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

The number of flights available between Chicago and Florida Keys is 51 per day as of February 2026. The most frequent departure time is 10:00AM, with 52% of daily flights leaving at noon.

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

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

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

As of February 2026, 363 flights take off from Chicago and land in Florida Keys each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.

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 54% 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.

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 8 operators available for flights from Chicago to Florida Keys as of February 2026.

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.

$41 Cheap Flights from Chicago to Florida Keys in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Florida Keys

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:15 pm - 11:34 pm

ORD

MIA

3h 19mnonstop

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

$81Frontier

Mo, Apr 27 - So, Mai 10

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

$82Frontier

So, Apr 19 - So, Apr 26

6:00 am - 10:13 am

MDW

MIA

3h 13mnonstop

11:13 am - 1:41 pm

MIA

MDW

3h 28mnonstop

$83Frontier

So, Mrz 8 - Sa, Mrz 14

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

$83Frontier

So, Mai 10 - Sa, Mai 16

9:18 am - 1:36 pm

ORD

MIA

3h 18mnonstop

4:06 pm - 6:31 pm

MIA

ORD

3h 25mnonstop

$84Spirit Airlines

Mo, Mrz 9 - Do, Mrz 12

7:23 pm - 11:39 pm

ORD

MIA

3h 16mnonstop

7:12 am - 9:39 am

MIA

ORD

3h 27mnonstop

$85Spirit Airlines

Di, Mrz 3 - Di, Mrz 10

7:25 pm - 11:41 pm

ORD

MIA

3h 16mnonstop

6:00 am - 8:38 am

MIA

ORD

3h 38mnonstop

$90Multiple Airlines

Di, Mrz 10 - Mo, Mrz 16

6:55 pm - 9:06 am

ORD

EYW

37h 11m

2 stops

12:25 pm - 7:51 pm

EYW

ORD

8h 26m

1 stop

$293Multiple Airlines

Fr, Mrz 13 - Mi, Mrz 18

12:52 pm - 7:40 pm

MDW

EYW

5h 48m

1 stop

6:23 pm - 10:28 pm

EYW

MDW

5h 05m

1 stop

$299Delta

Mi, Apr 15 - Di, Apr 21

10:41 am - 5:23 pm

MDW

EYW

5h 42m

1 stop

6:18 pm - 10:28 pm

EYW

MDW

5h 10m

1 stop

$304Delta

Di, Apr 28 - Sa, Mai 2

Spirit Airlines flights from Chicago to Florida Keys

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

Spirit Airlines

Mar 9

ORD9:18 amChicago O'Hare Intl

3h 18m

MIA1:36 pmMiami

Mar 12

MIA4:06 pmMiami

3h 25m

ORD6:31 pmChicago O'Hare Intl

$84

Spirit Airlines

Mar 3

ORD7:23 pmChicago O'Hare Intl

3h 16m

MIA11:39 pmMiami

Mar 10

MIA7:12 amMiami

3h 27m

ORD9:39 amChicago O'Hare Intl

$85

Spirit Airlines

Mar 14

ORD4:51 pmChicago O'Hare Intl

3h 06m

MIA8:57 pmMiami

Mar 15

MIA6:00 amMiami

3h 25m

ORD8:25 amChicago O'Hare Intl

$86

Frontier flights from Chicago to Florida Keys

Our best Frontier deals on Chicago to Florida Keys flight tickets

Frontier

Apr 27

ORD7:15 pmChicago O'Hare Intl

3h 19m

MIA11:34 pmMiami

May 10

MIA9:21 pmMiami

3h 38m

ORD11:59 pmChicago O'Hare Intl

$81

Frontier

Apr 19

ORD3:52 pmChicago O'Hare Intl

3h 19m

MIA8:11 pmMiami

Apr 26

MIA9:21 pmMiami

3h 38m

ORD11:59 pmChicago O'Hare Intl

$82

Frontier

May 10

ORD3:52 pmChicago O'Hare Intl

3h 19m

MIA8:11 pmMiami

May 16

MIA9:21 pmMiami

3h 38m

ORD11:59 pmChicago O'Hare Intl

$83

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mo 4/27

7:15 pm-11:34 pm

Nonstop3h 19m

Miami

So 5/10

9:21 pm-11:59 pm

Nonstop3h 38m

$81

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

So 4/19

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

So 4/26

9:21 pm-11:59 pm

Nonstop3h 38m

$82

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

So 3/8

6:00 am-10:13 am

Nonstop3h 13m

Miami

Sa 3/14

11:13 am-1:41 pm

Nonstop3h 28m

$83

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

So 5/10

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

Sa 5/16

9:21 pm-11:59 pm

Nonstop3h 38m

$83

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mo 3/9

9:18 am-1:36 pm

Nonstop3h 18m

Miami

Do 3/12

4:06 pm-6:31 pm

Nonstop3h 25m

$84

