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Minneapolis, MN
Miles from Chicago 410

Why you should go To catch shows at music venues such as Triple Rock Social Club and CC Club, a punk dive where the Replacements used to hang out. “Be sure to grab a Grain Belt Premium beer while you’re in town; it’s got a unique sweet bite to it—it’ll grow on you,” says TOC associate art director Mike Novak (who considers the Twin Cities area his second home).
When to go July 17–25, for the city’s Best Days of Summer Aquatennial (a citywide summer fest celebrating its 70th year), which includes a parade, boat races, a sand-castle-building competition and a fireworks display (

Cincinnati, OH
Miles from Chicago about 300

Why you should go “Most of the year, Cincinnati’s skyline is a view only a son-of-the-city could love. But every Labor Day weekend it gets lit up with fireworks when WEBN (the closest thing you’ll get to WKRP) puts on its annual Riverfest. Set to music, the fireworks color the sky right over the Ohio River, and it’s so fantastic it even makes Kentucky look good,” according to TOC associate features editor (and Cincy native) David Tamarkin.
When to go In addition to Labor Day, June 20 and 21 offers the family-friendly Juneteenth Festival in Eden Park, which celebrates the end of slavery with historical presentations, drum-line presentations and food. Or, if you’re more of a beer fan, visit the weekend of September 19, when five blocks of downtown Cincy are transformed into Oktoberfest Zinzinnati, one of the nation’s largest Oktoberfests.

Milwaukee, WI
Miles from Chicago 74

Why you should go “A Brewers game at Miller Park is a great excuse to tailgate with some beer and brats in the parking lot. Coming from a Cubs fan, the stadium is truly a sight to be seen and enjoyed in the sun or rain—thanks to the retractable roof,” says Amy Burkhardt, former Chicagoan and recent Milwaukee transplant.
When to go Anytime between June 25 and July 5 for the huge, multiday Summerfest, which is touted as “the world’s largest music festival” and this year features headlining acts such as Bon Jovi, No Doubt, Bob Dylan, Stevie Wonder and Kenny Chesney.

Iowa City, IA
Miles from Chicago 218

Why you should go “Iowa City completely transforms in the summer—from an underage drinker’s haven during the school year to a laid-back bohemian town,” says TOC partnership coordinator (and University of Iowa alum) Kate Lowery. “Start at Prairie Lights bookshop and take a seat in the ped mall for some shady reading and Hackey Sack watching. Window shop around downtown and walk over to Linn Street to grab some lunch at the famous Hamburg Inn—the vegetarian BLT is my fave.”
When to go July 3–5, for the Iowa City Jazz Festival, where more than 50,000 attendees show up for free music in downtown Iowa City.

Indianapolis, IN
Miles from Chicago 189

Why you should go “Visit the Indy 500 track—there’s a museum and they give you a lap around. And for the hottest shrimp-cocktail sauce ever, make sure to stop by St. Elmo’s Steak House,” says TOC advertising account manager (and Indy native) Mari Taisch.
When to go Saturday 13 and Sunday 14, for the Talbot Street Art Fair, a free event where you can browse and purchase works by local and international artists.

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