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$77+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$129
(Cheapflightsfares)

One-way from

$77
(eDestinos)

Popular in

March

Cheapest in

June

Average price

$411
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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Highest demand for flights based on searches. 17% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 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 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 5/73:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Wed 5/79:14 pmORD - MIA
1 stop10h 51mSpirit Airlines
Deal found 4/22$129
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/97:12 amMIA - ORD
1 stop9h 45mMultiple Airlines
Tue 5/139:55 amORD - MIA
Nonstop3h 15mMultiple Airlines
Deal found 4/23$150
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/249:27 pmMIA - ORD
Nonstop3h 29mAmerican Airlines
Sun 5/251:41 pmORD - MIA
Nonstop3h 11mAmerican Airlines
Deal found 4/23$179
This Southwest deal was found by Cheapflights users on 4/23. 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.
Thu 7/36:45 amMIA - MDW
Nonstop3h 10mSouthwest
Mon 7/78:00 amMDW - MIA
Nonstop3h 00mSouthwest
Deal found 4/23$188
This Frontier deal was found by Cheapflights users on 4/23. 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 5/26:00 amMIA - ORD
1 stop8h 20mFrontier
Thu 5/86:00 amORD - MIA
1 stop8h 00mFrontier
Deal found 4/23$198
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/136:00 amMIA - STL
1 stop28h 59mFrontier
Wed 6/118:11 pmSTL - MIA
1 stop9h 19mFrontier
Deal found 4/21$199
This eDestinos deal was found by Cheapflights users on 4/23. 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 5/3010:59 pmMIA - MDW
1 stop24h 18mFrontier
Tue 6/34:54 pmMDW - MIA
1 stop14h 11mFrontier
Deal found 4/23$212
This Delta deal was found by Cheapflights users on 4/23. 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 5/245:59 pmMIA - ORD
1 stop6h 18mDelta
Sun 5/2510:30 amORD - MIA
1 stop6h 37mDelta
Deal found 4/23$217
This Delta deal was found by Cheapflights users on 4/23. 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 5/218:10 amMIA - MDW
1 stop4h 43mDelta
Tue 5/279:16 amMDW - MIA
1 stop7h 46mDelta
Deal found 4/23$218
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 5/213:30 pmMIA - STL
Nonstop2h 59mAmerican Airlines
Wed 5/286:20 pmSTL - MIA
Nonstop2h 48mAmerican Airlines
Deal found 4/23$220
This Delta deal was found by Cheapflights users on 4/21. 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 5/145:35 amMIA - STL
1 stop7h 29mDelta
Tue 6/1010:30 amSTL - MIA
1 stop5h 40mDelta
Deal found 4/21$240
This Southwest deal was found by Cheapflights users on 4/22. 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.
Tue 6/37:55 amMIA - STL
Nonstop2h 55mSouthwest
Tue 6/108:05 amSTL - MIA
Nonstop2h 50mSouthwest
Deal found 4/22$241

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 24, 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

Wed 5/7

3:15 pm-5:41 pm

Nonstop3h 26m

Chicago O'Hare Intl

Wed 5/7

9:14 pm-9:05 am

1 stop10h 51m

$129

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 5/9

7:12 am-3:57 pm

1 stop9h 45m

Chicago O'Hare Intl

Tue 5/13

9:55 am-2:10 pm

Nonstop3h 15m

$150

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 5/24

9:27 pm-11:56 pm

Nonstop3h 29m

Chicago O'Hare Intl

Sun 5/25

1:41 pm-5:52 pm

Nonstop3h 11m

$179

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 7/3

6:45 am-8:55 am

Nonstop3h 10m

Chicago Midway

Mon 7/7

8:00 am-12:00 pm

Nonstop3h 00m

$188

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 5/8

3:55 pm-11:11 pm

1 stop8h 16m

Chicago O'Hare Intl

Mon 5/12

5:21 pm-5:22 am

1 stop11h 01m

$198

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Tue 5/13

6:00 am-9:59 am

1 stop28h 59m

Lambert-St Louis

Wed 6/11

8:11 pm-6:30 am

1 stop9h 19m

$199

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 5/30

10:59 pm-10:17 pm

1 stop24h 18m

Chicago Midway

Tue 6/3

4:54 pm-8:05 am

1 stop14h 11m

$212

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 5/24

5:59 pm-11:17 pm

1 stop6h 18m

Chicago O'Hare Intl

Sun 5/25

10:30 am-6:07 pm

1 stop6h 37m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 5/21

8:10 am-11:53 am

1 stop4h 43m

Chicago Midway

Tue 5/27

9:16 am-6:02 pm

1 stop7h 46m

$218

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 5/21

3:30 pm-5:29 pm

Nonstop2h 59m

Lambert-St Louis

Wed 5/28

6:20 pm-10:08 pm

Nonstop2h 48m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 24, 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 24, 2025.

The most flights from zzEOA to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 24, 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
9,918 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Comfort

7.9

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 ($77), Frontier ($78), and American Airlines ($90).

  • 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 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$388FlexibilityNo cancel feeOn-time71%

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