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 58% 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 day?

As of September 2026, there are 33 flights per day flying from Illinois to Florida Keys. The most common time of day flights depart is 11:00AM, with 80% of flights taking off at noon.

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

237 flights are operational weekly from Illinois to Florida Keys as of September 2026. The most popular departure day for this route is Wed, with 22% of flights per week taking off on this day.

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

Southwest, Delta, and United Airlines are the most popular carriers operating 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 September 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.

$54 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.

6:16 am - 3:25 pmMDW Chicago Midway-MIA Miami

8h 09m1 stop Atlanta Hartsfield-Jackson

5:05 am - 5:47 pmMIA Miami-MDW Chicago Midway

13h 42m1 stop Atlanta Hartsfield-Jackson

$172Frontier

Thu, Oct 29 - Sat, Oct 31

6:16 am - 9:31 pmMDW Chicago Midway-MIA Miami

14h 15m1 stop Atlanta Hartsfield-Jackson

5:05 am - 5:47 pmMIA Miami-MDW Chicago Midway

13h 42m1 stop Atlanta Hartsfield-Jackson

$174Frontier

Wed, Oct 28 - Sat, Oct 31

6:05 pm - 10:21 pmORD Chicago O'Hare Intl-MIA Miami

3h 16mnonstop

5:18 am - 8:00 amMIA Miami-ORD Chicago O'Hare Intl

3h 42mnonstop

$221American Airlines

Wed, Dec 2 - Wed, Dec 9

7:35 pm - 11:59 pmORD Chicago O'Hare Intl-MIA Miami

3h 24mnonstop

3:57 pm - 6:38 pmMIA Miami-ORD Chicago O'Hare Intl

3h 41mnonstop

$221American Airlines

Thu, Jan 7 - Mon, Jan 11

7:00 am - 11:11 amORD Chicago O'Hare Intl-MIA Miami

3h 11mnonstop

6:12 pm - 8:53 pmMIA Miami-ORD Chicago O'Hare Intl

3h 41mnonstop

$221United Airlines

Tue, Dec 15 - Wed, Dec 30

7:00 am - 11:11 amORD Chicago O'Hare Intl-MIA Miami

3h 11mnonstop

8:51 am - 11:25 amMIA Miami-ORD Chicago O'Hare Intl

3h 34mnonstop

$221United Airlines

Wed, Oct 28 - Sat, Oct 31

1:25 pm - 5:25 pmMDW Chicago Midway-MIA Miami

3h 00mnonstop

12:40 pm - 2:55 pmMIA Miami-MDW Chicago Midway

3h 15mnonstop

$221Southwest

Tue, Nov 10 - Tue, Nov 17

11:35 am - 3:45 pmMDW Chicago Midway-MIA Miami

3h 10mnonstop

12:35 pm - 2:40 pmMIA Miami-MDW Chicago Midway

3h 05mnonstop

$221Southwest

Wed, Oct 14 - Wed, Oct 28

6:35 pm - 9:24 amSTL Lambert-St Louis-EYW Key West

37h 49m2 stops Atlanta Hartsfield-Jackson Tampa

10:59 am - 11:16 pmEYW Key West-STL Lambert-St Louis

13h 17m1 stop Orlando

$227Multiple Airlines

Mon, Oct 26 - Mon, Nov 2

4:26 pm - 7:39 amSTL Lambert-St Louis-EYW Key West

14h 13m1 stop Orlando

12:01 pm - 5:40 pmEYW Key West-STL Lambert-St Louis

30h 39m2 stops Tampa Atlanta Hartsfield-Jackson

$247Multiple Airlines

Thu, Oct 29 - Thu, Nov 5

Cheap last minute flights

Enter your travel dates to find the best prices.

