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Florida Keys

$69+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
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 July 25, 2025.

Round-trip from

$133
(Cheapflightsfares)

One-way from

$69
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$229
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. 11% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 25, 2025.

This American Airlines deal was found by Cheapflights users on 7/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/52:50 pmORD - MIA
Nonstop3h 12mAmerican Airlines
Wed 11/59:57 pmMIA - ORD
Nonstop3h 24mAmerican Airlines
Deal found 7/21$132
This Cheapflightsfares deal was found by Cheapflights users on 7/22. 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.
Fri 9/268:56 pmORD - MIA
1 stop11h 05mSpirit Airlines
Wed 10/17:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 7/22$133
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/69:20 amMDW - MIA
Nonstop3h 00mSouthwest
Mon 9/812:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 7/24$137
This FlightHub deal was found by Cheapflights users on 7/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:23 pmMDW - MIA
1 stop26h 46mFrontier
Sun 10/266:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 7/23$154
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/67:30 amORD - MIA
1 stop8h 00mSouthwest
Mon 9/84:10 pmMIA - ORD
1 stop7h 55mSouthwest
Deal found 7/24$157
This CheapOair deal was found by Cheapflights users on 7/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/296:35 amORD - MIA
1 stop13h 10mMultiple Airlines
Mon 9/87:00 amMIA - ORD
Nonstop3h 18mMultiple Airlines
Deal found 7/23$174
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:55 pmSTL - MIA
Nonstop2h 45mSouthwest
Mon 9/87:35 amMIA - STL
1 stop7h 15mSouthwest
Deal found 7/22$178
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/275:26 amSTL - MIA
Nonstop2h 48mAmerican Airlines
Fri 8/2910:09 pmMIA - STL
Nonstop2h 50mAmerican Airlines
Deal found 7/22$184
This FlightHub deal was found by Cheapflights users on 7/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/242:30 pmSTL - MIA
1 stop17h 48mSpirit Airlines
Sat 8/303:15 pmMIA - STL
1 stop23h 17mSpirit Airlines
Deal found 7/22$189
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:01 amSTL - MIA
1 stop6h 27mDelta
Wed 9/247:30 amMIA - STL
1 stop5h 51mDelta
Deal found 7/24$197
This Delta deal was found by Cheapflights users on 7/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/61:08 pmMDW - MIA
1 stop7h 22mDelta
Sat 9/138:10 amMIA - MDW
1 stop5h 18mDelta
Deal found 7/24$217
This Frontier deal was found by Cheapflights users on 7/24. 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.
Wed 7/307:29 pmSTL - MIA
1 stop10h 01mFrontier
Sat 8/26:00 amMIA - STL
1 stop8h 59mFrontier
Deal found 7/24$218

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 July 25, 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

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/26

8:56 pm-9:01 am

1 stop11h 05m

Miami

Wed 10/1

7:00 am-9:18 am

Nonstop3h 18m

$133

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 9/4

8:05 am-12:13 pm

Nonstop3h 08m

Miami

Sun 9/7

6:20 am-8:40 am

Nonstop3h 20m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 9/6

9:20 am-1:20 pm

Nonstop3h 00m

Miami

Mon 9/8

12:35 pm-2:45 pm

Nonstop3h 10m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 10/17

7:23 pm-11:09 pm

1 stop26h 46m

Miami

Sun 10/19

6:53 pm-9:08 pm

Nonstop3h 15m

$154

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/6

7:30 am-4:30 pm

1 stop8h 00m

Miami

Mon 9/8

4:10 pm-11:05 pm

1 stop7h 55m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 8/29

6:35 am-8:45 pm

1 stop13h 10m

Miami

Mon 9/8

7:00 am-9:18 am

Nonstop3h 18m

$174

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Sat 9/6

5:55 pm-9:40 pm

Nonstop2h 45m

Miami

Mon 9/8

7:35 am-1:50 pm

1 stop7h 15m

$178

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Wed 8/27

5:26 am-9:14 am

Nonstop2h 48m

Miami

Fri 8/29

10:09 pm-11:59 pm

Nonstop2h 50m

$184

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Sun 8/24

2:30 pm-9:18 am

1 stop17h 48m

Miami

Sat 8/30

3:15 pm-1:32 pm

1 stop23h 17m

$189

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Wed 9/17

6:01 am-1:28 pm

1 stop6h 27m

Miami

Wed 9/24

7:30 am-12:21 pm

1 stop5h 51m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

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 $492). 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 July 25, 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.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated July 25, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Illinois to Florida Keys. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,967 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,880 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Spirit Airlines
6.3
Okay
8,034 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $69. Southwest flights start at $69 while deals on American Airlines start at $70 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 $492). 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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$486FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$527FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$488FlexibilityNo cancel feeOn-time71%

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