13 CHEAP Places to Fly from Milwaukee This Year

Look, I get it. Flying from Milwaukee can feel expensive, but I’ve found some crazy good deals after spending way too much time glued to flight search engines (my browser history is embarrassing). Last month I scored a $180 roundtrip to Denver and spent my days hiking Rocky Mountain National Park and stuffing my face at Larimer Square.

These are the best places from Milwaukee to visit that won’t make your wallet cry. From dancing through Nashville’s Broadway (found tickets under $150!) to weekend trips to Chicago where you can actually afford the deep-dish pizza, I’ve got 13 destinations that prove you don’t need to be rich to travel. Trust me, your bank account will thank you.

#1 tip for finding cheap flights from Milwaukee

Looking for cheap places to fly from Milwaukee? Before jumping into all the coolest cities and airports to fly into, I want to share a quick tip to save money on airfare.

For the past 5 years, I’ve used Scott’s Cheap Flights (now called Going) to find cheap flight deals. It’s free and super easy to use. All you have to do is enter in your home airport (i.e. MKE or MWC) and where you want to go, and they’ll send you mistake fares and other ridiculously cheap flight deals.

In 2024 alone, I saved thousands of dollars thanks to their email alerts. This includes most recently, a $225 roundtrip fare from Miami to London. On average, I save about $300 roundtrip on selected flight routes. So, I’m a huge fan and couldn’t recommend them more!

If you’re a frequent flier, consider getting their premium version. It costs $49 per year, but it will easily save you hundreds (or thousands) of dollars if you fly just 1-2 times. I recommend signing up for the free trial (which you can cancel at any time) to test it out for yourself. And if you like it, use my coupon code JON20 to save 20%!

Top Cheap Flight Destinations from Milwaukee

Looking for cheap flight destinations from Milwaukee? Experience the vibrant culture of Madison, known for its scenic lakes and lively arts scene. Explore Omaha, home to historic districts, top-rated zoos, and Midwestern charm. Visit Green Bay for its waterfront beauty, outdoor adventures, and football heritage. Discover Grand Rapids, a city famous for its craft breweries, art museums, and riverfront attractions. Whether you’re after history, nature, or city life, these destinations offer budget-friendly escapes from Milwaukee.

Looking to save BIG on airfare? I recommend signing up for Dollar Flight Club. Thanks to DFC, I’ve saved $5,000+ on travel in 2024…so I couldn’t recommend it more!

1. Milwaukee to Madison ($77–$130 roundtrip)

• ✈️ Flight Time: 35 minutes
• 🛫 Airlines: Delta, United (via connections) (3+ daily flights)
• 📅 Best Time to Visit: June to September 🌞 and October 🍂 for fall colors
• 🏆 Perfect for: College town explorers 🎓, food enthusiasts 🧀, outdoor lovers 🚴

Madison is where lakeside beauty meets college town energy. This Wisconsin capital gives you incredible food, outdoor activities, and cultural attractions without needing to leave the state or break the bank.

The stunning State Capitol sits on an isthmus between two lakes, with its white dome visible from practically anywhere in the city. State Street connects the capitol to the University of Wisconsin campus with a pedestrian-friendly corridor packed with restaurants, shops, and bars that buzz with energy when students are in town. The five lakes surrounding the city provide endless recreation, with locals paddleboarding, sailing, and swimming in summer months.

When flying from Milwaukee to Madison, American Airlines occasionally offers direct options, while Delta and United connect via Chicago or Minneapolis. Summer brings perfect weather for enjoying Madison’s abundant lakes and outdoor patios, while October offers gorgeous fall colors reflecting in the water.

2. Milwaukee to Omaha ($81–$140 roundtrip)

• ✈️ Flight Time: 1 hour 30 minutes
• 🛫 Airlines: United, American, Delta (via connections) (4+ daily flights)
• 📅 Best Time to Visit: May to September 🌞 and June 🏆 for College World Series
• 🏆 Perfect for: Food enthusiasts 🥩, sports fans ⚾, budget travelers 💰

Omaha is where Midwestern friendliness meets unexpected sophistication. This Nebraska city delivers incredible steakhouses, a world-class zoo, and vibrant neighborhoods without the tourist crowds or high prices of larger destinations.

