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Illinois

$68+ Cheap flights from Florida Keys to Illinois

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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Florida Keys to Illinois

Keep the following information in mind while searching for Florida Keys to Illinois flight deals. Data was last updated July 31, 2025.

Round-trip from

$131
(Kiwi.com)

One-way from

$68
(Cheapflightsfares)

Popular in

March

Cheapest in

June

Average price

$358
From Florida Keys to Illinois
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One-way flight from Florida Keys to Illinois
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Highest demand for flights based on searches. 17% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Florida Keys to Illinois

Cheapest flights from Florida Keys to Illinois
Explore the most affordable flight options available from Florida Keys to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Sat 10/186:00 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Thu 10/3010:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Deal found 7/31$131
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/66:20 amMIA - ORD
Nonstop3h 20mAmerican Airlines
Mon 9/87:25 pmORD - MIA
Nonstop3h 10mAmerican Airlines
Deal found 7/28$137
This Southwest deal was found by Cheapflights users on 7/30. 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.
Fri 9/1912:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Sun 9/212:45 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 7/30$137
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 8/156:42 pmMIA - ORD
1 stop6h 40mMultiple Airlines
Wed 8/2010:27 amORD - MIA
Nonstop3h 22mMultiple Airlines
Deal found 7/29$152
This Frontier deal was found by Cheapflights users on 7/31. 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 10/166:53 pmMIA - MDW
Nonstop3h 15mFrontier
Mon 10/2710:03 pmMDW - MIA
Nonstop3h 00mFrontier
Deal found 7/31$156
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 9/197:10 amMIA - ORD
1 stop5h 40mSouthwest
Mon 9/226:00 amORD - MIA
1 stop4h 50mSouthwest
Deal found 7/31$157
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/2310:09 pmMIA - STL
Nonstop2h 50mAmerican Airlines
Wed 8/275:26 amSTL - MIA
Nonstop2h 48mAmerican Airlines
Deal found 7/29$189
This FlightHub deal was found by Cheapflights users on 7/29. 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 8/203:40 pmMIA - STL
1 stop22h 52mSpirit Airlines
Sun 8/242:30 pmSTL - MIA
1 stop17h 48mSpirit Airlines
Deal found 7/29$197
This Delta deal was found by Cheapflights users on 7/30. 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 8/206:00 amMIA - STL
1 stop7h 31mDelta
Tue 9/23:36 pmSTL - MIA
1 stop4h 52mDelta
Deal found 7/30$203
This Delta deal was found by Cheapflights users on 7/30. 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 9/68:10 amMIA - MDW
1 stop5h 18mDelta
Mon 9/81:08 pmMDW - MIA
1 stop7h 22mDelta
Deal found 7/30$215
This Frontier deal was found by Cheapflights users on 7/31. 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.
Sat 8/237:05 amMIA - STL
1 stop7h 28mFrontier
Sat 8/303:02 pmSTL - MIA
1 stop7h 24mFrontier
Deal found 7/31$218
This Southwest deal was found by Cheapflights users on 7/31. 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 8/305:50 amMIA - STL
Nonstop2h 50mSouthwest
Mon 9/15:30 amSTL - MIA
1 stop9h 50mSouthwest
Deal found 7/31$248

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys to Illinois 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 July 31, 2025.
Use the filters below to find and compare flights from Florida Keys to Illinois that are best for you.

Fly from

Florida Keys

Fly to

Illinois

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 10/18

6:00 am-8:15 am

Nonstop3h 15m

Chicago O'Hare Intl

Thu 10/30

10:27 am-2:39 pm

Nonstop3h 12m

$131

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 9/6

6:20 am-8:40 am

Nonstop3h 20m

Chicago O'Hare Intl

Mon 9/8

7:25 pm-11:35 pm

Nonstop3h 10m

$137

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 9/19

12:35 pm-2:45 pm

Nonstop3h 10m

Chicago Midway

Sun 9/21

2:45 pm-6:45 pm

Nonstop3h 00m

$137

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 8/15

6:42 pm-12:22 am

1 stop6h 40m

Chicago O'Hare Intl

Wed 8/20

10:27 am-2:49 pm

Nonstop3h 22m

$152

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 10/16

6:53 pm-9:08 pm

Nonstop3h 15m

Chicago Midway

Mon 10/27

10:03 pm-2:03 am

Nonstop3h 00m

$156

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 9/19

7:10 am-11:50 am

1 stop5h 40m

Chicago O'Hare Intl

Mon 9/22

6:00 am-11:50 am

1 stop4h 50m

$157

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Sat 8/23

10:09 pm-11:59 pm

Nonstop2h 50m

Lambert-St Louis

Wed 8/27

5:26 am-9:14 am

Nonstop2h 48m

$189

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 8/20

3:40 pm-1:32 pm

1 stop22h 52m

Lambert-St Louis

Sun 8/24

2:30 pm-9:18 am

1 stop17h 48m

$197

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 8/20

6:00 am-12:31 pm

1 stop7h 31m

Lambert-St Louis

Tue 9/2

3:36 pm-9:28 pm

1 stop4h 52m

$203

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 9/6

8:10 am-12:28 pm

1 stop5h 18m

Chicago Midway

Mon 9/8

1:08 pm-9:30 pm

1 stop7h 22m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 57 results
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Best time to book a flight from Florida Keys to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Florida Keys 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 Florida Keys to Illinois

What is the cheapest month to book a flight from Florida Keys to Illinois?

Currently, August is the cheapest month in which you can book a flight from Florida Keys to Illinois (average of $245). Flying from Florida Keys to Illinois in March is currently the most expensive (average of $321). 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 EOA to IL?

Find hourly flight availability from Florida Keys to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Florida Keys to Illinois as you normally would.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated July 31, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Florida Keys to Illinois by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Illinois. 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 Florida Keys to Illinois one-way?

    The cheapest airlines for a one-way flight from Florida Keys to Illinois are Spirit Airlines ($68), American Airlines ($69), and Southwest ($69).

  • Can I find deals for flights from Florida Keys to Illinois that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Illinois.

  • Can I find deals for business class flights from Florida Keys to Illinois?

    Yes. Cheapflights offers flight deals from Florida Keys to Illinois 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 Florida Keys to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Florida Keys to Illinois (average of $245). Flying from Florida Keys to Illinois in March is currently the most expensive (average of $321). 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

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Alternative routes for Florida Keys to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Florida Keys to Illinois

Discover the top 2 airlines that operate flights from Florida Keys to Illinois. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$377FlexibilityNo cancel feeOn-time71%

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