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$160+ Cheap flights from Fort Myers to Milwaukee (RSW - MKE)

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.
RSW — MKE
May 11 — May 181
Mon 5/11
Mon 5/18
1 adult, Economy
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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Milwaukee-Mitchell are usually found in September or October, booked 26 days in advance, depart on a Sunday or Thursday and return on a Monday

Cheap flight deals from Fort Myers to Milwaukee

Cheapest flights from Fort Myers to Milwaukee
Explore the most affordable flight options available from Fort Myers to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2026.

This Southwest deal was found by Cheapflights users on 4/6. 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.
Wed 5/205:45 pm
RSW
-
MKE
1 stop6h 05m
Southwest
Tue 6/26:50 am
MKE
-
RSW
Nonstop2h 50m
Southwest
Deal found 4/6$331
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Wed 5/66:54 pm
RSW
-
MKE
1 stop5h 35m
American Airlines
Tue 5/1211:13 am
MKE
-
RSW
1 stop5h 21m
American Airlines
Deal found 4/6$341
This United Airlines deal was found by Cheapflights users on 4/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:15 pm
RSW
-
MKE
2 stops9h 48m
United Airlines
Tue 6/25:00 am
MKE
-
RSW
1 stop5h 24m
United Airlines
Deal found 4/6$346
This Southwest deal was found by Cheapflights users on 4/10. 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.
Wed 5/135:45 pm
RSW
-
MKE
1 stop6h 05m
Southwest
Thu 5/142:40 pm
MKE
-
RSW
Nonstop2h 50m
Southwest
Deal found 4/10$357
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:30 am
RSW
-
MKE
2 stops9h 25m
Southwest
Tue 5/126:50 am
MKE
-
RSW
Nonstop2h 50m
Southwest
Deal found 4/7$362
This Delta deal was found by Cheapflights users on 4/10. 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 5/55:30 pm
RSW
-
MKE
1 stop7h 27m
Delta
Thu 5/146:25 pm
MKE
-
RSW
1 stop5h 02m
Delta
Deal found 4/10$367
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Sat 5/99:00 am
RSW
-
MKE
2 stops9h 07m
United Airlines
Tue 5/128:33 am
MKE
-
RSW
1 stop5h 04m
United Airlines
Deal found 4/7$372
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:50 am
RSW
-
MKE
Nonstop3h 10m
Southwest
Sat 5/26:50 am
MKE
-
RSW
Nonstop2h 50m
Southwest
Deal found 4/7$373
This Delta deal was found by Cheapflights users on 4/10. 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.
Mon 5/47:50 am
RSW
-
MKE
1 stop4h 37m
Delta
Thu 5/76:25 pm
MKE
-
RSW
1 stop5h 02m
Delta
Deal found 4/10$383

Find flight deals from Fort Myers to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$331
(Southwest)

One-way from

$160
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$466
Provider with most accurate pricing for Fort Myers SW Florida Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Milwaukee-Mitchell flights.
Search Deals
From Fort Myers SW Florida Intl to Milwaukee-Mitchell
Search Deals
One-way flight from Fort Myers SW Florida Intl to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to Milwaukee 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 11, 2026.
Use the filters below to find and compare flights from Fort Myers to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Wed 5/20