The Henry Doorly Zoo consistently ranks among America’s best with massive indoor rainforest and desert environments plus the largest indoor jungle in North America. Old Market district preserves historic brick streets and warehouses now filled with restaurants, galleries, and shops where you can watch glass blowers and artists at work. The food scene obviously centers around seriously amazing steaks. Omaha is home to some of the world’s largest meat processing facilities, meaning local steakhouses serve prime cuts at prices that would be doubled in bigger cities.

This route typically requires a connection through hubs like Chicago or Minneapolis. United through Chicago O’Hare usually offers the most options, though Delta through Minneapolis provides good alternatives with similar pricing. June is peak season with the College World Series taking over the city, while August and September bring perfect weather and fewer crowds.

3. Milwaukee to Green Bay ($41–$95 roundtrip)

• ✈️ Flight Time: 25 minutes
• 🛫 Airlines: Delta (regional service), United (via connections) (2+ daily flights)
• 📅 Best Time to Visit: June to September 🌞 and September to January 🏈 for Packers season
• 🏆 Perfect for: Football fanatics 🏈, outdoor enthusiasts 🎣, brewery hoppers 🍺

Green Bay is where small-town charm meets NFL legend status. This compact Wisconsin city gives you incredible football history, outdoor recreation, and authentic local culture without big city prices or pretension.

Lambeau Field is basically a football cathedral. Even if you’re not a Packers fan, the stadium tours and Hall of Fame are fascinating glimpses into sports history. Bay Beach amusement park offers ridiculously cheap family fun with rides costing just 25-50 cents each, while the adjacent wildlife sanctuary gives you miles of hiking trails through marshlands filled with birds and native plants.

When it comes to flights, Delta runs small regional jets, and midweek deals are your best bet especially between September and January when football season brings big crowds and higher weekend fares.

4. Milwaukee to Grand Rapids ($56–$115 roundtrip)

• ✈️ Flight Time: 50 minutes
• 🛫 Airlines: Delta, United (via connections) (3+ daily flights)
• 📅 Best Time to Visit: May to October 🍁 and September 🍺 for ArtPrize
• 🏆 Perfect for: Beer enthusiasts 🍺, art lovers 🎨, outdoor adventurers 🌲

Grand Rapids is where craft beer culture meets artistic innovation. This Michigan city delivers an incredible brewery scene, vibrant arts district, and easy access to Lake Michigan beaches without the crowds or prices of bigger destinations.

Beer City USA isn’t just a nickname. Grand Rapids boasts over 40 breweries within the metro area, with founders like Founders and New Holland leading a craft beer revolution that’s made this city a pilgrimage site for hop heads. Frederik Meijer Gardens & Sculpture Park combines stunning outdoor art installations with botanical gardens that change dramatically through the seasons. 

For the best experience, visit in late September or early October when crisp fall weather, vibrant foliage, and the city’s famous ArtPrize event turn the region into one giant outdoor gallery. Flights typically require a connection through Detroit or Chicago for this route.

5. Milwaukee to Fargo ($99–$160 roundtrip)

• ✈️ Flight Time: 1 hour 40 minutes
• 🛫 Airlines: Delta, United, American (via connections) (3+ daily flights)
• 📅 Best Time to Visit: June to September 🌞 and July to August 🌾 for festivals
• 🏆 Perfect for: Small city explorers 🏙️, craft beer lovers 🍺, budget travelers 💰

Fargo is where quirky Midwestern culture meets surprising urban coolness. This North Dakota city delivers incredible local dining, a booming craft brewery scene, and authentic prairie charm without tourist crowds or inflated prices.

Downtown Fargo has undergone a serious renaissance with historic buildings now housing trendy restaurants, boutique shops, and art galleries that showcase the region’s creativity. Broadway Square hosts outdoor concerts and events throughout summer, while the Plains Art Museum delivers exhibits that would impress in cities triple the size.

This route typically requires a connection through Minneapolis with Delta offering the most reliable service, though United through Chicago provides alternatives with similar pricing. Summer is absolutely the best time to visit with perfect weather and long daylight hours ideal for enjoying the many outdoor patios and events. 

