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Florida Keys

$45+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Feb 28 — Mrz 71
Fr 2/28
Fr 3/7
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 Februar 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Cheapflightsfares)

One-way from

$45
(FlightHub)

Popular in

December

Cheapest in

July

Average price

$263
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. 16% potential increase in price ($48 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 February 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 Februar 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/59:01 pmORD - MIA
1 stop11h 29mSpirit Airlines
Di 4/85:52 amMIA - ORD
Nonstop3h 37mSpirit Airlines
Deal found 2/22$97
This Frontier deal was found by Cheapflights users on 2/21. 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.
So 4/62:16 pmMDW - MIA
Nonstop3h 06mFrontier
Di 4/811:03 amMIA - MDW
Nonstop3h 28mFrontier
Deal found 2/21$98
This Cheapflightsfares deal was found by Cheapflights users on 2/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/106:30 amORD - MIA
1 stop16h 38mFrontier
Mi 4/166:25 amMIA - ORD
1 stop19h 12mFrontier
Deal found 2/23$103
This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 3/254:32 pmORD - MIA
Nonstop3h 13mMultiple Airlines
Mi 4/26:25 amMIA - ORD
1 stop19h 17mMultiple Airlines
Deal found 2/22$105
This Southwest deal was found by Cheapflights users on 2/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/57:50 pmMDW - MIA
Nonstop2h 55mSouthwest
Mi 4/97:00 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 2/22$179
This Delta deal was found by Cheapflights users on 2/22. 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.
Mi 4/167:05 amORD - MIA
1 stop5h 45mDelta
Sa 4/266:00 amMIA - ORD
1 stop5h 03mDelta
Deal found 2/22$217
This Delta deal was found by Cheapflights users on 2/23. 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.
Mi 4/99:23 amMDW - MIA
1 stop5h 59mDelta
Mi 4/1612:38 pmMIA - MDW
1 stop6h 42mDelta
Deal found 2/23$217
This Delta deal was found by Cheapflights users on 2/22. 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.
Di 6/310:10 amSTL - EYW
1 stop6h 02mDelta
Mi 6/117:00 amEYW - STL
1 stop6h 24mDelta
Deal found 2/22$259
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/86:47 pmSTL - MIA
3 stops29h 19mMultiple Airlines
Di 4/159:55 pmMIA - STL
3 stops47h 15mMultiple Airlines
Deal found 2/22$267
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 4/276:11 pmSTL - MIA
2 stops27h 11mSpirit Airlines
Mi 4/3010:34 amMIA - STL
3 stops31h 42mSpirit Airlines
Deal found 2/22$274
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Mi 3/125:01 amSTL - MIA
Nonstop2h 53mAmerican Airlines
Mi 3/199:50 pmMIA - STL
Nonstop3h 06mAmerican Airlines
Deal found 2/22$277
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Mi 4/97:35 amSTL - EYW
2 stops8h 54mAmerican Airlines
Di 4/151:39 pmEYW - STL
2 stops6h 44mAmerican Airlines
Deal found 2/21$279

Find flights from Illinois to Florida Keys within your budget

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 Februar 23, 2025.

Fly from

Illinois

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sa 4/5

9:01 pm-9:30 am

1 stop11h 29m

Miami

Di 4/8

5:52 am-8:29 am

Nonstop3h 37m

$97

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

So 4/6

2:16 pm-6:22 pm

Nonstop3h 06m

Miami

Di 4/8

11:03 am-1:31 pm

Nonstop3h 28m

$98

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Do 4/10

6:30 am-12:08 am

1 stop16h 38m

Miami

Mi 4/16

6:25 am-12:37 am

1 stop19h 12m

$103

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mo 3/10

2:34 pm-6:47 pm

Nonstop3h 13m

Miami

Mi 3/12

6:30 am-5:26 pm

1 stop11h 56m

$110

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sa 4/5

7:50 pm-11:45 pm

Nonstop2h 55m

Miami

Mi 4/9

7:00 am-9:10 am

Nonstop3h 10m

$179

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mi 4/16

7:05 am-3:38 pm

1 stop7h 33m

Miami

Mi 4/23

6:00 am-10:03 am

1 stop5h 03m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mi 4/9

2:57 pm-9:18 pm

1 stop5h 21m

Miami

Mi 4/16

6:00 am-12:03 pm

1 stop7h 03m

$217

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Di 6/3

10:10 am-5:12 pm

1 stop6h 02m

Key West

Mi 6/11

7:00 am-12:24 pm

1 stop6h 24m

$259

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

Di 4/8

6:47 pm-1:06 am

3 stops29h 19m

Miami

Di 4/15

9:55 pm-8:10 pm

3 stops47h 15m

$267

St. LouisMiami

STL - MIA

STLMIA

Lambert-St Louis

So 4/27

6:11 pm-10:22 pm

2 stops27h 11m

Miami

Mi 4/30

10:34 am-5:16 pm

3 stops31h 42m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Illinois to Florida Keys

Get recent, data-driven insights about flights from Illinois to Florida Keys including ideal travel times, pricing trends, and more.

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 $510). 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 Februar 23, 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 Februar 23, 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 Februar 23, 2025.
To help decide which airline to fly from Illinois to Florida Keys, see what other customers have to say about Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,387 reviews

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,387 reviews
Southwest
8.1
Very good
4,387 reviews

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,707 reviews
Southwest
8.1
Very good
4,387 reviews

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,191 reviews
Southwest
8.1
Very good
4,387 reviews

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,746 reviews
Southwest
8.1
Very good
4,387 reviews

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
762 reviews
Southwest
8.1
Very good
4,387 reviews

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $45. Frontier flights start at $49 while deals on Southwest 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 $510). 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 Februar 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$483FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$247Average$485FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$469FlexibilityNo cancel feeOn-time69%
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