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

The number of flights available between Florida Keys and Illinois is 47 per day as of May 2026. The most frequent departure time is 1:00PM, with 82% of daily flights leaving in the afternoon.

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

As of May 2026, there are 330 flights per week flying from Florida Keys to Illinois. The most common day of the week flights depart is Sun, with 20% of flights taking off on this day.

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

Southwest, Delta, and United Airlines are the most popular carriers operating from Florida Keys to Illinois

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

Prices for flights from Florida Keys to Illinois are refreshed on a daily basis.

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

There are 6 operators available for flights from Florida Keys to Illinois as of May 2026.

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

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 Florida Keys to Illinois.

What documentation or ID do you need to fly to Illinois?

The required travel and health documents for your Illinois trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Illinois. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$59 Cheap Flights from Florida Keys to Illinois in 2026

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Find the cheapest flights from Florida Keys to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:30 am - 5:37 pm

MIA

STL

10h 07m

1 stop

6:33 pm - 1:53 pm

STL

MIA

18h 20m

1 stop

$124Frontier

Thu, Aug 6 - Sun, Aug 9

11:23 am - 5:33 pm

MIA

STL

7h 10m

1 stop

6:33 pm - 10:47 pm

STL

MIA

27h 14m

1 stop

$126Frontier

Thu, Jun 4 - Sun, Jun 7

10:59 am - 11:55 pm

EYW

ORD

13h 56m

1 stop

2:03 pm - 9:24 am

ORD

EYW

18h 21m

2 stops

$223Multiple Airlines

Thu, Oct 1 - Tue, Oct 6

7:53 pm - 6:47 pm

EYW

ORD

23h 54m

2 stops

4:49 pm - 10:19 am

ORD

EYW

16h 30m

1 stop

$278Multiple Airlines

Thu, Sep 3 - Thu, Sep 10

4:00 pm - 6:55 pm

EYW

ORD

3h 55mnonstop

10:55 am - 3:19 pm

ORD

EYW

3h 24mnonstop

$309United Airlines

Thu, Jul 23 - Sun, Jul 26

7:29 pm - 11:58 pm

EYW

ORD

5h 29m

1 stop

11:00 am - 3:25 pm

ORD

EYW

3h 25mnonstop

$319American Airlines

Thu, Jun 11 - Wed, Jun 17

7:29 pm - 11:58 pm

EYW

ORD

5h 29m

1 stop

6:29 am - 1:41 pm

ORD

EYW

6h 12m

1 stop

$329American Airlines

Thu, Jun 11 - Wed, Jun 17

6:18 pm - 10:15 pm

EYW

MDW

4h 57m

1 stop

6:00 am - 1:29 pm

MDW

EYW

6h 29m

1 stop

$329Delta

Thu, Jul 23 - Sun, Jul 26

4:05 pm - 10:21 pm

MIA

MLI

7h 16m

1 stop

5:56 am - 12:56 pm

MLI

MIA

6h 00m

1 stop

$338Delta

Wed, May 27 - Sat, May 30

12:00 pm - 5:51 pm

MIA

MLI

6h 51m

1 stop

2:26 pm - 10:17 pm

MLI

MIA

6h 51m

1 stop

$383United Airlines

Wed, Oct 28 - Sat, Oct 31

Delta flights from Florida Keys to Illinois

Our best Delta deals on Florida Keys to Illinois flight tickets

Delta

Jun 17

MIA1:38 pmMiami

7h 53m

1 stop

ORD8:31 pmChicago O'Hare Intl

Jun 24

ORD1:46 pmChicago O'Hare Intl

5h 10m

1 stop

MIA7:56 pmMiami

$219

Delta

May 24

MIA7:05 amMiami

4h 59m

1 stop

ORD11:04 amChicago O'Hare Intl

Jun 9

ORD5:30 amChicago O'Hare Intl

6h 34m

1 stop

MIA1:04 pmMiami

$278

Delta

Jul 23

EYW6:18 pmKey West

4h 57m

1 stop

MDW10:15 pmChicago Midway

Jul 26

MDW6:00 amChicago Midway

6h 29m

1 stop

EYW1:29 pmKey West

$329

Frontier flights from Florida Keys to Illinois

Our best Frontier deals on Florida Keys to Illinois flight tickets

Frontier

Aug 6

MIA8:30 amMiami

10h 07m

1 stop

STL5:37 pmLambert-St Louis

Aug 9

STL6:33 pmLambert-St Louis

18h 20m

1 stop

MIA1:53 pmMiami

$124

Frontier

Jun 4

MIA11:23 amMiami

7h 10m

1 stop

STL5:33 pmLambert-St Louis

Jun 7

STL6:33 pmLambert-St Louis

27h 14m

1 stop

MIA10:47 pmMiami

$126

Frontier

Jun 2

MIA8:10 amMiami

12h 19m

1 stop

ORD7:29 pmChicago O'Hare Intl

Jun 3

ORD6:55 amChicago O'Hare Intl

14h 52m

1 stop

MIA10:47 pmMiami

$134

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Thu 8/6

8:30 am-5:37 pm

1 stop10h 07m

Lambert-St Louis

Sun 8/9

6:33 pm-1:53 pm

1 stop18h 20m

$124

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Thu 6/4

11:23 am-5:33 pm

1 stop7h 10m

Lambert-St Louis

Sun 6/7

6:33 pm-10:47 pm

1 stop27h 14m

$126

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/1

10:59 am-11:55 pm

1 stop13h 56m

Chicago O'Hare Intl

Tue 10/6

2:03 pm-9:24 am

2 stops18h 21m

$223

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

