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Florida Keys

$62+ Cheap flights from Illinois to Florida Keys

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheap flight deals from Illinois to Florida Keys

Keep the following information in mind while searching for Illinois to Florida Keys flight deals. Data was last updated September 19, 2025.

Round-trip from

$104
(Kiwi.com)

One-way from

$62
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$231
From Illinois to Florida Keys
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One-way flight from Illinois to Florida Keys
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Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Illinois to Florida Keys

Cheapest flights from Illinois to Florida Keys
Explore the most affordable flight options available from Illinois to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2211:00 amORD - MIA
1 stop6h 45mFrontier
Tue 10/283:06 pmMIA - ORD
1 stop21h 08mFrontier
Deal found 9/18$104
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:33 amMDW - MIA
Nonstop3h 00mFrontier
Fri 10/249:00 amMIA - MDW
Nonstop3h 17mFrontier
Deal found 9/18$105
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/141:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Sun 11/1610:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Deal found 9/18$105
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/119:27 amORD - MIA
Nonstop3h 03mSpirit Airlines
Sun 10/127:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/17$107
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:33 amMDW - MIA
Nonstop3h 00mFrontier
Sat 11/17:05 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 9/18$108
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/610:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sat 10/186:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/17$108
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1710:33 amMDW - MIA
Nonstop3h 00mFrontier
Sat 11/87:05 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 9/17$109
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sun 10/267:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 9/17$109
This Frontier deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:05 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 11/37:25 amMIA - MDW
1 stop11h 24mFrontier
Deal found 9/17$110
This Priceline deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/111:14 pmORD - MIA
1 stop9h 29mMultiple Airlines
Thu 10/167:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Deal found 9/17$111
This Orbitz deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2510:00 amMDW - MIA
1 stop12h 43mFrontier
Sat 11/17:05 pmMIA - MDW
Nonstop3h 17mFrontier
Deal found 9/18$112
This Cheapflightsfares deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1210:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Sat 10/186:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 9/18$112

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Florida Keys that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 19, 2025.
Use the filters below to find and compare flights from Illinois to Florida Keys that are best for you.

Fly from

Illinois

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/30

1:37 pm-12:34 am

1 stop9h 57m

Miami

Sun 11/2

5:00 am-10:30 am

1 stop30h 30m

$143

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 10/24

12:11 pm-6:19 am

1 stop17h 08m

Miami

Sun 10/26

6:00 am-11:16 am

1 stop30h 16m

$144

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 11/10

9:30 am-1:35 pm

Nonstop3h 05m

Miami

Fri 11/14

6:20 am-8:35 am

Nonstop3h 15m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 10/27

10:35 am-2:50 pm

Nonstop3h 15m

Miami

Wed 10/29

7:00 am-9:29 am

Nonstop3h 29m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 10/27

8:10 am-12:10 pm

Nonstop3h 00m

Miami

Wed 10/29

6:55 am-12:10 pm

2 stops6h 15m

$192

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Sat 11/8

5:15 pm-12:29 am

1 stop6h 14m

Miami

Sat 11/15

6:00 am-10:23 am

1 stop5h 23m

$197

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Sat 11/1

5:15 pm-12:29 am

1 stop6h 14m

Miami

Tue 11/4

6:00 am-12:35 pm

1 stop7h 35m

$197

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Mon 1/19

10:00 am-3:47 pm

1 stop4h 47m

Miami

Fri 1/23

4:40 pm-8:39 pm

1 stop4h 59m

$199

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Fri 10/24

1:55 pm-10:35 pm

1 stop7h 40m

Miami

Sat 11/1

5:45 am-7:35 am

Nonstop2h 50m

$214

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 10/21

12:48 pm-6:34 pm

1 stop4h 46m

Miami

Tue 10/28

8:30 am-12:28 pm

1 stop4h 58m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Florida Keys

What is the cheapest month to book a flight from Illinois to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Illinois to Florida Keys (average of $328). Flying from Illinois to Florida Keys in March is currently the most expensive (average of $491). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to EOA?

Find hourly flight availability from Illinois to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 19, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Florida Keys as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Florida Keys?

    Airlines like Frontier, Southwest, and United Airlines fly from Illinois to Florida Keys in about 3h 05m. The time it takes to get you to your destination can typically vary by up to 6h 52m. Airlines will cover a distance of 1183 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Illinois to Florida Keys one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $72. Southwest flights start at $79 while deals on United Airlines start at $79 one-way.

  • Can I find deals for flights from Illinois to Florida Keys that include hotel bookings?

    Yes. In addition to deals on Illinois to Florida Keys flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Florida Keys?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Florida Keys.

  • Can I find deals for business class flights from Illinois to Florida Keys?

    Yes. Cheapflights offers flight deals from Illinois to Florida Keys by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Illinois to Florida Keys (average of $328). Flying from Illinois to Florida Keys in March is currently the most expensive (average of $491). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Illinois to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Illinois to Florida Keys

Discover the top 3 airlines that operate flights from Illinois to Florida Keys. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$498FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$530FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$463FlexibilityNo cancel feeOn-time71%

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