5:45 pm-10:50 pm

1 stop6h 05m

Milwaukee-Mitchell

Tue 6/2

6:50 am-10:40 am

Nonstop2h 50m

$331

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Tue 5/5

5:30 pm-11:57 pm

1 stop7h 27m

Milwaukee-Mitchell

Thu 5/14

6:25 pm-12:27 am

1 stop5h 02m

$367

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Mon 6/1

6:35 am-12:10 pm

2 stops6h 35m

Milwaukee-Mitchell

Mon 6/1

2:40 pm-6:30 pm

Nonstop2h 50m

$388

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Wed 6/17

5:37 am-9:03 am

1 stop4h 26m

Milwaukee-Mitchell

Fri 6/26

12:56 pm-9:10 pm

1 stop7h 14m

$395

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Tue 6/16

10:53 am-4:32 pm

1 stop6h 39m

Milwaukee-Mitchell

Fri 6/26

12:56 pm-6:53 pm

1 stop4h 57m

$405

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Wed 6/17

1:05 pm-11:10 pm

2 stops11h 05m

Milwaukee-Mitchell

Tue 6/30

8:05 am-4:40 pm

2 stops7h 35m

$406
Quickest round-trip

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Thu 5/21

11:50 am-2:00 pm

Nonstop3h 10m

Milwaukee-Mitchell

Sun 5/24

9:00 am-2:25 pm

1 stop4h 25m

$406

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Thu 6/4

3:45 pm-9:02 pm

1 stop6h 17m

Milwaukee-Mitchell

Sun 6/7

6:40 pm-1:01 am

1 stop5h 21m

$411

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Fri 5/1

12:55 pm-11:10 pm

2 stops11h 15m

Milwaukee-Mitchell

Tue 5/5

6:50 am-10:40 am

Nonstop2h 50m

$417
Cheapest one-way

Fort MyersMilwaukee

RSW - MKE

RSWMKE

Fort Myers SW Florida Intl

Tue 6/9

2:29 pm-9:43 pm

1 stop8h 14m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Fort Myers to Milwaukee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Fort Myers to Milwaukee in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Fort Myers-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Fort Myers-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Fort Myers to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Fort Myers 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 Fort Myers to Milwaukee

How far ahead should I book a flight from Fort Myers to Milwaukee?

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to Milwaukee. Price data was last updated on April 9, 2026.

To ensure you get the cheapest price possible for a flight from Fort Myers to Milwaukee, you should look to book at least 26 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Fort Myers to Milwaukee?

Currently, May is the cheapest month in which you can book a flight from Fort Myers to Milwaukee (average of $58). Flying from Fort Myers to Milwaukee in June is currently the most expensive (average of $113). 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 RSW to MKE?

Find hourly flight availability from Fort Myers to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 11, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 48% on flights from Fort Myers to Milwaukee by exploring options for tickets in the evening.

How much does it cost to fly round-trip from Fort Myers to Milwaukee?

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated April 11, 2026.
See what other customers who have flown with Southwest,Delta, andAmerican Airlines from Fort Myers to Milwaukee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,406 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,569 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Sun Country Air
6.8
Okay
335 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Fort Myers to Milwaukee flight route?

    The Fort Myers SW Florida Intl to Milwaukee-Mitchell flight path was viewed by 3 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Fort Myers to Milwaukee?

    Airlines like Southwest and Delta fly from Fort Myers to Milwaukee in about 6h 05m. The time it takes to get you to your destination can typically vary by up to 1h 22m. The distance from Fort Myers to Milwaukee is about 1184 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 flying from Fort Myers to Milwaukee round-trip?

    Flying on Sun Country Air is currently your cheapest option to Milwaukee, with prices starting at $79. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $209 and $259, respectively. Sun Country Air is priced at 80% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Fort Myers to Milwaukee one-way?

    To fly one-way, consider booking your trip with Sun Country Air, which is currently one of the cheapest options available, starting at $79. American Airlines flights start at $109 while deals on United Airlines start at $115 one-way.

  • What are the cheapest flights from Fort Myers to Milwaukee?

    While on average a flight from Fort Myers to Milwaukee is generally $343, our data shows the cheapest flight currently is $133. When looking at the most popular route, (Fort Myers SW Florida Intl - Milwaukee-Mitchell), you can expect to pay $341 for that flight.

  • Can I find deals for flights from Fort Myers to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Fort Myers to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Fort Myers to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Fort Myers to Milwaukee.

  • Can I find deals for business class flights from Fort Myers to Milwaukee?

    Yes. Cheapflights offers flight deals from Fort Myers to Milwaukee 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 Fort Myers to Milwaukee?

    Currently, May is the cheapest month in which you can book a flight from Fort Myers to Milwaukee (average of $58). Flying from Fort Myers to Milwaukee in June is currently the most expensive (average of $113). 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

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa

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Top 4 airlines flying from Fort Myers to Milwaukee

Discover the top 4 airlines that operate flights from Fort Myers to Milwaukee. 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 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Sun Country AirCheapest$79Average$298FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$209Average$366FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$259Average$431FlexibilityNo cancel feeOn-time63%
DeltaCheapest$287Average$458FlexibilityNo cancel feeOn-timeN/A

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