HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$55+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to Florida Keys with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$108
(Priceline)

One-way from

$55
(Priceline)

Popular in

March

Cheapest in

September

Average price

$292
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. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 3, 2025.

This CheapOair deal was found by Cheapflights users on 11/1. 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 11/295:57 pmMDW - MIA
Nonstop3h 06mFrontier
Sat 12/68:09 pmMIA - MDW
Nonstop3h 21mFrontier
Deal found 11/1$108
This Frontier deal was found by Cheapflights users on 11/3. 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 11/265:57 pmMDW - MIA
Nonstop3h 06mFrontier
Sat 12/69:38 amMIA - MDW
1 stop5h 21mFrontier
Deal found 11/3$109
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/211:40 amORD - MIA
Nonstop3h 07mMultiple Airlines
Tue 12/95:58 pmMIA - ORD
1 stop21h 33mMultiple Airlines
Deal found 11/2$109
This Frontier deal was found by Cheapflights users on 11/3. 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.
Thu 12/42:16 pmMDW - MIA
Nonstop3h 10mFrontier
Sun 12/78:09 pmMIA - MDW
Nonstop3h 21mFrontier
Deal found 11/3$110
This CheapOair deal was found by Cheapflights users on 11/3. 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.
Thu 12/49:21 amORD - MIA
1 stop12h 57mFrontier
Sat 12/132:13 pmMIA - ORD
1 stop21h 18mFrontier
Deal found 11/3$110
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/32:01 pmORD - MIA
1 stop6h 30mSpirit Airlines
Fri 12/54:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 11/1$111
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/265:57 pmMDW - MIA
Nonstop3h 06mFrontier
Tue 12/25:58 pmMIA - MDW
1 stop15h 48mFrontier
Deal found 11/1$112
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/177:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Fri 12/262:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 11/2$112
This CheapOair deal was found by Cheapflights users on 11/1. 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.
Mon 12/1512:35 pmMDW - MIA
1 stop9h 43mFrontier
Mon 12/2211:42 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 11/1$114
This Frontier deal was found by Cheapflights users on 11/1. 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 12/72:59 pmMDW - MIA
Nonstop3h 10mFrontier
Mon 12/85:30 amMIA - MDW
1 stop5h 22mFrontier
Deal found 11/1$115
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/3011:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Sat 12/64:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 11/2$115
This CheapOair deal was found by Cheapflights users on 11/2. 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 11/152:05 pmMDW - MIA
Nonstop3h 00mFrontier
Sun 11/166:00 amMIA - MDW
1 stop30h 30mFrontier
Deal found 11/2$116

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 November 3, 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

Thu 12/4

12:39 pm-4:50 pm

Nonstop3h 11m

Miami

Thu 12/11

12:23 pm-2:52 pm

Nonstop3h 29m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/24

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 1/31

6:30 am-8:40 am

Nonstop3h 10m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 12/9

9:20 am-4:10 pm

1 stop5h 50m

Miami

Wed 12/10

1:05 pm-3:20 pm

Nonstop3h 15m

$187

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 12/3

5:30 am-11:21 am

1 stop4h 51m

Miami

Wed 12/10

10:32 am-3:20 pm

1 stop5h 48m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 12/5

5:59 pm-12:46 am

1 stop5h 47m

Miami

Wed 12/10

12:36 pm-4:48 pm

1 stop5h 12m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 12/6

1:14 pm-9:50 pm

1 stop7h 36m

Miami

Sun 12/14

7:00 am-11:55 am

1 stop5h 55m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/1

6:00 am-12:14 pm

1 stop5h 14m

Miami

Fri 2/6

7:15 am-12:01 pm

1 stop5h 46m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 12/3

6:00 am-1:06 pm

1 stop6h 06m

Miami

Thu 12/11

8:05 am-11:55 am

1 stop4h 50m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 12/3

12:50 pm-6:26 pm

1 stop4h 36m

Miami

Tue 12/9

6:00 am-9:54 am

1 stop4h 54m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 12/11

5:13 pm-12:46 am

1 stop6h 33m

Miami

Sun 12/14

7:00 am-11:55 am

1 stop5h 55m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 results
1
2
3
...
6

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 November 3, 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 31% versus a flight in the evening.

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 November 3, 2025.

The most flights from USIL to zzEOA are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, 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, Southwest, and Delta 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 1h 51m. 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 $61. United Airlines flights start at $79 while deals on American 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, 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Fort Lauderdale flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
John F Kennedy Intl to Orlando flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
Newark to Orlando flights
John F Kennedy Intl to West Palm Beach flights
Newark to West Palm Beach flights
Dulles Intl to Miami flights
John F Kennedy Intl to Tampa flights
Philadelphia to Orlando flights
LaGuardia to Orlando flights
Dallas/Fort Worth to Orlando flights
Boston to Fort Lauderdale flights
Boston to Miami flights
Newark to Tampa flights
LaGuardia to West Palm Beach flights
Boston to Orlando flights
Baltimore to Fort Lauderdale flights
LaGuardia to Tampa flights
Boston to Tampa flights
O'Hare Intl to Orlando flights
Los Angeles to Miami flights
Reagan-National to Miami flights
O'Hare Intl to Miami flights
Los Angeles to Orlando flights
Reagan-National to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Dulles Intl to Orlando flights
Denver to Orlando flights
Los Angeles to Fort Lauderdale flights
Philadelphia to Fort Lauderdale flights
Minneapolis to Orlando flights
Detroit to Fort Lauderdale flights
John F Kennedy Intl to Fort Myers flights
Cleveland to Orlando flights
Detroit to Orlando flights
Providence to Orlando flights
Minneapolis to Miami flights
Newark to Fort Myers flights
Dulles Intl to Fort Lauderdale flights
Seattle to Orlando flights
Philadelphia to Miami flights
Boston to West Palm Beach flights
Baltimore to Orlando flights
Dallas/Fort Worth to Miami flights
Boston to Fort Myers flights

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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$531FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$533FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$471FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.