So, you want to be a Chicagoan. If you want to feel what it’s like to experience the Windy City like a native, read on. Step one: avoid Michigan Avenue. Yes, it’s a lovely street, but the department and chain stores are magnets for large throngs of sightseers, not locals. Step two: take public transportation. The best way to feel a part of a city is to hop on the bus, or, in our case, the EL, and navigate the route from point A to B. You’ll rub shoulders with the most fascinating cast of characters, and get to see off-the-beaten path scenery. Step three: enjoy nature in a celebrated park. Take a low-key walk to experience the local flora, fauna, and average folks just going about their day. Step four: find an authentic activity—listening to music, cheering on the home team, shopping at a local market, or drinking at a neighborhood watering hole—so you can experience the third coast through a local’s eyes.
The Green Mill
It's a hike, but Green Mill's status as one of the oldest jazz clubs in the country (opened in 1907), with well-documented visits from Charlie Chaplin and Gloria Swanson, make this trek to Al Capone’s former speakeasy more like a pilgrimage. Locals revel in the old-school ambiance as much as the standout jazz.
Green City Market
Every Saturday, locavore-loving foodies and A-list chefs like Stephanie Izard descend on Green City Market—coffee in hand—to snap up the freshest produce, cheeses, and baked goods before kicking back on the grassy meadow, custom crepe in hand. The market moves to Peggy Notebaert Nature Museum during winter months.
Tracking down that authentically cool, off-the-grid restaurant can be tricky. Make like a local and head to West Town where a former fireplace mantle factory turned neighborhood boite beckons with craft-oriented cuisine and killer cocktails. The Dawson is a perfect hybrid of urban verve and chill ambiance.
Randolph Street Market
Browsing flea markets for vintage treasures is a decidedly non-tourist activity. This celebrated European-style antique market features 250 vendors hawking quality vintage clothing, jewelry, furnishings, and home décor. Shoppers are revived with on-site entertainment and food trucks. Valet parking makes the experience seamless.
Lincoln Park Zoo Nature Walk
To experience the true definition of “urban oasis,” stroll in and around this 14-acre ecosystem with the backdrop of the Chicago skyline. Connected to Lincoln Park Zoo, the nature boardwalk crisscrosses a large pond which serves as an ecological habitat teeming with turtles, fish, frogs, and birds. Prairie grass surrounds the perimeter.