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Illinois

$59+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$107
(Cheapflightsfares)

One-way from

$59
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$288
From Florida Keys to Illinois
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One-way flight from Florida Keys to Illinois
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/107:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Sat 10/119:27 amORD - MIA
Nonstop3h 03mSpirit Airlines
Deal found 9/15$107
This Spirit deal was found by Cheapflights users on 9/14. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Sat 10/410:27 amORD - MIA
Nonstop3h 12mSpirit Airlines
Deal found 9/14$108
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/1910:15 amMIA - ORD
Nonstop3h 15mSpirit Airlines
Tue 12/21:35 pmORD - MIA
Nonstop3h 15mSpirit Airlines
Deal found 9/15$109
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:28 amMIA - ORD
1 stop7h 22mMultiple Airlines
Mon 10/610:27 amORD - MIA
Nonstop3h 02mMultiple Airlines
Deal found 9/15$110
This eDestinos deal was found by Cheapflights users on 9/16. 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 10/249:00 amMIA - MDW
Nonstop3h 17mFrontier
Mon 10/2712:17 pmMDW - MIA
Nonstop3h 01mFrontier
Deal found 9/16$112
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:59 pmMIA - ORD
1 stop6h 11mMultiple Airlines
Wed 10/110:27 amORD - MIA
Nonstop3h 12mMultiple Airlines
Deal found 9/15$115
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:00 amMIA - ORD
1 stop8h 12mMultiple Airlines
Tue 9/3010:27 amORD - MIA
Nonstop3h 12mMultiple Airlines
Deal found 9/15$116
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Wed 10/17:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Sun 10/510:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/14$117
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Thu 10/910:27 amORD - MIA
Nonstop3h 02mSpirit Airlines
Deal found 9/14$119
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:47 pmMIA - MDW
1 stop6h 00mFrontier
Fri 10/1710:33 amMDW - MIA
Nonstop3h 00mFrontier
Deal found 9/16$119
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/317:00 amMIA - ORD
Nonstop3h 22mMultiple Airlines
Fri 11/78:26 amORD - MIA
1 stop8h 15mMultiple Airlines
Deal found 9/16$120
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/109:10 amMIA - MDW
Nonstop3h 17mFrontier
Tue 10/148:05 amMDW - MIA
1 stop5h 27mFrontier
Deal found 9/13$120

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 September 16, 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

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Thu 10/23

10:01 pm-11:56 pm

Nonstop2h 55m

Lambert-St Louis

Sun 10/26

6:08 pm-9:50 pm

Nonstop2h 42m

$131

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 10/8

10:01 pm-11:56 pm

Nonstop2h 55m

Lambert-St Louis

Sun 10/12

6:08 pm-9:50 pm

Nonstop2h 42m

$131

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 10/15

4:17 pm-6:47 pm

Nonstop3h 30m

Chicago O'Hare Intl

Sat 10/18

10:54 am-3:11 pm

Nonstop3h 17m

$157

MiamiChicago

MIA - ORD

MIAORD

Miami

Sun 11/9

7:00 am-9:29 am

Nonstop3h 29m

Chicago O'Hare Intl

Wed 11/12

10:35 am-2:50 pm

Nonstop3h 15m

$177

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sun 11/9

6:20 am-8:35 am

Nonstop3h 15m

Chicago Midway

Wed 11/12

12:25 pm-8:25 pm

1 stop7h 00m

$187

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 11/6

6:20 am-8:35 am

Nonstop3h 15m

Chicago Midway

Mon 11/10

6:20 am-12:40 pm

1 stop5h 20m

$187

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Thu 10/23

3:35 pm-5:28 pm

Nonstop2h 53m

Lambert-St Louis

Wed 11/5

5:15 am-8:59 am

Nonstop2h 44m

$191

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 11/5

8:28 pm-10:27 pm

Nonstop2h 59m

Lambert-St Louis

Sun 11/16

5:15 am-8:59 am

Nonstop2h 44m

$195

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 10/15

7:10 am-12:35 pm

1 stop6h 25m

Lambert-St Louis

Tue 10/21

7:05 am-3:30 pm

1 stop7h 25m

$197

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 10/8

10:40 am-3:55 pm

1 stop6h 15m

Lambert-St Louis

Sun 10/12

6:00 am-1:11 pm

1 stop6h 11m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 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 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 September 16, 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 September 16, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines 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.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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.
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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.
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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 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.

  • How long is the flight from Florida Keys to Illinois?

    Airlines like American Airlines, United Airlines, and Southwest fly from Florida Keys to Illinois in about 2h 55m. The time it takes to get you to your destination is usually consistent. The distance from Florida Keys to Illinois is about 1069 mi. Most flights are nonstop.

  • 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 ($64), American Airlines ($66), and Frontier ($71).

  • 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

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$398FlexibilityNo cancel feeOn-time71%

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