There are few better ways to start a weekend in the city than with an Chicago Greeter (chicagogreeter.com) tour. The free—yes, you read that right—walks feature friendly guides with knowledge that will surprise even native Chicagoans. Register in advance for a customized tour (such as art and architecture, food or local history) or just show up on the spot for for a one-hour guided tour of downtown.
Photo courtesy of Choose Chicago and Chicago Greeter
Settle in with for your first day's lunch at The Gage (thegagechicago.com). This gastropub feels fancy but is easy on the budget. We recommend the Regular Burger, for the perfect combination of juicy meat, melted cheddar, and a perfectly toasted bun.
Then make your way down to The Magnificent Mile (themagnificentmile.com), where more than 450 stores and boutiques provide hours of shopping and people-watching.
The Millennium Knickerbocker Tour (millenniumhotels.com) takes guests through Chicago’s infamous Millennium Knickerbocker hotel, with tales of secret staircases, Al Capone’s penthouse speakeasy, and wild times under the ownership of Hugh Hefner. Tours, which are available even to non-guests, begin in the hotel lobby at 3 pm on Fridays and Saturdays.
Located along the Magnificent Mile, The Purple Pig (thepurplepigchicago.com) is a great place to grab a bite to eat before a night out. The James Beard Award-winning chef composes a menu of adventurous gourmet dishes starring, you guessed it, pork. The Purple Pig’s small, tapas-like plates are perfect for sharing.
Hamilton might be the musical on everyone’s minds, but mix it up with a show at the Chicago Shakespeare Theater (chicagoshakes.com). This beautifully designed venue on Navy Pier makes the Bard’s classics accessible for all. Showing this summer: Shakespeare in Love. (If Shakespeare's not your thing, check out Hot Tix (hottix.org) for last-minute, half-price tickets to direct-from-Broadway shows and other productions.)
Take the short taxi ride back to the Renaissance Blackstone Chicago (marriott.com) to rest up with great views of Lake Michigan.
Following breakfast at the hotel, walk to the Adler Planetarium (adlerplanetarium.org) for Sun Salutations Yoga. Find your zen out among the stars at this yoga session under the dome, as relaxing narrations point out constellations. Be sure and reserve your tickets well in advance, though—this hot event sells out fast. After, spend some time browsing Adler's exhibits and shows—the new Changing Eclipses exhibit immerses you in a mock solar eclipse before we experience the real thing in August.
Photo courtesy of David Miller/Adler Planetarium
Next, refuel at 3 Arts Club Café (3artsclubcafe.com), a sophisticated dining experience complete with an indoor courtyard. Comfy couches surrounded by olive trees and bathed in natural light—thanks to the glass ceiling atrium above—turn the ambiance from good to great. Gather around the delice de Bourgogne cheese board for a sophisticated mid-day pick-me-up.
Just a short distance away lies Lincoln Park Zoo (lpzoo.org), Chicago’s famous free, year-round zoo. Spend a couple of hours among the polar bears, snow monkeys and red pandas—and don’t forget to visit the zoo’s newly hatched Chilean Flamingos.
Snow monkey photo courtesy of the Lincoln Park Zoo
Round out the afternoon at the Museum of Contemporary Art (mcachicago.org), where diverse exhibits ensure every trip is an adventure. Right now, check out Riot Grrrls—a celebration of bold female artists and their works—and Chicago Works: CHRIS BRADLEY—where everyday objects like potato chips and pizza boxes are not as they seem.
GT Fish and Oyster (gtoyster.com), in River North, is the last stop on your Chicago getaway. Enjoy fresh seafood and attentive service, and round out your Chicago stay with a slice of decadent chocolate caramel devil’s food cake.