Clark Street Pub Crawl

Once a Native American trail, Clark Street is one of Chicago's major arteries, running roughly 12 mi from Chinatown on the South Side to the border with Evanston at the north. A Clark Street pub crawl, with stops in three distinct neighborhoods, gives you a taste of this vibrant, diverse city that plays as hard as it works.

Downtown/River North

Begin your pub crawl where Clark Street meets the Chicago River. From the Clark Street Bridge, the city spreads out in all directions. On your left are the iconic corncob structures of Marina Towers, with Lake Michigan in the far distance, and a series of bridges spans the river on both sides.

If you're kicking off your walk during the day, to Fado (100 W. Grand Ave. 312/836-0066), an ornate Irish pub featuring decor imported from the Emerald Isle. Relax with a perfectly poured pint of Guinness and a hearty boxty. Blues fans should check the night's lineup at Blue Chicago next door to see whether it's worth heading back downtown for music and a nightcap. If you're starting after 5 pm, go straight to Swirl Wine Bar (111 W. Hubbard St. 312/828-9000). Look carefully as the tiny storefront entrance is easy to miss. Grab a spot on a plush sofa or the curving banquette in the cozy, dimly lit lounge. After imbibing a glass or two and sharing a pizza or antipasto plate, take a five-minute walk to the Grand Avenue Red Line station, where you'll hop on a northbound El train. You can also flag a cab or grab a northbound bus on Dearborn.

Lakeview/Wrigleyville

Exit the Red Line at Addison and walk to Murphy's Bleachers (3655 N. Sheffield Ave. 773/281-5356), directly across from Wrigley Field's bleacher entrance. The historic sports bar's rooftop is the best place to watch a Cubs game outside of the Friendly Confines. With sports memorabilia lining the walls and numerous brews on tap, it's the quintessential Wrigleyville experience. Goose Island Wrigleyville (3535 N. Clark St. 773/832-9040) is a brewery/sports bar pays homage to two local passions: beer and baseball, though it's less Cubs-centric than Murphy's. Finish getting your sports fix and head back to the Red Line stop at Addison.

Andersonville

Exit the Red Line at Berwin and whet your thirst with a stroll through Andersonville. Beer aficionados flock to The Hopleaf (5148 N. Clark St. 773/334-9851) for its mind-boggling selection of international drafts and bottled beers. Note that the bar area gets very crowded on weekends and there's almost always a wait for a table. Energy flagging by this point? Luckily it's just quick stumble north to your last stop, Simon's Tavern (5201 N. Clark St. 773/878-0894). Look for the neon sign depicting a fish hoisting a martini—a play on "pickled herring." This slightly divey bar is steeped in local history. The original owner, a bootlegger during Prohibition, used to cash paychecks in a bulletproof booth on the premises. When you're ready to call it a night, hail a cab or hike it back to the 24-hour Red Line.