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Published on May 31, 2019
Festival travel: Travel from Orlando to Milwaukee for SummerfestPhoto: iStock

Wisconsin winters can be brutal, which means locals know how to enjoy the summer. The annual Summerfest in Milwaukee is one of the largest and most affordable music festivals in the U.S., and it's happening June 26 to July 7, so there's just enough time to start making travel plans.

The city's Summerfest grounds include more than 10 stages, plus an interactive sports zone and a children's theater and play zone. The venue is located downtown on the Lake Michigan waterfront, near many of the city's famous breweries, as well as restaurants, theaters, galleries and more.

Using travel site Skyscanner, we’ve sifted through the cheapest flights between Orlando and Milwaukee, including some standout hotel options and other favorite local attractions. (Prices and availability are current as of publication and subject to change.)

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Cheapest Milwaukee flights

The cheapest flights between Orlando and Milwaukee are for departure on June 28 and return from Wisconsin on July 5. Allegiant Air currently has roundtrip tickets for $192.

If you fly out of Orlando on June 28 and return from Milwaukee on July 1, Frontier Airlines can get you there and back for $203 roundtrip.

Top Milwaukee accommodations

Regarding where to stay, here are two of Milwaukee’s top-rated hotels, that we selected from Skyscanner's listings based on price and customer satisfaction.

The Pfister Hotel (424 E. Wisconsin Ave.)

Photo: Trip by Skyscanner

For an all-around top recommendation, consider the Pfister Hotel. The hotel has a 4.6-star rating on Skyscanner, and rooms are currently available for $169.

Set in the heart of Milwaukee, this hotel is close to the Marcus Center for the Performing Arts, the Milwaukee Art Museum and Discovery World. 

The InterContinental Milwaukee (139 E. Kilbourn Ave.)

Photo: Trip by Skyscanner

Another option is The InterContinental Milwaukee. The 4.4-star hotel has rooms for $126/night. It's close to the Pabst Theater and Milwaukee City Hall. 

Featured Milwaukee restaurants

If you're looking for a popular spot to grab a bite, Milwaukee has plenty of excellent eateries to choose from. Here are a few from Skyscanner's listings to help you get started.

Leon's Frozen Custard (3131 S. 27th St.)

Photo: Trip by Skyscanner

Let's start with a Dairy State essential: ice cream. For a popular option, check out Leon's Frozen Custard, which has an average of five stars out of 13 reviews on Skyscanner. A Milwaukee mainstay for more than 75 years, it's still owned and operated by the original family.

"This institution is open all year, and they are open late into the night, at least during the summer," wrote visitor Steve. 

Milwaukee Public Market (400 N. Water St.)

Also worth considering is The Milwaukee Public Market, with a variety of artisan and ethnic products and freshly made prepared foods. Dine in the market’s second-floor Palm Garden. The market also offers cooking classes.

"Large indoor market with a wide array of vendors. Great for a casual, pickup lunch or dinner," wrote visitor Lizzie. 

Cafe Corazon (3129 N. Bremen St.)

Photo: Trip by Skyscanner

Finally, there's Cafe Corazon. The Mexican restaurant supports local farmers and raises its own beef and produce. Its desserts are based on seasonal ingredients.

"Cafe Corazon has delicious Mexican food. The place has character and nice drinks," wrote visitor Anya.

Top Milwaukee attractions

Not sure what to do in Milwaukee, besides eat and drink? Here are a couple of recommendations, provided by Skyscanner.

The Milwaukee Art Museum (700 N. Art Museum Drive)

Photo: Trip by Skyscanner

First up is The Milwaukee Art Museum, with four floors of rotating displays and over 30,000 works of art. The recently expanded museum dates back to the 1880s and encompasses many types of art forms.  

"Artists featured in the museum include Winslow Homer, Auguste Rodin, Edgar Degas, Claude Monet, Henri de Toulouse-Lautrec, Pablo Picasso, Joan Mir ó and Andy Warhol," wrote visitor Mary. 

Harley-Davidson Museum (400 W. Canal St.)

Photo: Trip by Skyscanner

You can also rev up your visit at the Harley-Davidson Museum. This museum celebrates the more than 100-year history of Harley-Davidson motorcycles.

"This museum is a must-see for motorcycle buffs. On display one will find more than 450 motorcycles and artifacts, dating back to Serial Number One, which is the oldest-known Harley-Davidson motorcycle," wrote visitor Mary. 


This story was created automatically using flight, hotel, and local attractions data, then reviewed by an editor. Click here for more about what we're doing. Got thoughts? Go here to share your feedback.