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Florida Keys

$53+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Super.com deal was found by Cheapflights users on 12/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Wed 1/710:13 amMIA - ORD
1 stop6h 47mSpirit Airlines
Deal found 12/17$102
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Fri 1/93:48 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 12/16$106
This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mFrontier
Wed 1/75:07 pmMIA - MDW
1 stop6h 10mFrontier
Deal found 12/15$108
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Sat 1/105:54 amMIA - ORD
Nonstop3h 24mSpirit Airlines
Deal found 12/16$119
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/316:05 amORD - MIA
1 stop12h 25mMultiple Airlines
Fri 1/95:54 amMIA - ORD
Nonstop3h 24mMultiple Airlines
Deal found 12/17$138
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/316:05 amORD - MIA
1 stop12h 25mMultiple Airlines
Wed 1/710:13 amMIA - ORD
1 stop6h 47mMultiple Airlines
Deal found 12/17$147
This Mytrip deal was found by Cheapflights users on 12/15. 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.
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Tue 1/69:59 pmMIA - ORD
2 stops23h 05mSpirit Airlines
Deal found 12/15$162
This Priceline deal was found by Cheapflights users on 12/15. 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.
Tue 12/167:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Sat 1/105:54 amMIA - ORD
Nonstop3h 24mSpirit Airlines
Deal found 12/15$163
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/306:50 amORD - MIA
1 stop14h 09mMultiple Airlines
Wed 1/215:54 amMIA - ORD
Nonstop3h 24mMultiple Airlines
Deal found 12/17$168
This CheapOair deal was found by Cheapflights users on 12/16. 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.
Wed 12/246:12 amMDW - MIA
1 stop12h 18mFrontier
Fri 1/911:43 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 12/16$192
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mMultiple Airlines
Tue 1/68:00 amMIA - MDW
1 stop15h 17mMultiple Airlines
Deal found 12/17$199
This CheapOair deal was found by Cheapflights users on 12/16. 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.
Tue 12/306:14 amMDW - MIA
1 stop12h 16mFrontier
Wed 1/711:43 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 12/16$203

Find 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 December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$99
(CheapOair)

One-way from

$53
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$346
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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From Illinois to Florida Keys
Search Deals
One-way flight from Illinois to Florida Keys
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Mon 5/4

6:34 pm-10:51 pm

Nonstop3h 17m

Miami

Thu 5/7

3:47 pm-6:15 pm

Nonstop3h 28m

$108

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/6

6:34 pm-10:51 pm

Nonstop3h 17m

Miami

Sun 5/10

7:35 am-6:40 pm

1 stop12h 05m

$196

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 1/14

11:39 am-5:46 pm

1 stop5h 07m

Miami

Sun 1/18

4:44 pm-7:09 pm

Nonstop3h 25m

$202

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 1/28

8:22 pm-11:56 am

2 stops14h 34m

Key West

Thu 2/5

9:46 am-10:23 am

1 stop25h 37m

$208

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 2/17

12:45 pm-9:59 pm

1 stop8h 14m

Miami

Tue 2/24

9:00 am-11:38 am

Nonstop3h 38m

$209

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 4/16

7:41 am-3:04 pm

1 stop6h 23m

Miami

Thu 4/23

7:35 am-6:40 pm

1 stop12h 05m

$209

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 1/20

10:35 am-5:45 pm

1 stop6h 10m

Miami

Tue 1/27

12:00 pm-4:55 pm

1 stop5h 55m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/7

6:03 pm-12:51 am

1 stop5h 48m

Miami

Thu 2/19

6:00 am-10:08 am

1 stop5h 08m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/15

4:13 pm-12:53 am

1 stop7h 40m

Miami

Fri 2/20

6:00 am-9:56 am

1 stop4h 56m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/31

4:30 pm-12:51 am

1 stop7h 21m

Miami

Sat 2/7

8:05 am-12:46 pm

1 stop5h 41m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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, November is the cheapest month in which you can book a flight from Illinois to Florida Keys (average of $200). Flying from Illinois to Florida Keys in June is currently the most expensive (average of $300). 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 December 18, 2025.

When flying from Illinois to Florida Keys, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 32% versus a flight in the evening.

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 Spirit Airlines, Frontier, and United Airlines fly from Illinois to Florida Keys in about 3h 17m. The time it takes to get you to your destination can typically vary by up to 4h 57m. Airlines will cover a distance of 1198 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 $38. Spirit Airlines flights start at $42 while deals on American Airlines start at $71 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, November is the cheapest month in which you can book a flight from Illinois to Florida Keys (average of $200). Flying from Illinois to Florida Keys in June is currently the most expensive (average of $300). 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 4 airlines flying from Illinois to Florida Keys

Discover the top 4 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$199Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$486FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$562FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$453FlexibilityNo cancel feeOn-time71%

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