1:04 pm - 10:00 pmORD Chicago O'Hare Intl-MIA Miami

7h 56m1 stop Dallas/Fort Worth

11:25 am - 2:17 pmMIA Miami-ORD Chicago O'Hare Intl

27h 52m1 stop Houston George Bush Intcntl

$271Frontier

Sat, Sep 12 - Tue, Sep 15

6:30 am - 12:46 amORD Chicago O'Hare Intl-MIA Miami

17h 16m1 stop Denver Intl

2:37 pm - 8:29 pmMIA Miami-ORD Chicago O'Hare Intl

6h 52m1 stop Dallas/Fort Worth

$275Frontier

Wed, Sep 16 - Tue, Sep 29

3:50 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

17h 29m1 stop Orlando

10:04 am - 7:41 pmEYW Key West-ORD Chicago O'Hare Intl

10h 37m2 stops Tampa Dallas/Fort Worth

$357Multiple Airlines

Sat, Sep 12 - Sat, Sep 26

11:19 am - 7:05 pmMLI Moline Quad-City-MIA Miami

6h 46m1 stop Atlanta Hartsfield-Jackson

6:00 am - 10:13 amMIA Miami-MLI Moline Quad-City

5h 13m1 stop Atlanta Hartsfield-Jackson

$393Delta

Wed, Sep 16 - Wed, Sep 23

6:32 am - 2:51 pmMLI Moline Quad-City-MIA Miami

7h 19m1 stop Chicago O'Hare Intl

12:17 pm - 5:26 pmMIA Miami-MLI Moline Quad-City

6h 09m1 stop Chicago O'Hare Intl

$393United Airlines

Tue, Sep 15 - Tue, Sep 22

4:03 pm - 11:59 pmMLI Moline Quad-City-MIA Miami

6h 56m1 stop Charlotte Douglas

9:59 am - 4:27 pmMIA Miami-MLI Moline Quad-City

7h 28m2 stops Charlotte Douglas Chicago O'Hare Intl

$398American Airlines

Tue, Sep 15 - Tue, Sep 22

6:00 am - 3:38 pmMLI Moline Quad-City-MIA Miami

8h 38m2 stops Chicago O'Hare Intl Charlotte Douglas

8:52 am - 3:28 pmMIA Miami-MLI Moline Quad-City

7h 36m1 stop Charlotte Douglas

$398American Airlines

Wed, Sep 16 - Wed, Sep 23

6:20 am - 1:42 pmORD Chicago O'Hare Intl-MIA Miami

6h 22m1 stop Baltimore/Washington

6:54 pm - 10:50 amMIA Miami-ORD Chicago O'Hare Intl

40h 56m2 stops Charlotte Douglas Owensboro Daviess County

$416Multiple Airlines

Mon, Sep 14 - Tue, Sep 15

7:05 am - 1:05 pmSTL Lambert-St Louis-MIA Miami

5h 00m1 stop Atlanta Hartsfield-Jackson

6:25 pm - 11:42 pmMIA Miami-STL Lambert-St Louis

6h 17m1 stop Atlanta Hartsfield-Jackson

$447Delta

Wed, Sep 16 - Wed, Sep 16

8:13 am - 2:51 pmMLI Moline Quad-City-MIA Miami

5h 38m1 stop Chicago O'Hare Intl

11:30 am - 10:35 pmMIA Miami-MLI Moline Quad-City

12h 05m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

$461United Airlines

Sat, Sep 12 - Fri, Sep 18

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American Airlines flights from Illinois to Florida Keys

