:11 pm

1 stop8h 52m

$113

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 12/5

4:20 pm-12:46 am

1 stop7h 26m

Miami

Tue 12/9

4:08 pm-6:36 pm

Nonstop3h 28m

$114

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 12/5

7:41 pm-11:57 pm

Nonstop3h 16m

Miami

Wed 12/10

2:10 pm-8:09 pm

1 stop6h 59m

$115

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 12/11

1:52 pm-8:54 pm

1 stop6h 02m

Miami

Sun 1/11

5:45 am-8:09 am

Nonstop3h 24m

$116

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 1/3

6:05 pm-10:21 pm

Nonstop3h 16m

Miami

Sat 1/10

5:30 am-7:54 am

Nonstop3h 24m

$117

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 12/6

6:11 am-3:39 pm

1 stop8h 28m

Miami

Tue 12/9

2:10 pm-8:09 pm

1 stop6h 59m

$118

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 12/8

5:30 am-11:43 am

1 stop5h 13m

Key West

Sat 12/13

6:10 pm-10:43 pm

1 stop5h 33m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 11/27

1:14 pm-7:53 pm

1 stop5h 39m

Key West

Tue 12/2

6:10 pm-10:43 pm

1 stop5h 33m

$296

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 12/19

7:55 am-12:34 pm

Nonstop3h 39m

Key West

Mon 12/22

12:22 pm-3:07 pm

Nonstop3h 45m

$299

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 12/16

11:05 am-3:24 pm

Nonstop3h 19m

Key West

Mon 12/22

4:10 pm-6:43 pm

Nonstop3h 33m

$301

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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 August 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 $415. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $455.

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 $275. 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 afternoon are often more expensive with an average ticket price of $455.

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 $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 O'Hare Intl Airport for as low as $216 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 01m
Direct flights	Every day
Airports in Florida Keys	2 airports

The fastest flight from Chicago O'Hare Intl Airport to Florida Keys takes 3h 01m

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

There are 2 airports near Florida Keys: 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 November 2025, there are 7 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 20.14% of all bookings. The subsequent popular models are Airbus A321neo at 13.94%, Boeing 737-900 at 9.13%, and Airbus A320neo at 7.02%.

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
Delta	PriceFrom $218	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
United Airlines	PriceFrom $255	Free Cancellation	Rating 7.4 9,017 reviews	Search United Airlines flights
American Airlines	PriceFrom $314	Free Cancellation	Rating 7.2 11,051 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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Find better results for your trip to Florida Keys

Popular cities in Florida Keys

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Flights to Washington, D.C.from $40

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Chicago O'Hare Intl Airport flight routes

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Flights from Chicago O'Hare Intl to New York LaGuardia

Flights from Chicago O'Hare Intl to Charlotte Douglas

Flights from Chicago O'Hare Intl to Raleigh-Durham

Cheap flights from Chicago O'Hare Intl Airport to Florida Keys from $56

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

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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

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

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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

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 August 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 $415. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $455.

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?

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?

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.

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

Frontier, Spirit Airlines, and American Airlines are the most popular carriers operating 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?

As of November 2025, 38 flights take off from Chicago O'Hare Intl Airport and land in Florida Keys each day. The most common flight departure time for this route is 11:00AM, with 100% of daily flights taking off at noon.

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

As of November 2025, 267 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 Thu, with 16% of weekly flights taking off on this day.

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

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Florida Keys?

How many operators does momondo search 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?

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

What is the most popular plane model from Chicago O'Hare Intl Airport to 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

Popular cities in Florida Keys

Popular flights according to clicks in the last 7 days on momondo