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Florida Keys

$67+ Cheap flights from Wisconsin to Florida Keys

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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
1 adult, Economy
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Cheap flight deals from Wisconsin to Florida Keys

Keep the following information in mind while searching for Wisconsin to Florida Keys flight deals. Data was last updated August 7, 2025.

Round-trip from

$131
(Mytrip)

One-way from

$67
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$320
From Wisconsin to Florida Keys
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One-way flight from Wisconsin to Florida Keys
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Highest demand for flights based on searches. 11% potential increase in price ($50 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 August 2025
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Find flight deals from Wisconsin to Florida Keys

Cheapest flights from Wisconsin to Florida Keys
Explore the most affordable flight options available from Wisconsin to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 7, 2025.

This Mytrip deal was found by Cheapflights users on 8/6. 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.
Wed 9/38:12 pmORD - MIA
2 stops19h 42mSpirit Airlines
Wed 9/107:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/6$131
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 9/611:12 amORD - MIA
1 stop11h 05mSpirit Airlines
Thu 9/117:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/7$132
This FlightHub deal was found by Cheapflights users on 8/6. 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.
Sat 8/308:47 pmORD - MIA
1 stop12h 27mSpirit Airlines
Tue 9/27:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 8/6$133
This Cheapflightsfares deal was found by Cheapflights users on 8/6. 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.
Mon 8/2510:12 amORD - MIA
1 stop6h 27mSpirit Airlines
Fri 8/297:00 amMIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 8/6$134
This Gotogate deal was found by Cheapflights users on 8/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/611:12 amORD - MIA
1 stop11h 05mSpirit Airlines
Mon 9/87:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/6$135
This Cheapflightsfares deal was found by Cheapflights users on 8/6. 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 10/2410:23 amORD - MIA
Nonstop3h 12mSpirit Airlines
Sun 10/267:00 amMIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 8/6$136
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/266:09 amORD - MIA
Nonstop3h 05mAmerican Airlines
Wed 10/17:00 pmMIA - ORD
Nonstop3h 22mAmerican Airlines
Deal found 8/6$137
This American Airlines deal was found by Cheapflights users on 8/6. 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 9/67:05 amORD - MIA
Nonstop3h 04mAmerican Airlines
Mon 9/87:59 pmMIA - ORD
Nonstop3h 27mAmerican Airlines
Deal found 8/6$138
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Thu 9/47:25 amORD - MIA
Nonstop3h 17mUnited Airlines
Thu 9/1112:27 pmMIA - ORD
Nonstop3h 28mUnited Airlines
Deal found 8/7$140
This American Airlines deal was found by Cheapflights users on 8/6. 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.
Mon 8/257:05 pmORD - MIA
Nonstop3h 19mAmerican Airlines
Sat 8/309:25 pmMIA - ORD
Nonstop3h 32mAmerican Airlines
Deal found 8/6$141
This FlightHub deal was found by Cheapflights users on 8/6. 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.
Wed 10/2210:23 amORD - MIA
Nonstop3h 12mSpirit Airlines
Mon 11/36:00 amMIA - ORD
1 stop12h 38mSpirit Airlines
Deal found 8/6$142
This Southwest deal was found by Cheapflights users on 8/6. 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 9/93:00 pmMKE - MIA
1 stop5h 10mSouthwest
Sat 9/135:10 pmMIA - MKE
1 stop5h 00mSouthwest
Deal found 8/6$158

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Florida Keys 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 August 7, 2025.
Use the filters below to find and compare flights from Wisconsin to Florida Keys that are best for you.

Fly from

Wisconsin

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 9/3

8:12 pm-4:54 pm

2 stops19h 42m

Miami

Wed 9/10

7:00 am-9:18 am

Nonstop3h 18m

$131

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/6

11:12 am-11:17 pm

1 stop11h 05m

Miami

Thu 9/11

7:00 am-9:18 am

Nonstop3h 18m

$132

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 8/30

8:47 pm-10:14 am

1 stop12h 27m

Miami

Tue 9/2

7:00 am-9:22 am

Nonstop3h 22m

$133

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 8/25

10:12 am-5:39 pm

1 stop6h 27m

Miami

Fri 8/29

7:00 am-9:22 am

Nonstop3h 22m

$134

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/6

11:12 am-11:17 pm

1 stop11h 05m

Miami

Mon 9/8

7:00 am-9:18 am

Nonstop3h 18m

$135

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 10/24

10:23 am-2:35 pm

Nonstop3h 12m

Miami

Sun 10/26

7:00 am-9:18 am

Nonstop3h 18m

$136

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/26

6:09 am-10:14 am

Nonstop3h 05m

Miami

Wed 10/1

7:00 pm-9:22 pm

Nonstop3h 22m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/6

7:05 am-11:09 am

Nonstop3h 04m

Miami

Mon 9/8

7:59 pm-10:26 pm

Nonstop3h 27m

$138

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 9/4

7:25 am-11:42 am

Nonstop3h 17m

Miami

Thu 9/11

12:27 pm-2:55 pm

Nonstop3h 28m

$140

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 8/25

7:05 pm-11:24 pm

Nonstop3h 19m

Miami

Sat 8/30

9:25 pm-11:57 pm

Nonstop3h 32m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/6

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Wisconsin 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 Wisconsin to Florida Keys

What is the cheapest month to book a flight from Wisconsin to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Wisconsin to Florida Keys (average of $328). Flying from Wisconsin to Florida Keys in March is currently the most expensive (average of $492). 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.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated August 7, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Wisconsin to Florida Keys. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
701 reviews
Southwest
8.0
Very good
4,247 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Florida Keys. 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 Wisconsin to Florida Keys one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $67. American Airlines flights start at $69 while deals on Southwest start at $79 one-way.

  • Can I find deals for flights from Wisconsin to Florida Keys that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Florida Keys flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Florida Keys?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Florida Keys.

  • Can I find deals for business class flights from Wisconsin to Florida Keys?

    Yes. Cheapflights offers flight deals from Wisconsin to Florida Keys 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 Wisconsin to Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Wisconsin to Florida Keys (average of $328). Flying from Wisconsin to Florida Keys in March is currently the most expensive (average of $492). 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 Wisconsin to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Wisconsin to Florida Keys

Discover the top 4 airlines that operate flights from Wisconsin to Florida Keys. 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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$142Average$273FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$219Average$472FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$552FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$268Average$538FlexibilityNo cancel feeOn-time69%

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