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$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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This CheapOair deal was found by Cheapflights users on 12/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 12/17$104
This Frontier deal was found by Cheapflights users on 12/17. 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.
Wed 12/315:30 amMIA - MDW
1 stop8h 51mFrontier
Mon 1/123:01 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/17$111
This Booking.com deal was found by Cheapflights users on 12/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Sun 1/116:57 pmORD - MIA
Nonstop3h 17mSpirit Airlines
Deal found 12/16$115
This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:10 pmMIA - MDW
Nonstop3h 27mFrontier
Wed 1/73:01 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/16$119
This Frontier deal was found by Cheapflights users on 12/17. 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.
Wed 12/3112:10 pmMIA - MDW
Nonstop3h 27mFrontier
Thu 1/158:19 pmMDW - MIA
Nonstop3h 09mFrontier
Deal found 12/17$123
This Frontier deal was found by Cheapflights users on 12/17. 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.
Wed 12/315:30 amMIA - MDW
1 stop8h 51mFrontier
Fri 1/168:04 pmMDW - MIA
Nonstop3h 09mFrontier
Deal found 12/17$136
This Spirit deal was found by Cheapflights users on 12/16. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Thu 1/16:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 12/16$138
This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Thu 1/16:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 12/16$139
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Thu 12/252:35 pmMIA - ORD
Nonstop3h 25mMultiple Airlines
Tue 12/306:50 amORD - MIA
1 stop14h 09mMultiple Airlines
Deal found 12/16$141
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/232:35 pmMIA - ORD
Nonstop3h 25mSpirit Airlines
Wed 12/316:05 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 12/16$146
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/307:10 amMIA - ORD
1 stop17h 31mMultiple Airlines
Thu 1/16:05 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Deal found 12/16$148
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/315:54 pmMIA - ORD
1 stop17h 46mMultiple Airlines
Sun 1/46:05 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Deal found 12/16$154

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$84
(Super.com)

One-way from

$59
(Trip.com)
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 December 18, 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

Tue 1/27

1:01 pm-10:38 pm

1 stop10h 37m

Chicago O'Hare Intl

Sat 1/31

6:57 pm-11:14 pm

Nonstop3h 17m

$92

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 1/7

10:13 am-4:00 pm

1 stop6h 47m

Chicago O'Hare Intl

Sat 1/17

9:23 am-1:41 pm

Nonstop3h 18m

$98

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/16

4:29 pm-6:54 pm

Nonstop3h 25m

Chicago Midway

Mon 1/19

6:10 am-2:15 pm

1 stop7h 05m

$130

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 3/7

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Mon 3/9

6:00 am-10:13 am

Nonstop3h 13m

$156

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 1/27

2:35 pm-4:50 pm

Nonstop3h 15m

Chicago Midway

Sat 1/31

5:30 pm-9:30 pm

Nonstop3h 00m

$157

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/5

4:40 pm-6:55 pm

Nonstop3h 15m

Chicago Midway

Sun 2/8

5:30 pm-9:30 pm

Nonstop3h 00m

$157

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sun 2/1

5:30 am-11:45 am

1 stop7h 15m

Chicago Midway

Sun 2/8

5:01 pm-12:47 am

1 stop6h 46m

$174

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Sun 2/1

5:30 am-6:51 am

1 stop26h 21m

Lambert-St Louis

Sun 2/8

8:59 am-11:56 am

2 stops25h 57m

$176

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Mon 3/9

5:13 pm-1:11 am

1 stop6h 58m

$178

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 3/5

5:05 am-4:16 pm

1 stop12h 11m

Chicago Midway

Sun 3/8

6:00 am-10:13 am

Nonstop3h 13m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 December 18, 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 December 18, 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
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
8,190 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
3,081 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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 7h 22m. 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 ($41), Spirit Airlines ($44), and Southwest ($78).

  • 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$427FlexibilityNo cancel feeOn-time71%

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