In a prime location among Chicago’s award-winning restaurants, platinum shopping, and inspiring architecture, you’ll find the hip Virgin Hotel, the first property in Sir Richard Branson’s hotel line. Its concierge, Chad Edwards, is the man in the know to get the best out of your time in the Second City.
Best new restaurant: The Dearborn
One of my personal favorites is the Dearborn. It’s modern yet kind of classic, like my mom’s taste mixed with a minimalist’s Pinterest board: old tiles, industrial light fixtures. The white bean hummus on its meze plate and the bone-in filet mignon are my go-tos. 145 N Dearborn St, Chicago, IL 60602. (312) 384-1242
Exclusive reservation: Girl & the Goat
Outside of a ticketed dinner like Alinea, the hardest table to grab is at Girl & the Goat. It has been open for a few years, but the demand is as high as ever because of chef Stephanie Izard’s reputation for quality food. No one I know has ever had anything bad to say about it. 809 W Randolph St, Chicago, IL 60607. (312) 492-6262
Emerging neighborhood: Logan Square
Every time I’m in Logan Square, I find new places popping up. There’s a cozy redone movie theater and tons of little galleries, like Galerie F, which I love, and that’s right across the street from East Room, one of my favorite new places for live music in Chicago.
Related: How to Have a Spectacular Day in Chicago
Cocktail spot: The Violet Hour
The bartenders are very nice and patient at the Violet Hour, a bar that looks like nothing from the outside but inside is intimate and chic, and in a welcoming way. The drink menu is so long, I usually just wind up talking to whoever is behind the bar about what I’m in the mood for, and he comes up with something great and different every time. 1520 N Damen Ave, Chicago, IL 60622. (773) 252-1500
Under-the-radar museum: The Museum of Contemporary Art
The Museum of Contemporary Art lives in the shadow of the Art Institute, but it’s just as world-class. The MCA’s collection changes up every few months, so it feels like it’s a whole new museum every time I’m there. 220 East Chicago Ave., Chicago, IL 60611. (312) 280-2660
Shopping spree: Kokorokoko
On Milwaukee Avenue between Division and Damen in Wicker Park, where lots of independent boutiques have opened recently, Kokorokoko is a great vintage shop stocked with ’90s throwback stuff like ALF trading cards and New Kids on the Block tapes. 1323 N Milwaukee Ave, Chicago, IL 60622. (773) 252-6996
River activity: Architectural boat tour
The architectural boat tour on the Chicago River is one of the most touristy, popular things to do in Chicago, but it’s popular for a reason. I do it every year and take friends. Chicago Line and First Lady consistently do the best job.
The deep-dish dish: Lou Malnati's
In Chicago, you either like Lou Malnati’s or Giordano’s for pizza; it’s like the White Sox or the Cubs. I’m partial to Lou’s for the flavor of the sauce. I always recommend the Gold Coast location.
A version of this article appears in the March 15, 2017 issue of Fortune with the headline "The City of Broad Shoulders." We’ve included affiliate links in this article. Click here to learn what those are.
