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Florida Keys

$54+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$112
(Kiwi.com)

One-way from

$54
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$201
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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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. 15% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 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 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Tue 5/139:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Wed 5/213:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Deal found 4/1$112
This Frontier deal was found by Cheapflights users on 4/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/86:00 amMDW - MIA
Nonstop3h 08mFrontier
Tue 4/1511:03 amMIA - MDW
Nonstop3h 28mFrontier
Deal found 4/2$133
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 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 4/3$148
This Southwest deal was found by Cheapflights users on 4/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/36:45 pmMDW - MIA
Nonstop2h 55mSouthwest
Wed 5/77:00 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 4/3$177
This American Airlines deal was found by Cheapflights users on 4/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/32:50 pmORD - MIA
Nonstop3h 09mAmerican Airlines
Wed 5/78:35 amMIA - ORD
Nonstop3h 34mAmerican Airlines
Deal found 4/3$178
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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.
Fri 5/165:21 pmORD - MIA
1 stop11h 01mFrontier
Mon 5/197:30 amMIA - ORD
1 stop11h 59mFrontier
Deal found 4/2$197
This American Airlines deal was found by Cheapflights users on 4/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/191:48 pmSTL - EYW
1 stop5h 23mAmerican Airlines
Wed 4/233:56 pmEYW - STL
1 stop7h 18mAmerican Airlines
Deal found 4/2$199
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/241:32 pmSTL - EYW
1 stop5h 08mDelta
Tue 7/16:29 pmEYW - STL
1 stop6h 13mDelta
Deal found 4/2$217
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2510:30 amORD - MIA
1 stop6h 37mDelta
Tue 5/277:30 pmMIA - ORD
1 stop5h 28mDelta
Deal found 4/2$217
This Delta deal was found by Cheapflights users on 4/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/175:25 pmMDW - MIA
1 stop5h 21mDelta
Tue 5/2010:37 amMIA - MDW
1 stop5h 43mDelta
Deal found 4/3$217
This CheapOair deal was found by Cheapflights users on 4/3. 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.
Fri 5/166:53 pmSTL - MIA
1 stop9h 29mFrontier
Tue 5/206:00 amMIA - STL
1 stop28h 59mFrontier
Deal found 4/3$230
This Southwest deal was found by Cheapflights users on 4/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/302:55 pmSTL - MIA
1 stop6h 00mSouthwest
Wed 5/77:55 amMIA - STL
Nonstop2h 55mSouthwest
Deal found 4/2$239

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 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

Tue 5/13

9:55 am-2:10 pm

Nonstop3h 15m

Miami

Wed 5/21

3:15 pm-5:41 pm

Nonstop3h 26m

$112

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 4/13

2:16 pm-6:22 pm

Nonstop3h 06m

Miami

Tue 4/15

11:03 am-1:31 pm

Nonstop3h 28m

$141

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

Sat 5/3

6:45 pm-10:40 pm

Nonstop2h 55m

Miami

Sat 5/10

5:05 am-7:15 am

Nonstop3h 10m

$177

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 5/3

2:50 pm-6:59 pm

Nonstop3h 09m

Miami

Tue 5/6

8:20 pm-10:48 pm

Nonstop3h 28m

$178

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 5/1

8:00 am-11:11 am

1 stop26h 11m

Miami

Sun 5/4

6:00 am-11:41 pm

1 stop18h 41m

$198

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Sat 4/19

1:48 pm-8:11 pm

1 stop5h 23m

Key West

Wed 4/23

3:56 pm-10:14 pm

1 stop7h 18m

$199

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 6/24

1:32 pm-7:40 pm

1 stop5h 08m

Key West

Tue 7/1

6:29 pm-11:42 pm

1 stop6h 13m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 5/25

10:30 am-6:07 pm

1 stop6h 37m

Miami

Tue 5/27

7:30 pm-11:58 pm

1 stop5h 28m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 5/17

5:25 pm-11:46 pm

1 stop5h 21m

Miami

Tue 5/20

10:37 am-3:20 pm

1 stop5h 43m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

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 3, 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 3, 2025.

The most flights from USIL to zzEOA are scheduled on a Monday (3 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (2 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 3, 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
9,825 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,825 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,274 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,619 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,920 reviews
Alaska Airlines
8.0
Very good
9,825 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $54. Frontier flights start at $63 while deals on Southwest start at $89 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$460FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$256Average$489FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$261Average$503FlexibilityNo cancel feeOn-time69%

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