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

Delta, United Airlines, and Southwest are the most popular carriers operating from Illinois 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 Illinois according to our data. American Airlines is the first choice among our users, with 59% 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 flights depart from Illinois to Florida Keys on average per week?

340 flights are operational weekly from Illinois to Florida Keys as of June 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

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

As of June 2026, there are 48 flights per day flying from Illinois to Florida Keys. The most common time of day flights depart is 10:00AM, with 100% of flights taking off at noon.

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

Prices for flights from Illinois to Florida Keys are updated daily.

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

The number of operators available for flights from Illinois to Florida Keys is 6 as of June 2026.

How old do you have to be to fly from Illinois 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 Illinois to Florida Keys.

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

The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$81 Cheap Flights from Illinois to Florida Keys in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Illinois to Florida Keys

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:02 pm - 11:25 am

STL

EYW

17h 23m

1 stop

10:04 am - 9:40 am

EYW

STL

24h 36m

2 stops

$230Multiple Airlines

Sat, Aug 22 - Sat, Sep 12

7:05 am - 1:32 pm

ORD

MIA

5h 27m

1 stop

9:59 am - 3:59 pm

MIA

ORD

7h 00m

1 stop

$232Frontier

Wed, Aug 19 - Sat, Aug 22

11:45 am - 8:29 pm

MDW

MIA

7h 44m

1 stop

5:28 pm - 10:47 pm

MIA

MDW

6h 19m

1 stop

$232Frontier

Sat, Sep 5 - Tue, Sep 8

1:20 pm - 10:05 pm

MDW

MIA

7h 45m

2 stops

4:50 pm - 10:20 pm

MIA

MDW

6h 30m

2 stops

$233Southwest

Thu, Aug 13 - Thu, Aug 20

8:50 am - 8:45 pm

MDW

MIA

10h 55m

2 stops

7:00 am - 12:25 pm

MIA

MDW

6h 25m

2 stops

$239Southwest

Mon, Aug 10 - Thu, Aug 13

7:30 am - 11:55 am

ORD

MIA

3h 25mnonstop

1:26 pm - 6:41 pm

MIA

ORD

6h 15m

1 stop

$241United Airlines

Thu, Oct 15 - Tue, Oct 20

7:44 pm - 11:25 am

ORD

EYW

14h 41m

1 stop

10:04 am - 3:26 pm

EYW

ORD

30h 22m

2 stops

$262Multiple Airlines

Sat, Sep 5 - Wed, Sep 9

5:21 am - 9:09 am

STL

MIA

2h 48mnonstop

8:28 pm - 10:32 pm

MIA

STL

3h 04mnonstop

$281American Airlines

Tue, Nov 24 - Tue, Dec 1

11:35 am - 3:29 pm

STL

MIA

2h 54mnonstop

9:42 pm - 11:46 pm

MIA

STL

3h 04mnonstop

$283American Airlines

Sat, Sep 5 - Sat, Sep 12

5:40 am - 2:54 pm

MLI

MIA

8h 14m

1 stop

11:30 am - 11:14 pm

MIA

MLI

12h 44m

2 stops

$308United Airlines

Sat, Aug 15 - Sat, Aug 29

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Southwest flights from Illinois to Florida Keys

