Bay Area/ San Jose

Festival travel: Escape from San Jose to Milwaukee for Summerfest

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Published on May 31, 2019
Festival travel: Escape from San Jose 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 United States, and this year it's happening from 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, a children's theater and a play zone. The venue is located downtown on the Lake Michigan lakefront, 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 San Jose and Milwaukee, including some popular hotel options and other highly reviewed local attractions. (Prices and availability are current as of publication and subject to change.)

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Flight deals to Milwaukee

Currently, the cheapest flights between San Jose and Milwaukee are if you leave on June 27 and return from Wisconsin on July 1. Delta currently has round-trip tickets for $512.

Top Milwaukee accommodations

To plan your stay, here are two of Milwaukee’s top-rated hotels, according to Skyscanner, that we selected based on price, proximity to things to do 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. With a 4.4-star rating on Skyscanner, the hotel is one of the most luxurious in the city. Rooms are currently listed for $126/night.

This hotel is close to Pabst Theater and Milwaukee City Hall.

Featured Milwaukee food and drink

Milwaukee has plenty of top-notch dining options. Here are a few of the most popular, according to Skyscanner.

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

Photo: Trip by Skyscanner

First things first: dessert. For a popular option, check out Leon's Frozen Custard, which has an average of five stars out of 13 reviews on Skyscanner.

Leon's Frozen Custard opened for business on May 1, 1942. The business is 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. 

Beans & Barley Market, Deli & Cafe (1901 E. North Ave.)

Photo: Trip by Skyscanner

If you're looking for a local favorite restaurant pick, head to Beans & Barley Market, Deli & Cafe, with 4.9 stars from 10 reviews.

"Everything about this restaurant and co-op is comforting and delicious," wrote reviewer Andrea. "On the co-op side of the building, you can pick up everything from books and magazines to grocery and sundries. The menu items on the restaurant side include local and delicious vegan, vegetarian and meat items."

Cafe Corazon (3129 N. Bremen St.)

Finally, there's Cafe Corazon.

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

Top Milwaukee attractions

To round out your trip, Milwaukee offers plenty of popular attractions worth visiting. Here are a couple of top recommendations, based on Skyscanner's descriptions and reviews.

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

Photo: Trip by Skyscanner

First up is The Milwaukee Art Museum.

The Milwaukee Art Museum is a perfect place for art lovers young and old. With four floors of rotating displays and over 30,000 works of art, there is truly something for everyone. 

"This museum has been expanded and renovated recently to a current size of 341,000 square feet," wrote visitor Mary. "This collection includes European art from the 15th through the 20th century as well as American art from the 17th to 20th century."

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

Photo: Trip by Skyscanner

Lastly, spend some time at Harley-Davidson Museum.

This museum celebrates the 100-plus-year history of Harley-Davidson motorcycles with trivia, models and exhibits.

"This museum is a must-see for motorcycle buffs," wrote visitor Mary. "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."


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.