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

The number of flights available between Chicago and Florida Keys is 49 per day as of June 2026. The most frequent departure time is 10:00AM, with 100% of daily flights leaving at noon.

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

As of June 2026, 344 flights take off from Chicago and land in Florida Keys each week. The most common flight departure day for this route is Fri, with 17% 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 55% 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.

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

Southwest, Delta, and Allegiant Air are the most popular carriers operating from Chicago to Florida Keys

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 6 operators available for flights from Chicago to Florida Keys as of June 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.

$103 Cheap Flights from Chicago to Florida Keys in 2026

Discover deals from 900+ travel sites with momondo.

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.

6:05 pm - 10:27 pm

ORD

MIA

3h 22mnonstop

8:48 am - 2:53 pm

MIA

ORD

7h 05m

1 stop

$225United Airlines

Sat, Aug 1 - Tue, Aug 4

6:40 am - 6:22 pm

MDW

MIA

10h 42m

1 stop

6:45 am - 10:58 am

MIA

MDW

5h 13m

1 stop

$226Frontier

Sat, Oct 24 - Wed, Oct 28

11:45 am - 3:45 pm

MDW

MIA

3h 00mnonstop

11:45 am - 3:55 pm

MIA

MDW

5h 10m

1 stop

$227Southwest

Wed, Jul 22 - Tue, Jul 28

1:00 pm - 10:05 pm

MDW

MIA

8h 05m

2 stops

3:20 pm - 11:20 pm

MIA

MDW

9h 00m

1 stop

$228Southwest

Thu, Aug 6 - Thu, Aug 13

9:57 pm - 5:51 am

ORD

MIA

30h 54m

1 stop

10:15 pm - 5:37 am

MIA

ORD

32h 22m

1 stop

$228Frontier

Wed, Jul 15 - Tue, Jul 21

6:00 am - 4:16 pm

ORD

MIA

9h 16m

1 stop

12:30 pm - 3:13 pm

MIA

ORD

3h 43mnonstop

$231United Airlines

Tue, Jul 14 - Wed, Jul 22

7:07 pm - 11:25 pm

ORD

MIA

3h 18mnonstop

8:35 pm - 10:57 pm

MIA

ORD

3h 22mnonstop

$237American Airlines

Sat, Dec 12 - Mon, Dec 14

12:08 pm - 4:27 pm

ORD

EYW

3h 19mnonstop

4:58 pm - 7:50 pm

EYW

ORD

3h 52mnonstop

$309American Airlines

Sun, Aug 30 - Sun, Sep 6

12:46 pm - 7:57 pm

MDW

EYW

6h 11m

1 stop

6:15 pm - 10:36 pm

EYW

MDW

5h 21m

1 stop

$329Delta

Fri, Aug 14 - Tue, Aug 18

12:46 pm - 7:57 pm

MDW

EYW

6h 11m

1 stop

6:15 pm - 10:36 pm

EYW

MDW

5h 21m

1 stop

$354Delta

Thu, Aug 13 - Thu, Aug 20

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Frontier flights from Chicago to Florida Keys

Our best Frontier deals on Chicago to Florida Keys flight tickets

Frontier

Oct 24

MDW6:40 amChicago Midway

10h 42m

1 stop

MIA6:22 pmMiami

Oct 28

MIA6:45 amMiami

5h 13m

1 stop

MDW10:58 amChicago Midway

$226

Frontier

Jul 15

ORD9:57 pmChicago O'Hare Intl

30h 54m

1 stop

MIA5:51 amMiami

Jul 21

MIA10:15 pmMiami

32h 22m

1 stop

ORD5:37 amChicago O'Hare Intl

$228

Frontier

Jul 15

MDW6:05 amChicago Midway

6h 48m

1 stop

MIA1:53 pmMiami

Jul 22

MIA5:28 pmMiami

5h 35m

1 stop

MDW10:03 pmChicago Midway

$229

American Airlines flights from Chicago to Florida Keys

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

American Airlines

Dec 12

ORD7:07 pmChicago O'Hare Intl

3h 18m

MIA11:25 pmMiami

Dec 14

MIA8:35 pmMiami

3h 22m

ORD10:57 pmChicago O'Hare Intl

$237

American Airlines

Aug 13

ORD8:54 amChicago O'Hare Intl

5h 46m

1 stop

MIA3:40 pmMiami

Aug 18

MIA7:26 amMiami

3h 34m

ORD10:00 amChicago O'Hare Intl

$247

American Airlines

Dec 3

ORD4:45 pmChicago O'Hare Intl

3h 18m

MIA9:03 pmMiami

Dec 7

MIA10:11 pmMiami

3h 26m

ORD12:37 amChicago O'Hare Intl

$253

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 8/1

6:05 pm-10:27 pm

Nonstop3h 22m

Miami

Tue 8/4

8:48 am-2:53 pm

1 stop7h 05m

$225

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 10/24

6:40 am-6:22 pm

1 stop10h 42m

Miami

Wed 10/28

6:45 am-10:58 am

1 stop5h 13m

$226

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 7/22

11:45 am-3:45 pm

Nonstop3h 00m

Miami

Tue 7/28

11:45 am-3:55 pm

1 stop5h 10m

$227

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 8/6

1:00 pm-10:05 pm

2 stops8h 05m

Miami

Thu 8/13

3:20 pm-11:20 pm

1 stop9h 00m

$228

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 7/15

9:57 pm-5:51 am

1 stop30h 54m

Miami

Tue 7/21

10:15 pm-5:37 am

1 stop32h 22m

$228

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/14

6:00 am-4:16 pm

1 stop9h 16m

Miami

Wed 7/22

12:30 pm-3:13 pm

Nonstop3h 43m

$231

Quickest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 12/12

7:07 pm-11:25 pm

Nonstop3h 18m

Miami

Mon 12/14

8:35 pm-10:57 pm

Nonstop3h 22m

$237

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 8/30

12:08 pm-4:27 pm

Nonstop3h 19m

Key West

Sun 9/6

4:58 pm-7:50 pm

Nonstop3h 52m

$309

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/14

12:46 pm-7:57 pm

1 stop6h 11m

Key West

Tue 8/18

6:15 pm-10:36 pm

1 stop5h 21m

$329

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 8/13

12:46 pm-7:57 pm

1 stop6h 11m

Key West

Thu 8/20

6:15 pm-10:36 pm

1 stop5h 21m

$354

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 September is another great option to travel to Florida Keys, with average flight prices from Chicago averaging around $238.

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 $429. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $515.

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 $379. 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 $463.

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 from Chicago 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 $281 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 $223 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?

You could potentially save up to 23% on your flight if you consider stops on a Chicago to Florida Keys flight.

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 08m
Direct flights	Every day
Airports in Florida Keys	3 airports

The fastest flight from Chicago to Florida Keys takes 2h 08m

Direct flights go from Chicago to Florida Keys every day.

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

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Frequently asked questions about flying from Chicago to Florida Keys

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 6 operators available for flights from Chicago to Florida Keys as of June 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 Boeing 737-800, representing 19.17% of all bookings. The subsequent popular models are Airbus A321neo at 14.68%, Boeing 737-900 at 8.57%, and Airbus A321-100/200 at 7.66%.

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 $206	Free Cancellation	Rating 7.8 8,453 reviews	Search Delta flights
United Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 9,893 reviews	Search United Airlines flights
American Airlines	PriceFrom $308	Free Cancellation	Rating 7.1 11,769 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.