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

The number of flights available between Chicago and Florida Keys is 50 per day as of April 2026. The most frequent departure time is 10:00AM, with 83% of daily flights leaving at noon.

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

Spirit Airlines, Southwest, and Frontier 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 April 2026, 351 flights take off from Chicago and land in Florida Keys each week. The most common flight departure day for this route is Sat, 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 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 April 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.

$49 Cheap Flights from Chicago to Florida Keys in 2026

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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.

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

6:30 am - 5:11 pm

MIA

ORD

11h 41m

1 stop

$101Multiple Airlines

Sat, Apr 25 - Sat, May 2

9:20 am - 1:28 pm

ORD

MIA

3h 08mnonstop

9:30 pm - 11:56 pm

MIA

ORD

3h 26mnonstop

$102Spirit Airlines

Mon, May 11 - Fri, May 15

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

$103Frontier

Thu, Apr 23 - Thu, Apr 30

4:28 pm - 12:49 am

ORD

MIA

7h 21m

1 stop

2:13 pm - 4:50 pm

MIA

ORD

3h 37mnonstop

$104Frontier

Sat, May 2 - Thu, May 7

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

$105Frontier

Thu, Apr 23 - Sat, Apr 25

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

5:05 am - 10:23 am

MIA

ORD

6h 18m

1 stop

$106Multiple Airlines

Sat, Apr 25 - Fri, May 1

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

11:23 am - 7:51 pm

MIA

ORD

9h 28m

1 stop

$107Frontier

Sat, May 2 - Tue, May 5

11:22 am - 3:49 pm

ORD

EYW

3h 27mnonstop

5:37 pm - 12:38 am

EYW

ORD

8h 01m

1 stop

$319American Airlines

Wed, Jun 3 - Wed, Jun 10

6:05 am - 1:28 pm

MDW

EYW

6h 23m

1 stop

6:24 pm - 10:17 pm

EYW

MDW

4h 53m

1 stop

$329Delta

Tue, Jun 9 - Wed, Jun 24

6:05 am - 1:38 pm

MDW

EYW

6h 33m

1 stop

6:18 pm - 10:15 pm

EYW

MDW

4h 57m

1 stop

$349Delta

Tue, Jun 30 - Wed, Jul 8

Frontier flights from Chicago to Florida Keys

Our best Frontier deals on Chicago to Florida Keys flight tickets

Frontier

Apr 23

ORD3:52 pmChicago O'Hare Intl

3h 19m

MIA8:11 pmMiami

Apr 30

MIA9:21 pmMiami

3h 38m

ORD11:59 pmChicago O'Hare Intl

$103

Frontier

May 2

ORD4:28 pmChicago O'Hare Intl

7h 21m

1 stop

MIA12:49 amMiami

May 7

MIA2:13 pmMiami

3h 37m

ORD4:50 pmChicago O'Hare Intl

$104

Frontier

Apr 23

ORD3:52 pmChicago O'Hare Intl

3h 19m

MIA8:11 pmMiami

Apr 25

MIA9:21 pmMiami

3h 38m

ORD11:59 pmChicago O'Hare Intl

$105

Spirit Airlines flights from Chicago to Florida Keys

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

Spirit Airlines

May 11

ORD9:20 amChicago O'Hare Intl

3h 08m

MIA1:28 pmMiami

May 15

MIA9:30 pmMiami

3h 26m

ORD11:56 pmChicago O'Hare Intl

$102

Spirit Airlines

Apr 27

ORD7:50 amChicago O'Hare Intl

3h 08m

MIA11:58 amMiami

May 1

MIA10:41 amMiami

3h 24m

ORD1:05 pmChicago O'Hare Intl

$111

Spirit Airlines

Apr 30

ORD11:28 amChicago O'Hare Intl

10h 03m

1 stop

MIA10:31 pmMiami

May 1

MIA10:41 amMiami

3h 24m

ORD1:05 pmChicago O'Hare Intl

$113

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 4/25

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

Sat 5/2

6:30 am-5:11 pm

1 stop11h 41m

$101

Quickest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 5/11

9:20 am-1:28 pm

Nonstop3h 08m

Miami

Fri 5/15

9:30 pm-11:56 pm

Nonstop3h 26m

$102

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 4/23

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

Thu 4/30

9:21 pm-11:59 pm

Nonstop3h 38m

$103

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/2

4:28 pm-12:49 am

1 stop7h 21m

Miami

Thu 5/7

2:13 pm-4:50 pm

Nonstop3h 37m

$104

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 4/23

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

Sat 4/25

9:21 pm-11:59 pm

Nonstop3h 38m

$105

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 4/25

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

Fri 5/1

5:05 am-10:23 am

1 stop6h 18m

$106

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/2

3:52 pm-8:11 pm

Nonstop3h 19m

Miami

Tue 5/5

11:23 am-7:51 pm

1 stop9h 28m

$107

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 6/3

11:22 am-3:49 pm

Nonstop3h 27m

Key West

Wed 6/10

5:37 pm-12:38 am

1 stop8h 01m

$319

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 6/9

6:05 am-1:28 pm

1 stop6h 23m

Key West

Wed 6/24

6:24 pm-10:17 pm

1 stop4h 53m

$329

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 6/30

6:05 am-1:38 pm

1 stop6h 33m

Key West

Wed 7/8

6:18 pm-10:15 pm

1 stop4h 57m

$349

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 October is another great option to travel to Florida Keys, with average flight prices from Chicago averaging around $235.

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 $348. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $408.

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 $282. 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 $398.

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 $214 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

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 8 operators available for flights from Chicago to Florida Keys as of April 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 16.85% of all bookings. The subsequent popular models are Boeing 737-800 at 15.07%, Airbus A321-100/200 at 8.37%, and Boeing 737-900 at 7.72%.

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 8,608 reviews	Search Spirit Airlines flights
Delta	PriceFrom $248	Free Cancellation	Rating 7.9 8,405 reviews	Search Delta flights
United Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 9,569 reviews	Search United Airlines flights
American Airlines	PriceFrom $309	Free Cancellation	Rating 7.1 11,569 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.