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Florida Keys

$42+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Frontier deal was found by Cheapflights users on 1/27. 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.
Sun 2/156:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Thu 2/1911:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/27$85
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 3/17:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Fri 3/67:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 1/26$85
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2811:48 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Thu 3/53:50 pm
MIA
-
ORD
Nonstop3h 28m
Multiple Airlines
Deal found 1/27$86
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 2/2811:48 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Wed 3/47:12 am
MIA
-
ORD
Nonstop3h 27m
Multiple Airlines
Deal found 1/27$87
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 2/1411:48 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Thu 2/197:12 am
MIA
-
ORD
Nonstop3h 27m
Multiple Airlines
Deal found 1/28$88
This CheapOair deal was found by Cheapflights users on 1/28. 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 2/39:23 am
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Fri 3/63:50 pm
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 1/28$89
This Priceline deal was found by Cheapflights users on 1/27. 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 2/249:18 am
ORD
-
MIA
1 stop10h 33m
Multiple Airlines
Sat 2/288:00 am
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 1/27$90
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/86:57 pm
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Tue 2/105:54 am
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 1/28$91
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Sat 2/218:59 am
ORD
-
MIA
1 stop10h 52m
Spirit Airlines
Sat 2/287:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 1/28$92
This CheapOair deal was found by Cheapflights users on 1/27. 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 2/179:18 am
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Sat 2/219:53 pm
MIA
-
ORD
1 stop11h 01m
Spirit Airlines
Deal found 1/27$93
This Frontier deal was found by Cheapflights users on 1/27. 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 3/76:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Mon 3/1611:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/27$94
This Priceline deal was found by Cheapflights users on 1/27. 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.
Wed 2/257:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Thu 3/196:00 am
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 1/27$94

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$85
(Frontier)

One-way from

$42
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$237
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
Search Deals
From Illinois to Florida Keys
Search Deals
One-way flight from Illinois to Florida Keys
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Wed 3/4

10:35 am-2:58 pm

Nonstop3h 23m

Miami

Fri 3/6

4:10 pm-6:55 pm

Nonstop3h 45m

$177

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 2/7

5:42 pm-9:06 am

1 stop14h 24m

Key West

Thu 2/12

9:46 am-11:59 pm

1 stop15h 13m

$199

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/18

1:57 pm-9:18 pm

1 stop6h 21m

Miami

Wed 3/25

4:44 pm-9:10 pm

1 stop5h 26m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 2/25

9:52 am-3:41 pm

1 stop4h 49m

Miami

Tue 3/3

12:00 pm-4:51 pm

1 stop5h 51m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 2/28

4:13 pm-12:53 am

1 stop7h 40m

Miami

Wed 3/4

8:05 am-12:46 pm

1 stop5h 41m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 2/26

6:40 pm-12:53 am

1 stop5h 13m

Miami

Tue 3/3

12:00 pm-5:45 pm

1 stop6h 45m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 3/7

4:13 pm-12:53 am

1 stop7h 40m

Miami

Wed 3/11

8:00 am-12:29 pm

1 stop5h 29m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 3/23

1:10 pm-9:18 pm

1 stop7h 08m

Miami

Thu 3/26

8:00 am-12:29 pm

1 stop5h 29m

$219

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 4/18

11:43 am-7:40 pm

1 stop6h 57m

Key West

Wed 4/22

6:19 pm-11:34 pm

1 stop6h 15m

$223

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 2/25

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 2/28

6:00 am-3:45 pm

1 stop10h 45m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 $308). 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 January 29, 2026.

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.

Weekly flight availability from Illinois to Florida Keys

Explore weekly flight availability from Illinois to Florida Keys. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 29, 2026.

The most flights from USIL to zzEOA are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).

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 United Airlines, Delta, and Southwest fly from Illinois to Florida Keys in about 3h. The time it takes to get you to your destination can typically vary by up to 3h 21m. 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 $37. Spirit Airlines flights start at $38 while deals on JetBlue start at $68 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 $308). 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

Browse thousands of different options on Cheapflights for your next trip

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$145Average$385FlexibilityNo cancel feeOn-time65%
DeltaCheapest$248Average$498FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$249Average$515FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$449FlexibilityNo cancel feeOn-time71%

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