6. Milwaukee to Dayton ($83–$140 roundtrip)

• ✈️ Flight Time: 1 hour 25 minutes
• 🛫 Airlines: American, United, Delta (via connections) (4+ daily flights)
• 📅 Best Time to Visit: April to October 🌞 and July 🛩️ for air shows
• 🏆 Perfect for: Aviation enthusiasts ✈️, history buffs 🏛️, brewery hoppers 🍺

Dayton is where aviation history meets Midwest authenticity. This Ohio city gives you incredible museums, emerging craft breweries, and genuine local culture without the tourist crowds or prices of nearby Columbus or Cincinnati.

The National Museum of the US Air Force is a must. It’s the largest military aviation museum in the world with over 350 aircraft and missiles, including actual presidential planes you can walk through. The Oregon District blends historic brick buildings with indie restaurants, cozy bars, and boutiques. History lovers will appreciate the deep ties to the Wright Brothers, from their original bicycle shop to Huffman Prairie, where they perfected early flight.

Flying from Milwaukee to Dayton typically requires a connection through hubs like Chicago or Detroit. United through Chicago O’Hare usually offers the most options, though Delta through Detroit provides good alternatives with similar pricing. Summer brings warm weather perfect for enjoying the city’s outdoor attractions and riverside paths along the Great Miami River. Every July, the spectacular Dayton Air Show attracts aviation enthusiasts from across the country with jaw-dropping aerial performances. 

7. Milwaukee to Sioux Falls ($102–$155 roundtrip)

• ✈️ Flight Time: 1 hour 30 minutes
• 🛫 Airlines: Delta, United, American (via connections) (3+ daily flights)
• 📅 Best Time to Visit: June to September 🌞 and July to August 🎭 for festivals
• 🏆 Perfect for: Outdoor enthusiasts 🏞️, small city explorers 🏙️, budget travelers 💰

Sioux Falls is where Great Plains beauty meets surprising urban charm. This South Dakota city delivers incredible outdoor adventures, unique local dining, and genuine Midwestern hospitality without tourist crowds or high prices.

Falls Park is the city’s crown jewel where the Big Sioux River cascades over pink quartzite formations right near downtown, illuminated by colored lights at night for amazing photos. Downtown has been completely revitalized in recent years with historic buildings, farm-to-table restaurants, and local shops selling everything from handmade jewelry to vintage vinyl. The outdoor opportunities here are endless. Good Earth State Park and the Big Sioux Recreation Area offer miles of trails through prairie landscapes dotted with wildlife, while the paved Sioux Falls Bike Trail loops nearly 30 miles around the city connecting major parks and attractions.

This route typically requires a connection through Minneapolis with Delta offering the most frequent service, though United through Chicago provides alternatives with similar pricing. Summer brings perfect weather and longer daylight hours ideal for enjoying the city’s many outdoor attractions and patios. 

8. Milwaukee to Memphis ($89–$145 roundtrip)

• ✈️ Flight Time: 2 hours
• 🛫 Airlines: Southwest, Delta, American, United (4+ daily flights)
• 📅 Best Time to Visit: April to June 🌸 and September to October 🍂 for pleasant weather
• 🏆 Perfect for: Music enthusiasts 🎵, BBQ lovers 🍖, history buffs 🏛️

Memphis is where music history meets incredible food culture. This Tennessee river city delivers legendary music venues, mind-blowing BBQ, and deep cultural history without the tourist markup of larger destinations.

Beale Street pulses with blues and jazz pouring from historic clubs where music legends got their start. Graceland lets you tour the surprisingly modest mansion where Elvis lived and died, filled with shag carpeting and other retro design choices that feel frozen in time. The food scene here revolves around BBQ that you will never forget.

Southwest offers some of the best direct flight options from Milwaukee with their generous baggage allowance, though they typically require booking further in advance for the best rates. Delta through Atlanta and American through Chicago provide alternatives with similar pricing. May brings perfect weather and the famous Memphis in May International Festival with its world championship BBQ cooking contest. October offers equally pleasant temperatures with smaller crowds and lower hotel rates. 

