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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — EYW
Jan 26 — Feb 21
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Cheap flight deals from Illinois to Florida Keys

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Florida Keys (zzEOA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$105
(Trip.com)

One-way from

$54
(Trip.com)
From Illinois to Florida Keys
One-way flight from Illinois to Florida Keys

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 January 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/197:25 amMDW - MIA
Nonstop3h 12mFrontier
Sat 2/226:25 amMIA - MDW
1 stop18h 52mFrontier
Deal found 1/20$107
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/198:33 amORD - MIA
1 stop8h 17mMultiple Airlines
Sat 2/228:05 amMIA - ORD
Nonstop3h 32mMultiple Airlines
Deal found 1/21$107
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/227:25 amORD - MIA
1 stop14h 55mFrontier
Thu 2/271:29 pmMIA - ORD
1 stop8h 22mFrontier
Deal found 1/21$108
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 2/22:02 pmORD - MIA
Nonstop3h 14mSpirit Airlines
Tue 2/410:00 amMIA - ORD
Nonstop3h 29mSpirit Airlines
Deal found 1/20$109
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Sun 2/231:59 pmORD - MIA
Nonstop3h 11mAmerican Airlines
Tue 2/258:27 amMIA - ORD
Nonstop3h 30mAmerican Airlines
Deal found 1/21$157
This United Airlines deal was found by Cheapflights users on 1/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/182:06 pmORD - MIA
Nonstop3h 20mUnited Airlines
Tue 2/257:00 amMIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 1/21$177
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/182:08 pmMDW - MIA
1 stop6h 34mDelta
Thu 2/206:00 amMIA - MDW
1 stop5h 12mDelta
Deal found 1/21$217
This Southwest deal was found by Cheapflights users on 1/20. 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.
Mon 2/36:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Wed 2/54:40 pmMIA - MDW
Nonstop3h 15mSouthwest
Deal found 1/20$237
This Delta deal was found by Cheapflights users on 1/20. 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 2/85:10 pmORD - MIA
1 stop6h 41mDelta
Wed 2/121:34 pmMIA - ORD
1 stop4h 51mDelta
Deal found 1/20$237
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/1811:31 amMLI - MIA
1 stop6h 31mAmerican Airlines
Tue 2/258:21 amMIA - MLI
1 stop7h 29mAmerican Airlines
Deal found 1/21$239
This JetBlue deal was found by Cheapflights users on 1/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/311:24 pmORD - MIA
1 stop9h 27mJetBlue
Tue 4/87:00 amMIA - ORD
1 stop6h 27mJetBlue
Deal found 1/21$255
This Delta deal was found by Cheapflights users on 1/20. 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 7/11:30 pmSTL - EYW
1 stop5h 16mDelta
Thu 7/107:00 amEYW - STL
1 stop6h 24mDelta
Deal found 1/20$259

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 2/10

2:02 pm-6:16 pm

Nonstop3h 14m

Miami

Tue 2/25

9:42 pm-7:28 am

1 stop10h 46m

$105

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/18

7:25 am-11:37 am

Nonstop3h 12m

Miami

Tue 2/25

9:42 pm-7:07 am

1 stop10h 25m

$105

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 5/7

7:00 am-11:14 am

Nonstop3h 14m

Miami

Sat 5/10

7:21 pm-9:30 pm

Nonstop3h 09m

$106

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/22

7:25 am-11:20 pm

1 stop14h 55m

Miami

Tue 2/25

9:42 pm-7:28 am

1 stop10h 46m

$108

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 2/23

7:00 am-11:10 am

Nonstop3h 10m

Miami

Wed 2/26

9:12 am-11:40 am

Nonstop3h 28m

$157

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 4/2

10:37 am-6:44 pm

1 stop7h 07m

Miami

Tue 4/8

7:00 am-12:27 pm

1 stop6h 27m

$197

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/18

2:08 pm-9:42 pm

1 stop6h 34m

Miami

Thu 2/27

6:00 am-11:59 am

1 stop6h 59m

$217

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 2/8

5:10 pm-12:51 am

1 stop6h 41m

Miami

Wed 2/12

1:34 pm-5:25 pm

1 stop4h 51m

$237

MolineMiami

MLI - MIA

MLIMIA

Moline Quad-City

Tue 2/18

11:31 am-7:02 pm

1 stop6h 31m

Miami

Tue 2/25

8:21 am-2:50 pm

1 stop7h 29m

$239

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/31

12:45 pm-5:06 pm

Nonstop3h 21m

Miami

Tue 2/25

7:00 am-9:34 am

Nonstop3h 34m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 $531). 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 21, 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 January 21, 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).

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 January 21, 2025.
To help decide which airline to fly from Illinois to Florida Keys, see what other customers have to say about Frontier, Delta and American Airlines. 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.
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,662 reviews
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,706 reviews
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,521 reviews
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,201 reviews
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
8,985 reviews
8.1
Very good
4,662 reviews

Food

7.2

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, which is currently one of the cheapest options available, starting at $54. Spirit Airlines flights start at $65 while deals on United 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, 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 $531). 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.

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$487FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$247Average$485FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$484FlexibilityNo cancel feeOn-time69%
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