7:53 pm-6:47 pm

2 stops23h 54m

Chicago O'Hare Intl

Thu 9/10

4:49 pm-10:19 am

1 stop16h 30m

$278

Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/23

4:00 pm-6:55 pm

Nonstop3h 55m

Chicago O'Hare Intl

Sun 7/26

10:55 am-3:19 pm

Nonstop3h 24m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 6/11

7:29 pm-11:58 pm

1 stop5h 29m

Chicago O'Hare Intl

Wed 6/17

11:00 am-3:25 pm

Nonstop3h 25m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 6/11

7:29 pm-11:58 pm

1 stop5h 29m

Chicago O'Hare Intl

Wed 6/17

6:29 am-1:41 pm

1 stop6h 12m

$329

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 7/23

6:18 pm-10:15 pm

1 stop4h 57m

Chicago Midway

Sun 7/26

6:00 am-1:29 pm

1 stop6h 29m

$329

MiamiMoline

MIA - MLI

MIAMLI

Miami

Wed 5/27

4:05 pm-10:21 pm

1 stop7h 16m

Moline Quad-City

Sat 5/30

5:56 am-12:56 pm

1 stop6h 00m

$338

MiamiMoline

MIA - MLI

MIAMLI

Miami

Wed 10/28

12:00 pm-5:51 pm

1 stop6h 51m

Moline Quad-City

Sat 10/31

2:26 pm-10:17 pm

1 stop6h 51m

$383

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 Florida Keys to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Florida Keys is in March. Flight prices, which tend to average around $27, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of March, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $40.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Florida Keys to Illinois is on a Wednesday when prices can be found for as low as $339. Flights from Florida Keys to Illinois on a Monday will generally be more expensive and average around $773. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the morning. Flights from Florida Keys to Illinois during this time can be as low as $427. Flights at noon are often more expensive with an average ticket price of $434.

What is the cheapest Florida Keys to Illinois flight route?

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

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

You are more likely to see cheaper flights to Illinois from Florida Keys when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $244 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Florida Keys for as low as $164 on momondo.

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

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

Cheap Florida Keys to Illinois flight deals and tips

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

Fastest flight time	2h 50m
Direct flights	Every day
Airports in Illinois	98 airports

The fastest flight from Florida Keys to Illinois takes 2h 50m

Direct flights go from Florida Keys to Illinois every day.

There are 98 airports in Illinois. From Florida Keys there are direct flights to Chicago Midway (MDW), Lambert-St Louis (STL).

Search flight deals

Frequently asked questions about flying from Florida Keys to Illinois

When did momondo last update prices for flights from Florida Keys to Illinois?
Prices for flights from Florida Keys to Illinois are refreshed on a daily basis.
How many operators does momondo search for flights from Florida Keys to Illinois?
There are 6 operators available for flights from Florida Keys to Illinois as of May 2026.
How old do you have to be to fly from Florida Keys to Illinois?
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 Florida Keys to Illinois.
What documentation or ID do you need to fly to Illinois?
The required travel and health documents for your Illinois trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Illinois. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Florida Keys to Illinois?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Florida Keys to Illinois is Boeing 737-800 (19.88% of total bookings). The next most popular plane models are Airbus A321neo (12.92%), Boeing 737-900 (8.72%), and Boeing 737 MAX 8 (8.34%).

Best airlines flying from Florida Keys to Illinois

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

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $344	Free Cancellation	Rating 7.1 11,654 reviews		Search American Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Illinois from Florida Keys.

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

Yes. All flights to Illinois from Florida Keys on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Florida Keys to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Florida Keys to Illinois right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Florida Keys to Illinois 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.