Our best Southwest deals on Illinois to Florida Keys flight tickets

Southwest

Aug 13

MDW1:20 pmChicago Midway

7h 45m

2 stops

MIA10:05 pmMiami

Aug 20

MIA4:50 pmMiami

6h 30m

2 stops

MDW10:20 pmChicago Midway

$233

Southwest

Aug 10

MDW8:50 amChicago Midway

10h 55m

2 stops

MIA8:45 pmMiami

Aug 13

MIA7:00 amMiami

6h 25m

2 stops

MDW12:25 pmChicago Midway

$239

Southwest

Aug 8

MDW8:05 amChicago Midway

10h 10m

2 stops

MIA7:15 pmMiami

Aug 10

MIA4:00 pmMiami

8h 45m

1 stop

MDW11:45 pmChicago Midway

$262

United Airlines flights from Illinois to Florida Keys

Our best United Airlines deals on Illinois to Florida Keys flight tickets

United Airlines

Jul 21

ORD6:05 pmChicago O'Hare Intl

3h 22m

MIA10:27 pmMiami

Jul 28

MIA4:53 pmMiami

8h 52m

1 stop

ORD12:45 amChicago O'Hare Intl

$245

United Airlines

Sep 5

ORD7:30 amChicago O'Hare Intl

3h 24m

MIA11:54 amMiami

Sep 12

MIA8:25 amMiami

9h 09m

1 stop

ORD4:34 pmChicago O'Hare Intl

$246

United Airlines

Jul 25

ORD6:05 pmChicago O'Hare Intl

3h 22m

MIA10:27 pmMiami

Aug 1

MIA6:30 amMiami

9h 21m

1 stop

ORD2:51 pmChicago O'Hare Intl

$249

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 8/22

5:02 pm-11:25 am

1 stop17h 23m

Key West

Sat 9/12

10:04 am-9:40 am

2 stops24h 36m

$230

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 8/19

7:05 am-1:32 pm

1 stop5h 27m

Miami

Sat 8/22

9:59 am-3:59 pm

1 stop7h 00m

$232

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/5

11:45 am-8:29 pm

1 stop7h 44m

Miami

Tue 9/8

5:28 pm-10:47 pm

1 stop6h 19m

$232

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 8/13

1:20 pm-10:05 pm

2 stops7h 45m

Miami

Thu 8/20

4:50 pm-10:20 pm

2 stops6h 30m

$233

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 8/10

8:50 am-8:45 pm

2 stops10h 55m

Miami

Thu 8/13

7:00 am-12:25 pm

2 stops6h 25m

$239

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 10/15

7:30 am-11:55 am

Nonstop3h 25m

Miami

Tue 10/20

1:26 pm-6:41 pm

1 stop6h 15m

$241

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/5

7:44 pm-11:25 am

1 stop14h 41m

Key West

Wed 9/9

10:04 am-3:26 pm

2 stops30h 22m

$262

Quickest round-trip

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Tue 11/24

5:21 am-9:09 am

Nonstop2h 48m

Miami

Tue 12/1

8:28 pm-10:32 pm

Nonstop3h 04m

$281

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Sat 9/5

11:35 am-3:29 pm

Nonstop2h 54m

Miami

Sat 9/12

9:42 pm-11:46 pm

Nonstop3h 04m

$283

MolineMiami

MLI - MIA

MLIMIA

Moline Quad-City

Sat 8/15

5:40 am-2:54 pm

1 stop8h 14m

Miami

Sat 8/29

11:30 am-11:14 pm

2 stops12h 44m

$308

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 Illinois 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 Illinois averaging around $238.

What is the cheapest day to depart on your flight to Florida Keys?

The cheapest day to depart from Illinois to Florida Keys is on a Monday when prices can be found for as low as $432. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $516.

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 Illinois 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 afternoon are often more expensive with an average ticket price of $467.

What is the cheapest Illinois to Florida Keys flight route?

Fly from Chicago O'Hare Intl to Key West for the best Illinois - Florida Keys flight prices

How far in advance should I book a flight from Illinois to Florida Keys?

You are more likely to see cheaper flights to Florida Keys from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $284 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida Keys from Illinois for as low as $224 on momondo.

What cabin class options are available on Illinois to Florida Keys flights?

There are 4 cabin classes available to choose from on Illinois 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 Illinois to Florida Keys flights?

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

Cheap Illinois to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Florida Keys

Fastest flight time	2h 08m
Direct flights	Every day
Airports in Florida Keys	3 airports

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

Direct flights go from Illinois to Florida Keys every day.

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

Search flight deals

Frequently asked questions about flying from Illinois to Florida Keys

When did momondo last update prices for flights from Illinois to Florida Keys?
Prices for flights from Illinois to Florida Keys are updated daily.
How many operators does momondo search for flights from Illinois to Florida Keys?
The number of operators available for flights from Illinois to Florida Keys is 6 as of June 2026.
How old do you have to be to fly from Illinois 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 Illinois to Florida Keys.
What documentation or ID do you need to fly to Florida Keys?
The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Illinois to Florida Keys?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Illinois to Florida Keys is Boeing 737-800 (19.21% of total bookings). The next most popular plane models are Airbus A321neo (14.88%), Boeing 737-900 (8.57%), and Airbus A321-100/200 (7.62%).

Best airlines flying from Illinois to Florida Keys

Compare and see reviews for airlines that fly from Illinois to Florida Keys with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $168	Free Cancellation	Rating 7.8 8,451 reviews	Search Delta flights
United Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 9,901 reviews	Search United Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.1 11,762 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Florida Keys?

It is quick and easy to find Illinois to Florida Keys flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Florida Keys that suits you.

Can I find flights from Illinois to Florida Keys with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to Florida Keys flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois to Florida Keys?

momondo helps you find the best flight between Illinois 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 Illinois to Florida Keys right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Illinois to Florida Keys flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.