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Illinois

$55+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/268:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Wed 12/311:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Deal found 10/29$96
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:05 pmMIA - MDW
Nonstop3h 17mFrontier
Mon 11/171:37 pmMDW - MIA
1 stop9h 57mFrontier
Deal found 10/28$96
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/3112:10 pmMIA - MDW
Nonstop3h 27mMultiple Airlines
Tue 1/66:00 amMDW - MIA
1 stop14h 04mMultiple Airlines
Deal found 10/29$98
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:26 pmMIA - MDW
Nonstop3h 27mFrontier
Sat 12/66:00 amMDW - MIA
1 stop8h 39mFrontier
Deal found 10/30$99
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/258:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Tue 12/211:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Deal found 10/30$100
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:30 amMIA - MDW
1 stop17h 42mFrontier
Wed 1/73:52 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 10/30$100
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/114:08 pmMIA - ORD
Nonstop3h 28mMultiple Airlines
Mon 12/1511:01 amORD - MIA
1 stop11h 17mMultiple Airlines
Deal found 10/29$103
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/25:58 pmMIA - MDW
1 stop15h 48mFrontier
Sat 12/62:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 10/29$104
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:20 amMIA - ORD
Nonstop3h 27mSpirit Airlines
Sun 11/1612:17 pmORD - MIA
Nonstop3h 05mSpirit Airlines
Deal found 10/29$105
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:58 pmMIA - MDW
1 stop15h 48mFrontier
Thu 12/42:16 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 10/30$105
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Sat 12/67:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 10/30$106
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/124:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Sun 12/147:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 10/30$107

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$96
(Cheapflightsfares)

One-way from

$55
(Priceline)
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
Search Deals
From Florida Keys to Illinois
Search Deals
One-way flight from Florida Keys to Illinois
Search Deals

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 October 30, 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

Thu 11/27

8:10 am-10:35 am

Nonstop3h 25m

Chicago O'Hare Intl

Tue 12/2

11:40 am-3:47 pm

Nonstop3h 07m

$100

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 11/14

7:20 am-9:47 am

Nonstop3h 27m

Chicago O'Hare Intl

Mon 11/17

12:17 pm-4:22 pm

Nonstop3h 05m

$121

MiamiChicago

MIA - ORD

MIAORD

Miami

Sun 11/23

6:51 pm-5:30 pm

1 stop23h 39m

Chicago O'Hare Intl

Fri 11/28

11:40 am-3:47 pm

Nonstop3h 07m

$143

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Fri 12/5

5:30 am-9:47 am

1 stop5h 17m

Lambert-St Louis

Sun 12/7

10:42 am-10:48 am

1 stop23h 06m

$156

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 1/7

2:35 pm-4:50 pm

Nonstop3h 15m

Chicago Midway

Sun 1/11

9:40 am-1:45 pm

Nonstop3h 05m

$157

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/16

6:05 pm-10:25 pm

1 stop5h 20m

Chicago Midway

Mon 1/19

9:40 am-1:45 pm

Nonstop3h 05m

$167

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 1/15

6:05 pm-10:25 pm

1 stop5h 20m

Chicago Midway

Tue 1/20

5:00 am-12:05 pm

1 stop6h 05m

$177

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 11/6

7:07 pm-12:11 am

1 stop6h 04m

Chicago O'Hare Intl

Sun 11/9

12:17 pm-4:22 pm

Nonstop3h 05m

$191

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 12/23

2:35 pm-5:00 pm

Nonstop3h 25m

Chicago O'Hare Intl

Fri 1/2

7:57 pm-9:15 am

1 stop12h 18m

$206

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Mon 11/17

8:25 am-8:12 pm

2 stops12h 47m

Lambert-St Louis

Thu 11/20

3:14 pm-11:23 am

1 stop19h 09m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 October 30, 2025.

One of the essential ways to save on airfare from Florida Keys to Illinois is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 27% on airfare.

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 October 30, 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
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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 Spirit Airlines, Frontier, and Southwest fly from Florida Keys to Illinois in about 3h 15m. The time it takes to get you to your destination can typically vary by up to 2h 02m. The distance from Florida Keys to Illinois is about 1183 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Frontier ($55), Spirit Airlines ($68), and United Airlines ($79).

  • 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.

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$499FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$398FlexibilityNo cancel feeOn-time71%

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