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

As of November 2025, 241 flights take off from Chicago and land in Florida Keys each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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

The number of flights available between Chicago and Florida Keys is 34 per day as of November 2025. The most frequent departure time is 11:00AM, with 100% of daily flights leaving at noon.

What is the cheapest airline that flies from Chicago to Florida Keys?

Frontier, Spirit Airlines, and United Airlines 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 53% 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.

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 November 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.

$56 Cheap Flights from Chicago to Florida Keys in 2025/26

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Cheap round-trip flights

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1:35 pm - 5:50 pmORD-MIA

3h 15mnonstop

10:15 am - 12:30 pmMIA-ORD

3h 15mnonstop

$108Spirit Airlines

Find Deal

Mon, Jan 26 - Sun, Feb 1

5:57 pm - 10:03 pmMDW-MIA

3h 06mnonstop

7:26 pm - 9:53 pmMIA-MDW

3h 27mnonstop

$108Frontier

Find Deal

Sat, Nov 29 - Thu, Dec 4

6:05 pm - 10:21 pmORD-MIA

3h 16mnonstop

6:05 am - 10:49 amMIA-ORD

5h 44m1 stop

$109Multiple Airlines

Find Deal

Mon, Jan 5 - Wed, Jan 7

9:40 am - 1:45 pmMDW-MIA

3h 05mnonstop

2:35 pm - 4:50 pmMIA-MDW

3h 15mnonstop

$157Southwest

Find Deal

Mon, Jan 19 - Fri, Jan 23

6:00 am - 1:48 pmMDW-EYW

6h 48m1 stop

6:07 pm - 10:44 pmEYW-MDW

5h 37m1 stop

$294Delta

Find Deal

Tue, Feb 24 - Wed, Mar 4

11:00 am - 3:19 pmORD-EYW

3h 19mnonstop

4:00 pm - 6:46 pmEYW-ORD

3h 46mnonstop

$300United Airlines

Find Deal

Tue, Nov 18 - Mon, Nov 24

6:02 am - 2:04 pmORD-EYW

7h 02m1 stop

4:00 pm - 6:46 pmEYW-ORD

3h 46mnonstop

$310United Airlines

Find Deal

Tue, Nov 18 - Mon, Nov 24

8:50 am - 1:20 pmORD-EYW

3h 30mnonstop

3:18 pm - 8:34 pmEYW-ORD

6h 16m1 stop

$313American Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

7:35 pm - 7:42 pmORD-EYW

23h 07m2 stops

7:10 am - 1:39 pmEYW-ORD

7h 29m1 stop

$317Delta

Find Deal

Fri, Feb 20 - Tue, Feb 24

6:00 am - 4:05 pmORD-EYW

9h 05m1 stop

5:24 pm - 12:13 amEYW-ORD

7h 49m1 stop

$323American Airlines

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Wed, Mar 25 - Tue, Mar 31

Spirit Airlines flights from Chicago to Florida Keys

Our best Spirit Airlines deals on Chicago to Florida Keys flight tickets

Spirit Airlines

Jan 26

ORD1:35 pmChicago O'Hare Intl

3h 15m

MIA5:50 pmMiami

Feb 1

MIA10:15 amMiami

3h 15m

ORD12:30 pmChicago O'Hare Intl

$108

Find similar

Spirit Airlines

Dec 10

ORD7:41 pmChicago O'Hare Intl

3h 16m

MIA11:57 pmMiami

Dec 15

MIA4:08 pmMiami

3h 28m

ORD6:36 pmChicago O'Hare Intl

$115

Find similar

Spirit Airlines

Jan 28

ORD7:35 amChicago O'Hare Intl

13h 24m

1 stop

MIA9:59 pmMiami

Feb 2

MIA10:15 amMiami

3h 15m

ORD12:30 pmChicago O'Hare Intl

$116

Find similar

Frontier flights from Chicago to Florida Keys

Our best Frontier deals on Chicago to Florida Keys flight tickets

Frontier

Nov 29

MDW5:57 pmChicago Midway

3h 06m

MIA10:03 pmMiami

Dec 4

MIA7:26 pmMiami

3h 27m

MDW9:53 pmChicago Midway

$108

Find similar

Frontier

Nov 26

MDW5:57 pmChicago Midway

3h 06m

MIA10:03 pmMiami

Dec 6

MIA9:38 amMiami

5h 21m

1 stop

MDW1:59 pmChicago Midway

$109

Find similar

Frontier

Jan 7

ORD6:11 pmChicago O'Hare Intl

5h 35m

1 stop

MIA12:46 amMiami

Jan 10

MIA7:09 pmMiami

5h 52m

1 stop

ORD12:01 amChicago O'Hare Intl

$110

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/26

1:35 pm-5:50 pm

Nonstop3h 15m

Miami

Sun 2/1

10:15 am-12:30 pm

Nonstop3h 15m

$108

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 11/29

5:57 pm-10:03 pm

Nonstop3h 06m

Miami

Thu 12/4

7:26 pm-9:53 pm

Nonstop3h 27m

$108

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/5

6:05 pm-10:21 pm

Nonstop3h 16m

Miami

Wed 1/7

6:05 am-10:49 am

1 stop5h 44m

$109

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 1/19

9:40 am-1:45 pm

Nonstop3h 05m

Miami

Fri 1/23

2:35 pm-4:50 pm

Nonstop3h 15m

$157

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 2/24

6:00 am-1:48 pm

1 stop6h 48m

Key West

Wed 3/4

6:07 pm-10:44 pm

1 stop5h 37m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 11/18

11:00 am-3:19 pm

Nonstop3h 19m

Key West

Mon 11/24

4:00 pm-6:46 pm

Nonstop3h 46m

$300

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 11/18

6:02 am-2:04 pm

1 stop7h 02m

Key West

Mon 11/24

4:00 pm-6:46 pm

Nonstop3h 46m

$310

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 12/9

