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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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$125
(Cheapflightsfares)

One-way from

$68
(Cheapflightsfares)

Popular in

July

Cheapest in

August

Average price

$386
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
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From Florida Keys to Illinois
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One-way flight from Florida Keys to Illinois
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High demand for flights, 6% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 5/93:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Tue 5/139:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Deal found 4/2$125
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/249:04 amMIA - ORD
1 stop6h 00mMultiple Airlines
Tue 4/297:00 pmORD - MIA
Nonstop3h 12mMultiple Airlines
Deal found 4/1$150
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 4/1511:03 amMIA - MDW
Nonstop3h 28mFrontier
Thu 4/178:00 amMDW - MIA
Nonstop3h 08mFrontier
Deal found 4/1$151
This Southwest deal was found by Cheapflights users on 4/1. 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 5/105:05 amMIA - MDW
Nonstop3h 10mSouthwest
Sun 5/118:40 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 4/1$177
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Thu 5/16:25 amMIA - ORD
Nonstop3h 23mAmerican Airlines
Sat 5/37:17 pmORD - MIA
Nonstop3h 12mAmerican Airlines
Deal found 4/1$178
This Frontier deal was found by Cheapflights users on 4/1. 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 5/16:00 amMIA - STL
1 stop10h 07mFrontier
Fri 5/26:53 pmSTL - MIA
1 stop9h 29mFrontier
Deal found 4/1$198
This Frontier deal was found by Cheapflights users on 4/2. 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.
Fri 5/210:01 amMIA - ORD
1 stop10h 17mFrontier
Mon 5/58:40 amORD - MIA
1 stop6h 42mFrontier
Deal found 4/2$198
This FlightHub deal was found by Cheapflights users on 4/1. 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.
Thu 11/67:58 pmMIA - STL
1 stop12h 51mSpirit Airlines
Sun 11/98:44 amSTL - MIA
1 stop9h 09mSpirit Airlines
Deal found 4/1$205
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Sat 4/197:00 amMIA - ORD
Nonstop3h 32mUnited Airlines
Tue 4/227:30 amORD - MIA
Nonstop3h 18mUnited Airlines
Deal found 4/1$214
This Delta deal was found by Cheapflights users on 4/2. 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 4/2910:25 amMIA - ORD
1 stop5h 05mDelta
Tue 5/611:15 amORD - MIA
1 stop7h 33mDelta
Deal found 4/2$217
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/297:00 amMIA - MDW
1 stop6h 03mDelta
Wed 5/712:48 pmMDW - MIA
1 stop4h 37mDelta
Deal found 3/31$217
This Delta deal was found by Cheapflights users on 4/1. 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 4/226:00 amMIA - STL
1 stop4h 36mDelta
Tue 4/295:32 pmSTL - MIA
1 stop6h 16mDelta
Deal found 4/1$239

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 April 2, 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

Fri 5/9

3:15 pm-5:41 pm

Nonstop3h 26m

Chicago O'Hare Intl

Tue 5/13

9:55 am-2:10 pm

Nonstop3h 15m

$125

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 4/24

9:04 am-2:04 pm

1 stop6h 00m

Chicago O'Hare Intl

Tue 4/29

7:00 pm-11:12 pm

Nonstop3h 12m

$150

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 4/15

11:03 am-1:31 pm

Nonstop3h 28m

Chicago Midway

Thu 4/17

8:00 am-12:08 pm

Nonstop3h 08m

$151

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 5/10

5:05 am-7:15 am

Nonstop3h 10m

Chicago Midway

Mon 5/12

6:35 pm-10:30 pm

Nonstop2h 55m

$177

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 5/1

6:25 am-8:48 am

Nonstop3h 23m

Chicago O'Hare Intl

Sat 5/3

7:17 pm-11:29 pm

Nonstop3h 12m

$178

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 4/24

9:04 am-2:04 pm

1 stop6h 00m

Chicago O'Hare Intl

Sun 4/27

8:00 am-2:43 pm

1 stop5h 43m

$196

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Thu 5/1

6:00 am-3:07 pm

1 stop10h 07m

Lambert-St Louis

Fri 5/2

6:53 pm-5:22 am

1 stop9h 29m

$198

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 4/19

7:00 am-9:32 am

Nonstop3h 32m

Chicago O'Hare Intl

Tue 4/22

7:30 am-11:48 am

Nonstop3h 18m

$214

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 4/29

10:25 am-2:30 pm

1 stop5h 05m

Chicago O'Hare Intl

Tue 5/6

11:15 am-7:48 pm

1 stop7h 33m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 4/29

4:47 pm-10:22 pm

1 stop6h 35m

Chicago Midway

Tue 5/6

9:52 am-3:38 pm

1 stop4h 46m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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 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 April 2, 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.

Weekly flight availability from Florida Keys to Illinois

Explore weekly flight availability from Florida Keys to Illinois. 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 April 2, 2025.

The most flights from zzEOA to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 2, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Florida Keys to Illinois. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,820 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,820 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,898 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,616 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Allegiant Air
7.3
Good
731 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Frontier ($68), Spirit Airlines ($69), and Southwest ($89).

  • 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$379FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$239Average$388FlexibilityNo cancel feeOn-time71%

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