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

American Airlines

Dec 4

STL6:15 pmLambert-St Louis

2h 50m

MIA10:05 pmMiami

Dec 7

MIA5:18 amMiami

6h 29m

1 stop

STL10:47 amLambert-St Louis

$284

American Airlines

Oct 1

STL5:00 amLambert-St Louis

2h 44m

MIA8:44 amMiami

Oct 5

MIA4:45 pmMiami

7h 57m

1 stop

STL11:42 pmLambert-St Louis

$299

American Airlines

Dec 1

STL7:26 amLambert-St Louis

8h 09m

1 stop

EYW4:35 pmKey West

Dec 5

EYW4:49 pmKey West

8h 10m

1 stop

STL11:59 pmLambert-St Louis

$303

Frontier flights from Illinois to Florida Keys

Our best Frontier deals on Illinois to Florida Keys flight tickets

Frontier

Oct 29

MDW6:16 amChicago Midway

8h 09m

1 stop

MIA3:25 pmMiami

Oct 31

MIA5:05 amMiami

13h 42m

1 stop

MDW5:47 pmChicago Midway

$172

Frontier

Oct 28

MDW6:16 amChicago Midway

14h 15m

1 stop

MIA9:31 pmMiami

Oct 31

MIA5:05 amMiami

13h 42m

1 stop

MDW5:47 pmChicago Midway

$174

Frontier

Oct 10

ORD6:00 amChicago O'Hare Intl

14h 29m

1 stop

MIA9:29 pmMiami

Oct 12

MIA10:55 pmMiami

13h 37m

1 stop

ORD11:32 amChicago O'Hare Intl

$175

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Thu 10/29

6:16 am-3:25 pm

1 stop8h 09m

Miami

Sat 10/31

5:05 am-5:47 pm

1 stop13h 42m

$172

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Wed 10/28

6:16 am-9:31 pm

1 stop14h 15m

Miami

Sat 10/31

5:05 am-5:47 pm

1 stop13h 42m

$174

ChicagoMiami

ORD Chicago O'Hare Intl - MIA Miami

ORDMIA

Chicago O'Hare Intl

Wed 12/2

6:05 pm-10:21 pm

Nonstop3h 16m

Miami

Wed 12/9

5:18 am-8:00 am

Nonstop3h 42m

$221

ChicagoMiami

ORD Chicago O'Hare Intl - MIA Miami

ORDMIA

Chicago O'Hare Intl

Thu 1/7

7:35 pm-11:59 pm

Nonstop3h 24m

Miami

Mon 1/11

3:57 pm-6:38 pm

Nonstop3h 41m

$221

ChicagoMiami

ORD Chicago O'Hare Intl - MIA Miami

ORDMIA

Chicago O'Hare Intl

Tue 12/15

7:00 am-11:11 am

Nonstop3h 11m

Miami

Wed 12/30

6:12 pm-8:53 pm

Nonstop3h 41m

$221

ChicagoMiami

ORD Chicago O'Hare Intl - MIA Miami

ORDMIA

Chicago O'Hare Intl

Wed 10/28

7:00 am-11:11 am

Nonstop3h 11m

Miami

Sat 10/31

8:51 am-11:25 am

Nonstop3h 34m

$221

Quickest round-trip

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Tue 11/10

1:25 pm-5:25 pm

Nonstop3h 00m

Miami

Tue 11/17

12:40 pm-2:55 pm

Nonstop3h 15m

$221

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Wed 10/14

11:35 am-3:45 pm

Nonstop3h 10m

Miami

Wed 10/28

12:35 pm-2:40 pm

Nonstop3h 05m

$221

St. LouisKey West

STL Lambert-St Louis - EYW Key West

STLEYW

Lambert-St Louis

Mon 10/26

6:35 pm-9:24 am

2 stops37h 49m

Key West

Mon 11/2

10:59 am-11:16 pm

1 stop13h 17m

$227

St. LouisKey West

STL Lambert-St Louis - EYW Key West

STLEYW

Lambert-St Louis

Thu 10/29

4:26 pm-7:39 am

1 stop14h 13m

Key West

Thu 11/5

12:01 pm-5:40 pm

2 stops30h 39m

$247

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 February is another great option to travel to Florida Keys, with average flight prices from Illinois averaging around $284.

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 Saturday when prices can be found for as low as $445. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $510.

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 $390. 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 $476.

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 $306 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 $239 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

Best Price Found	$54
Fastest flight time	2h 35m
Direct flights	Every day
Airports in Florida Keys	3 airports

The best one-way flight to Florida Keys from Illinois in the past 72 hours is $54. The best round-trip flight deal from Illinois to Florida Keys found on momondo in the last 72 hours is $172.

The fastest flight from Illinois to Florida Keys takes 2h 35m

Direct flights go from Illinois to Florida Keys every day.

There are 3 airports in Florida Keys. From Illinois there are direct flights to 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 September 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 Airbus A321neo (17.03% of total bookings). The next most popular plane models are Boeing 737-800 (16.75%), Boeing 737-900 (9.73%), and Airbus A321-100/200 (8.73%).

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 $196	Free Cancellation	Rating 7.8 8,554 reviews	Search Delta flights
United Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 10,194 reviews	Search United Airlines flights
American Airlines	PriceFrom $268	Free Cancellation	Rating 7.1 12,045 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.