9. Milwaukee to Springfield ($90–$135 roundtrip)

• ✈️ Flight Time: 1 hour 10 minutes
• 🛫 Airlines: American, United (via connections) (3+ daily flights)
• 📅 Best Time to Visit: April to June 🌸 and September to October 🍂 for pleasant weather
• 🏆 Perfect for: History buffs 🏛️, Lincoln enthusiasts 🎩, architecture fans 🏠

Springfield is where American history meets small-city charm. This Illinois capital gives you incredible Lincoln heritage, beautiful historic architecture, and authentic Midwestern culture without tourist crowds or high prices.

Everything here revolves around Abraham Lincoln. The Lincoln Home National Historic Site preserves the only house he ever owned, while the stunning Abraham Lincoln Presidential Library and Museum uses cutting-edge exhibits to bring his story to life. Oak Ridge Cemetery houses his impressive tomb, where visitors often rub the nose on his bronze bust for good luck. Beyond the Lincoln sites, the spectacular Illinois State Capitol features a massive dome visible throughout the city, and the original Route 66 cuts right through downtown with retro diners and classic Americana vibes.

This route typically requires a connection through Chicago with United through O’Hare and American through Chicago offering the most reliable service. Visit in spring and fall to witness Springfield when it truly shines.

10. Milwaukee to Peoria ($74-$120 roundtrip)

• ✈️ Flight Time: 55 minutes
• 🛫 Airlines: United, American (via connections) (2+ daily flights)
• 📅 Best Time to Visit: May to October 🌞 and June to August 🎭 for festival season
• 🏆 Perfect for: River town explorers 🚢, architecture fans 🏛️, budget travelers 💰

Peoria is where riverfront charm meets surprising cultural depth. This Illinois city delivers historic architecture, vibrant arts scenes, and authentic Midwestern experiences without tourist crowds or inflated prices.

The revitalized Riverfront District offers gorgeous Illinois River views with walking paths, restaurants, and the interactive Peoria Riverfront Museum showcasing everything from art to science to regional history. The arts scene here punches way above its weight. The Contemporary Art Center houses working artist studios you can visit, while summer brings outdoor concerts at the CEFCU Center Stage with the river as a perfect backdrop.

This route almost always requires a connection through Chicago, with United offering the most consistent schedules through O’Hare. June through August brings the city to life with its iconic festivals, while October offers crisp weather and river bluff foliage at its peak.

11. Milwaukee to Fort Wayne ($113–$170 roundtrip)

• ✈️ Flight Time: 1 hour 15 minutes
• 🛫 Airlines: United, American, Delta (via connections) (3+ daily flights)
• 📅 Best Time to Visit: May to September 🌞 and June 🎵 for music festivals
• 🏆 Perfect for: Minor league sports fans ⚾, riverside explorers 🌊, budget travelers 💰

Fort Wayne is where Midwestern authenticity meets revitalized urban spaces. This Indiana city offers beautiful riverfront parks, excellent museums, and genuine local culture without tourist crowds or big city prices.

The Rivers define this city where three waterways converge, with the newly developed Promenade Park creating a stunning gathering space with pathways, event venues, and water features along the banks. Downtown has undergone a serious renaissance with historic buildings now housing breweries, farm-to-table restaurants, and unique shops around the beautifully restored Embassy Theatre. 

Flying from Milwaukee to Fort Wayne typically requires a connection through hubs like Chicago or Detroit. United through Chicago O’Hare usually offers the most options, though Delta through Detroit provides good alternatives with similar pricing. For the ideal time to visit, consider summer for the perfect weather.

12. Milwaukee to Tulsa ($145–$200 roundtrip)

• ✈️ Flight Time: 2 hours
• 🛫 Airlines: American, United, Delta (via connections) (4+ daily flights)
• 📅 Best Time to Visit: April to June 🌸 and September to October 🍂 for ideal weather
• 🏆 Perfect for: Art deco enthusiasts 🏙️, music history buffs 🎵, outdoor adventurers 🚣

Tulsa is where Midwest meets Southwest in the best possible way. This Oklahoma city delivers an incredible mix of cultural attractions, outdoor spaces, and food scenes that most travelers completely overlook.

