Best Rooftop Scene for Those Who Don’t Want a Scene

Between the rumblings of L trains passing nearby and the vibrations from bands playing downstairs, this fourth-floor South Loop rooftop isn’t for the faint-hearted. But what it lacks in refinement, Reggies Trainwreck Rooftop Deck — actual name — more than makes up for in unpretentious charm. Grab a spot at the bar, where friendly bartenders can walk you through … Read more

Best Brewery for Beer Nerds

For people who love European-style offerings — from hefeweizens and Kölsches to smoky Grodziskies — Dovetail Brewery in North Center is heaven. Its relaxed vibe makes it approachable for imbibers of all types, but beer geeks can buckle down and sip through spontaneously fermented beers like fruity krieks, framboises, and funky bourbon-barrel-aged gueuzes while affable bartenders school you in … Read more

Best Sports Bar That Doesn’t Act Like a Sports Bar

Over my 30 years as a sportswriter, sports bars have always left me wanting more — even in places where I’ve become the Black Norm. That’s until I visited Signature in the South Loop. It’s from former Chicago Bear Israel Idonije and chef Stephen Gillanders, who met in 2018 when Idonije dined at Gillanders’s S.K.Y. The ambience … Read more

Best Designer for Dressing You Like Michelle Obama

Say you are in town for a certain convention and have long admired the stylish fits of a certain former first lady. It’s time to get acquainted with Maria Pinto (that’s her, pictured above), Michelle O’s go-to designer throughout her husband’s presidential run (who can ever forget that ocean-blue 2008 DNC dress?). Pinto’s designs aren’t … Read more

Best Spot for Classy Chicago Souvenirs

When I wanted Chicago-centric gifts for relatives in Germany, I knew where to shop — and it sure wasn’t on Navy Pier for Windy City shot glasses. No, I went to the Chicago Architecture Center’s Design Store. Amid books, games, and prints, you’ll find the likes of Frank Lloyd Wright–inspired earrings and tea towels featuring a modernist … Read more

Best Place to Pretend You’re Shopping in Paris, Not Edgewater

POV: You’re strolling down Broadway when you spot a petite corner shop exuding an unmistakable je ne sais quoi. Marais, says the front, after the historic district in Paris. You enter an airy space, punctuated by the scent of fig and earth. Songstress Carla Bruni croons through speakers en français as you peruse the paper … Read more