8:50 am-1:20 pm

Nonstop3h 30m

Key West

Sat 12/13

3:18 pm-8:34 pm

1 stop6h 16m

$313

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 2/20

7:35 pm-7:42 pm

2 stops23h 07m

Key West

Tue 2/24

7:10 am-1:39 pm

1 stop7h 29m

$317

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 3/25

6:00 am-4:05 pm

1 stop9h 05m

Key West

Tue 3/31

5:24 pm-12:13 am

1 stop7h 49m

$323

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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

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 averaging around $234.

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 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 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 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 $270 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 $218 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.

Can stopping save me money on Chicago to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Chicago to Florida Keys.

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

Fastest flight time	3h 00m
Direct flights	Every day
Airports in Florida Keys	1 airport

The fastest flight from Chicago to Florida Keys takes 3h 00m

Direct flights go from Chicago to Florida Keys every day.

There is 1 airport near Florida Keys: Miami (MIA)

Search flight deals

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 November 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 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 7.30%.

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
Delta	PriceFrom $218	Free Cancellation	Rating 7.9 8,003 reviews	Search Delta flights
United Airlines	PriceFrom $255	Free Cancellation	Rating 7.4 9,002 reviews	Search United Airlines flights
American Airlines	PriceFrom $314	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights

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.

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

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Flights to Bostonfrom $40

Flights to Atlantafrom $40

Flights to Dallasfrom $49

Flights to Seattlefrom $68

Cheap flights from Chicago to Florida Keys from $56

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 12/10. 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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Big names and deals

Filter for what you want

Filter for what you want

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Spirit Airlines flights from Chicago to Florida Keys

Our best Spirit Airlines deals on Chicago to Florida Keys flight tickets

Frontier flights from Chicago to Florida Keys

Our best Frontier deals on Chicago to Florida Keys flight tickets

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See travel insights to Florida Keys from

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 January is another great option to travel to Florida Keys, with average flight prices from Chicago averaging around $234.

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 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 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?

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.

Can stopping save me money on Chicago to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Chicago to Florida Keys.

What is the cheapest airline that flies from Chicago to Florida Keys?

Frontier, Spirit Airlines, and United Airlines are the most popular carriers operating from Chicago to Florida Keys

What airlines fly to Florida Keys?

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

The number of flights available between Chicago and Florida Keys is 34 per day as of November 2025. The most frequent departure time is 11:00AM, with 100% of daily flights leaving at noon.

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

As of November 2025, 241 flights take off from Chicago and land in Florida Keys each week. The most common flight departure day for this route is Mon, with 17% 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

Fastest flight time

Direct flights

Airports in Florida Keys

When did momondo last update prices for flights from Chicago to Florida Keys?

How many operators does momondo search for flights from Chicago to Florida Keys?

How old do you have to be to fly from Chicago to Florida Keys?

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

What is the most popular plane model from Chicago to Florida Keys?

Best airlines flying from Chicago to Florida Keys

Compare and see reviews for airlines that fly from Chicago 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