The architecture here is seriously impressive. Downtown Tulsa is packed with perfectly preserved art deco buildings from the 1920s oil boom, giving parts of the city a Great Gatsby vibe you wouldn’t expect in Oklahoma. Gathering Place is a game-changer with its massive riverfront park, while the music heritage runs deep with the Woody Guthrie Center and newly opened Bob Dylan Center celebrating American legends.

This route typically requires a connection through hubs like Chicago, Dallas, or Denver. American through Dallas usually offers the most reliable service with the shortest layovers. May brings perfect spring weather with wildflowers blooming throughout the city’s many parks, while October offers gorgeous fall colors along the Arkansas River trails. 

13. Milwaukee to Wichita ($101–$160 roundtrip)

• ✈️ Flight Time: 1 hour 45 minutes
• 🛫 Airlines: American, United, Delta (via connections) (4+ daily flights)
• 📅 Best Time to Visit: April to June 🌸 and September to October 🍂 for pleasant weather
• 🏆 Perfect for: Aviation enthusiasts ✈️, art lovers 🎨, food explorers 🍔

Wichita is where plains hospitality meets surprising cultural depth. This Kansas city delivers incredible air and space attractions, vibrant arts districts, and authentic midwestern charm without tourist crowds or inflated prices.

Old Town has transformed from abandoned warehouses into the city’s coolest district with brick streets, local restaurants, and nightlife options housed in beautifully restored historic buildings. The Keeper of the Plains is a stunning 44-foot steel sculpture honoring Native American heritage, dramatically positioned at the confluence of two rivers with nightly fire displays. The aviation industry literally built this city, with Textron Aviation, Spirit AeroSystems, and Boeing all having major operations here. 

Flights typically require a connection through Chicago, Dallas, or Denver. American often offers the best combo of price and schedule through its Dallas hub. Visit in spring when wildflowers are blooming and festivals are in full swing.

• Read Next: Cheapest Places to Fly from Kansas City

Frequently Asked Questions (FAQs) About the Cheapest Flights from Milwaukee

Looking to expand your knowledge about the cheapest destinations from Milwaukee? Here are some common questions I get a lot about cheap flights from Milwaukee to anywhere.

What are the cheapest destinations from Milwaukee?

While this can change based on current promotions and seasons, some consistently cheap places to fly from Milwaukee include Madison, Omaha, Green Bay, and Grand Rapids, among others.

When is the best time to book cheap flights from MKE?

The best time varies based on your destination, but generally, booking 1-3 months in advance can yield great deals. Also, consider flying midweek or during off-peak seasons for your chosen destination.

Are there non-stop flights available for these cheap trips from Milwaukee?

Yes, many of the destinations on our listicle offer non-stop flights. Always double-check the flight details before booking.

Do fares change based on the day of the week?

Absolutely! Tuesdays and Wednesdays are often the cheapest days to fly, while weekends usually see higher prices.

Which airlines offer the best cheap flights from MWC?

Airlines like Southwest, Delta, and United frequently offer competitive fares from Milwaukee’s airports. But it’s always good to check smaller regional carriers or budget airlines that may have promotions.

Where is the cheapest place to fly from Milwaukee for international travel?

This can vary based on current flight deals, but often nearby international hubs like Toronto or Mexico City can be affordable options.

Do MKE and MWC offer the same flight deals?

Not always. While Milwaukee Mitchell International Airport (MKE) is the primary airport and has more flight options, General Mitchell International (MWC) might offer specific regional deals. Always check both when searching!

Is it cheaper to book a round trip or two one-way tickets?

It depends. Sometimes booking two one-way tickets, potentially with different airlines, can be cheaper, but round-trip fares often come with their own discounts.

How can I stay updated on the cheapest flights from Milwaukee to anywhere?

Signing up for airline newsletters, using fare alert tools, or joining frequent flyer programs can keep you in the loop for the latest deals.

Do last-minute flights offer better deals?

Occasionally, airlines offer last-minute deals to fill empty seats, but this is becoming less common. It’s generally more cost-effective to book in advance when you’re flying from Milwaukee. I always recommend saving your money on luxury accommodations and instead spending it on flights.