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$80+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$135
(Cheapflightsfares)

One-way from

$80
(Cheapflightsfares)

Popular in

March

Cheapest in

June

Average price

$406
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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/163:15 pmMIA - ORD
Nonstop3h 26mSpirit Airlines
Mon 5/199:55 amORD - MIA
Nonstop3h 15mSpirit Airlines
Deal found 4/30$135
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/3010:59 pmMIA - ORD
1 stop9h 05mMultiple Airlines
Sun 6/18:17 amORD - MIA
Nonstop3h 13mMultiple Airlines
Deal found 4/29$155
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/37:00 amMIA - MDW
Nonstop3h 10mSouthwest
Wed 6/45:10 pmMDW - MIA
Nonstop2h 55mSouthwest
Deal found 4/30$197
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/309:27 pmMIA - ORD
Nonstop3h 29mAmerican Airlines
Sun 6/14:50 pmORD - MIA
Nonstop3h 08mAmerican Airlines
Deal found 4/30$198
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/297:24 pmMIA - MDW
1 stop25h 19mFrontier
Mon 6/27:05 amMDW - MIA
1 stop24h 00mFrontier
Deal found 4/30$205
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Sat 5/317:35 pmMIA - ORD
1 stop22h 40mFrontier
Sun 6/19:56 pmORD - MIA
1 stop30h 48mFrontier
Deal found 4/30$208
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/145:30 amMIA - ORD
1 stop8h 00mDelta
Sat 6/216:15 pmORD - MIA
1 stop5h 42mDelta
Deal found 4/29$217
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/48:10 amMIA - MDW
1 stop4h 43mDelta
Tue 6/1712:44 pmMDW - MIA
1 stop7h 32mDelta
Deal found 4/30$217
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/26:00 amMIA - STL
1 stop28h 59mFrontier
Sat 5/38:15 pmSTL - MIA
1 stop8h 07mFrontier
Deal found 4/30$218
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/218:18 pmMIA - STL
Nonstop3h 01mAmerican Airlines
Wed 5/286:20 pmSTL - MIA
Nonstop2h 48mAmerican Airlines
Deal found 4/30$230
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/34:35 pmMIA - STL
Nonstop2h 55mSouthwest
Wed 7/98:05 amSTL - MIA
Nonstop2h 50mSouthwest
Deal found 4/30$241
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2110:37 amMIA - STL
1 stop4h 58mDelta
Wed 5/286:00 amSTL - MIA
1 stop6h 15mDelta
Deal found 4/30$250

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 May 1, 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 5/16

3:15 pm-5:41 pm

Nonstop3h 26m

Chicago O'Hare Intl

Mon 5/19

9:55 am-2:10 pm

Nonstop3h 15m

$135

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 5/30

10:59 pm-7:04 am

1 stop9h 05m

Chicago O'Hare Intl

Sun 6/1

8:17 am-12:30 pm

Nonstop3h 13m

$155

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 7/2

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

Sat 7/5

7:10 pm-11:10 pm

Nonstop3h 00m

$179

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 5/30

9:27 pm-11:56 pm

Nonstop3h 29m

Chicago O'Hare Intl

Sun 6/1

4:50 pm-8:58 pm

Nonstop3h 08m

$198

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/29

7:24 pm-7:43 pm

1 stop25h 19m

Chicago Midway

Mon 6/2

7:05 am-8:05 am

1 stop24h 00m

$205

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 5/31

7:35 pm-5:15 pm

1 stop22h 40m

Chicago O'Hare Intl

Sun 6/1

9:56 pm-5:44 am

1 stop30h 48m

$208

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 6/14

5:30 am-12:30 pm

1 stop8h 00m

Chicago O'Hare Intl

Sat 6/21

6:15 pm-12:57 am

1 stop5h 42m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 6/14

5:30 am-9:41 am

1 stop5h 11m

Chicago Midway

Tue 6/17

12:44 pm-9:16 pm

1 stop7h 32m

$217

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 5/21

8:18 pm-10:19 pm

Nonstop3h 01m

Lambert-St Louis

Wed 5/28

6:20 pm-10:08 pm

Nonstop2h 48m

$230

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Thu 7/3

4:35 pm-6:30 pm

Nonstop2h 55m

Lambert-St Louis

Wed 7/9

8:05 am-11:55 am

Nonstop2h 50m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 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 May 1, 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.

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 May 1, 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
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Comfort

7.9

Food

7.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 ($80), Southwest ($90), and Frontier ($98).

  • 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$259Average$388FlexibilityNo cancel feeOn-time71%

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