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Florida Keys

$68+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$131
(Booking.com)

One-way from

$68
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$272
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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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. 14% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/115:51 amORD - MIA
1 stop6h 15mSpirit Airlines
Tue 6/177:20 pmMIA - ORD
Nonstop3h 36mSpirit Airlines
Deal found 4/23$131
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/79:55 amORD - MIA
Nonstop3h 15mMultiple Airlines
Sun 5/117:12 amMIA - ORD
1 stop9h 45mMultiple Airlines
Deal found 4/23$148
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/19:45 amMDW - MIA
Nonstop3h 05mSouthwest
Sat 7/55:45 amMIA - MDW
Nonstop3h 05mSouthwest
Deal found 4/23$179
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:50 pmORD - MIA
Nonstop3h 08mAmerican Airlines
Tue 5/278:20 pmMIA - ORD
Nonstop3h 28mAmerican Airlines
Deal found 4/23$187
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/292:58 pmORD - MIA
1 stop7h 45mFrontier
Sun 6/110:59 pmMIA - ORD
1 stop12h 38mFrontier
Deal found 4/23$198
This JetBlue deal was found by Cheapflights users on 4/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/114:03 pmORD - MIA
1 stop7h 10mJetBlue
Mon 6/166:00 amMIA - ORD
1 stop10h 53mJetBlue
Deal found 4/23$217
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/119:24 amMDW - MIA
1 stop6h 46mDelta
Wed 6/188:11 amMIA - MDW
1 stop5h 18mDelta
Deal found 4/23$217
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/28:30 amMDW - MIA
1 stop22h 58mFrontier
Wed 5/78:37 pmMIA - MDW
1 stop17h 57mFrontier
Deal found 4/23$221
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/215:13 amSTL - EYW
1 stop6h 38mAmerican Airlines
Wed 5/2812:50 pmEYW - STL
1 stop7h 33mAmerican Airlines
Deal found 4/23$225
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Sat 5/247:55 pmSTL - MIA
1 stop9h 35mFrontier
Sun 6/16:00 amMIA - STL
1 stop28h 12mFrontier
Deal found 4/23$231
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/315:55 amMLI - EYW
1 stop6h 14mDelta
Sat 9/611:45 amEYW - MLI
1 stop5h 37mDelta
Deal found 4/22$234
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Sun 8/317:19 amMLI - EYW
1 stop5h 14mAmerican Airlines
Sat 9/64:01 pmEYW - MLI
2 stops8h 21mAmerican Airlines
Deal found 4/22$235

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 April 24, 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

Wed 6/11

5:51 am-1:06 pm

1 stop6h 15m

Miami

Tue 6/17

7:20 pm-9:56 pm

Nonstop3h 36m

$131

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/7

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Sun 5/11

7:12 am-3:57 pm

1 stop9h 45m

$148

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 7/1

9:45 am-1:50 pm

Nonstop3h 05m

Miami

Sat 7/5

5:45 am-7:50 am

Nonstop3h 05m

$179

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/24

4:50 pm-8:58 pm

Nonstop3h 08m

Miami

Tue 5/27

8:20 pm-10:48 pm

Nonstop3h 28m

$187

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/29

2:58 pm-11:43 pm

1 stop7h 45m

Miami

Sun 6/1

10:59 pm-10:37 am

1 stop12h 38m

$198

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 6/11

9:49 am-6:17 pm

1 stop7h 28m

Miami

Sat 6/14

5:30 am-12:29 pm

1 stop7h 59m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 6/11

9:24 am-5:10 pm

1 stop6h 46m

Miami

Wed 6/18

8:11 am-12:29 pm

1 stop5h 18m

$217

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 5/21

5:13 am-12:51 pm

1 stop6h 38m

Key West

Wed 5/28

12:50 pm-7:23 pm

1 stop7h 33m

$225

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 5/12

6:15 am-11:31 pm

1 stop16h 16m

Miami

Thu 5/15

8:46 am-1:34 pm

1 stop5h 48m

$225

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Sat 5/31

7:55 pm-6:30 am

1 stop9h 35m

Miami

Fri 6/6

6:00 am-10:08 am

1 stop29h 08m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 $493). 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 April 24, 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.

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 April 24, 2025.

The most flights from USIL to zzEOA are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

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 April 24, 2025.
To help decide which airline to fly from Illinois to Florida Keys, see what other customers have to say about Alaska Airlines, Southwest and Delta. 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.
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 Spirit Airlines, which is currently one of the cheapest options available, starting at $68. Frontier flights start at $79 while deals on American Airlines start at $90 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 $493). 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$469FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$260Average$491FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$262Average$503FlexibilityNo cancel feeOn-time69%

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