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Di 3/3

7:23 pm-11:39 pm

Nonstop3h 16m

Miami

Di 3/10

7:12 am-9:39 am

Nonstop3h 27m

$85

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Di 3/10

7:25 pm-11:41 pm

Nonstop3h 16m

Miami

Mo 3/16

6:00 am-8:38 am

Nonstop3h 38m

$90

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fr 3/13

6:55 pm-9:06 am

2 stops37h 11m

Key West

Mi 3/18

12:25 pm-7:51 pm

1 stop8h 26m

$293

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mi 4/15

12:52 pm-7:40 pm

1 stop5h 48m

Key West

Di 4/21

6:23 pm-10:28 pm

1 stop5h 05m

$299

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Di 4/28

10:41 am-5:23 pm

1 stop5h 42m

Key West

Sa 5/2

6:18 pm-10:28 pm

1 stop5h 10m

$304

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 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 $237.

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 $354. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $418.

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 $300. 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 $405.

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 $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 for as low as $210 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	2h 55m
Direct flights	Every day
Airports in Florida Keys	3 airports

The fastest flight from Chicago to Florida Keys takes 2h 55m

Direct flights go from Chicago to Florida Keys every day.

There are 3 airports in Florida Keys. From Chicago there are direct flights to 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 8 operators available for flights from Chicago to Florida Keys as of February 2026.
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 Airbus A321neo, representing 16.30% of all bookings. The subsequent popular models are Boeing 737-800 at 16.02%, Boeing 737-900 at 7.76%, and Boeing 737 MAX 8 at 7.25%.

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
Spirit Airlines	PriceFrom $145	Free Cancellation	Rating 6.3 8,478 reviews	Search Spirit Airlines flights
Delta	PriceFrom $248	Free Cancellation	Rating 7.9 8,215 reviews	Search Delta flights
United Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 9,325 reviews	Search United Airlines flights
American Airlines	PriceFrom $322	Free Cancellation	Rating 7.2 11,321 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

So 3/22

So 3/29

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Florida Keys

Popular cities

Other flights from Chicago

Airlines

Complete your trip

Feeling lucky

Popular cities in Florida Keys

Flights to New Yorkfrom $54

Flights to Los Angelesfrom $51

Flights to Miamifrom $49

Flights to Orlandofrom $49

Flights to Chicagofrom $53

Flights to San Franciscofrom $63

Flights to Las Vegasfrom $51

Flights to Washington, D.C.from $56

Flights to Bostonfrom $72

Flights to Atlantafrom $49

Flights to Dallasfrom $53

Flights to Seattlefrom $55

Cheap flights from Chicago to Florida Keys from $41

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 5/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Florida Keys

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

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

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to Florida Keys that are best for you.

See travel insights to Florida Keys from

How to get the cheapest flight ticket from Chicago 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 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 to Florida Keys flights?

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

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

What airlines fly to Florida Keys?

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

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

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

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

Chicago flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Florida Keys

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Complete your trip to Florida Keys

Explore popular destinations other users love

According to popular flight searches on momondo this year