Chicago, City of Big Shoulders, has a vibrant cultural scene and the sights, sounds and tastes to match. Short on time? No reason to sing the blues: You can blow into the Windy City for just 24 hours, live it up to the hilt, and then savor it on the plane, car or “El” ride home:
Breakfast – Chicago Diner
Start the day with a namesake – folks scramble for the breakfast bowl, cinnamon rolls, and even carnivores rave about the vegetarian and vegan options. No matter what time of day, patrons say you should act like a kid again and get the peanut butter milkshake!
Coffee – Intelligentsia Coffee Roasters
These hometown coffee roasters take their brewing seriously. Don’t expect to have your order delivered within seconds–but rather, enjoy the spectacle of the brewing process: each cup is brewed individually and meticulously timed–it’s an art form, really, and well worth the wait!
Tip: If the line is long in the morning, “go down the stairs in the building next door and grab your coffee in the pedway.”
Lunch – Manny’s Deli
Yes, you can “hang with the politicos”—Obama’s campaign team practically made this place their cafeteria–but let your stomach and taste buds vote: corned beef, onion rolls, matzo ball soup and potato pancakes are what diners wax poetic about, but some think the turkey pastrami is an “unsung hero.”
Dinner – Pizano’s Pizza
Deep dish, stuffed, thin crust—there’s great debate as to who does it best. Even Oprah’s weighed in on the issue, declaring 60-years-old-and-counting Pizano’s her favorite.
Patrons suggest starting off with the “very fresh” bruschetta, washed down with “great martinis” or Guinness on tap; for toppings, the vegetarian or “vegetarian plus pepperoni”; thin crust, deep dish and butter crust choices are all winners.
If you’ve got room, top it all off with the skillet chocolate chip cookie, baked in a cast iron pan, served warm with ice cream, hot fudge, and whipped cream.
Get Out – Millennium Park
Chicago is world-renowned for its architecture, and Millennium Park is the convergence of architecture, sculpture, and landscape design. You’ll find an amazing array of concerts, exhibitions, tours, and family activities. The park is actually a green roof: 24.5 acres built on top of a subterranean parking garage.
Tip: Get your photo taken in front of Cloud Gate (a.k.a. “The Bean”), a kidney-shaped sculpture with a 12-foot arch.
Get Cultured – Art Institute
Well, you’ve hit it, the mother lode, rivaling any world-class museum on the other coasts and beyond. Perhaps most famous for its outsize Impressionist and Post-Impressionist collection, you’ll also find American Masters like Edward Hopper, Jackson Pollock and Georgia O’Keeffe (who spent her formative years in neighboring Wisconsin). Don’t overlook the armor collection and modern wing as you ponder Pointillism.
Tip: Ride the escalator from Millennium Park to the museum’s roof cafe. The “views of the ‘mile’ are magnificent.”
Nightlife – The Green Mill Cocktail Lounge
After dark, wind down and soak up the vibes at The Green Mill. Dating from 1907, this former speakeasy and mobster hangout is full of history: Al Jolson headlined, and one of Al Capone’s henchmen had part ownership of the club in the 1920’s. There’s also a trap door and escape tunnel (if you’d ever need it). From jazz to Open Mic to the “original” poetry slam this joint is jumpin’ every night.
Tip: Order a “superb” vodka martini, extra dirty, or a Long Island iced tea.