Carrie Garcia / Alamy

This sizable North Side neighborhood boasts Boystown, baseball, and everything between.

Travel + Leisure

One of Chicago’s largest neighborhoods, Lakeview offers a wide range of diversions. Home to Wrigley Field, Wrigleyville welcomes Cub fans on game day. Baseball banter and bars are plentiful here. Go to Boystown, home to the city’s largest LGBT community, to experience great restaurants, unique shops, and dance clubs. On Broadway and Clark, you’ll find record shops, thrift stores, cafés, and a variety of restaurants. Head to Southport for boutiques and upscale restaurants. And on Lincoln, you’ll come across more good places to dine and great music venues. Off the main streets, walk along Pine Grove between Diversey Parkway and Surf, and you’ll pass Brewster Building, once home to Charlie Chaplin and whose interior was used in the horror film Child’s Play. Finally, jutting up from Addison and Lake Shore is the 40-foot Kwanusila Totem Pole, anchoring this large, entertaining North Side neighborhood.

Southport Grocery & Café

Leaving her job as a CPA to go to culinary school led Lisa Santos to open this half café, half specialty grocery store in Lakeview back in 2003. The café’s narrow layout means most of the seating is against the wall adjacent to the open kitchen, affording patrons excellent views of the culinary action. Hardwood floors, comfortable banquets, and large white lanterns also enhance the space, although many prefer the shaded patio during summertime. The modern American menu is most admired for breakfast favorites like the subtly sweet cupcake pancakes topped with vanilla sugar butter.

Music Box Theatre

In Lakeview off Southport Avenue, bright red lights illuminate the sign above an old-fashioned marquee at this retro theater. Completed in 1929 when movie palaces were popping up all around downtown Chicago, the Music Box Theatre is now considered the best theater in the city for foreign and independent films and has also hosted such notable premieres as Gone Baby Gone. The main 800-seat auditorium retains original features like the enormous columns, dramatic red curtain, and cove-lit ceiling, which resembles a night sky with twinkling stars and moving clouds. Monthly silent movie screenings are accompanied by the theater organ.

Crisp

In the land of 20-pound pizza and street-seller hot dogs, there’s a new craving in town, and it comes from (and with) Seoul. Crisp, a Korean fried chicken headliner in the Lakeview ‘hood, dishes out a half dozen versions of chicken, all served two ways: half or whole. For Sassy Seoul, the cooks bathe the birds in a garlic-ginger-soy blend, dust them with flour, then double-fry for a mysteriously greaseless finish. The Plain Jane has a golden, almost translucent coating, the trademark of the Korean fried chicken tradition.

Flub A Dub Chub’s

Tucked below a psychic shop, Flub A Dub Chub’s is the choice for anyone hankering for dogs, burgers, or hot beefs. Though it’s branded a hot dog emporium, the Roe burger (a burger topped with bacon, avocado, and cheddar) was voted one of the best in the city.

Schubas Tavern

A Lakeview institution, Schubas Tavern has featured nightly live music for more than 20 years. The building itself, constructed by the Schlitz Brewery more than 100 years ago, is a Chicago Historic Landmark, and on the exterior two old Schlitz globe logos are still visible. The interior features a beautifully refurbished mahogany bar, tin ceiling, and walnut wainscoting. Check the website for upcoming music shows.

Wrigley Field Tour

Wrigleyville is the primary destination for many travelers to Chicago. Cubs fans flock to Wrigley Field on game day despite their beloved team’s infamous defeats. Experience the Cubbies’ home field up close in the daily tours offered at Wrigley.

Chicago Music Exchange

In a neighborhood dotted with music venues, this instrument shop fits right in. Even if you’re not in the market for a vintage Fender, the sheer number of guitars in this place is remarkable, making it seem more a museum than a store. Enjoy live music, in front of the Wall of Gibsons, where there’s a performance space for local and touring musicians.

Tula

Owned by a mother and daughter team, Tula sells a well-edited collection of European and contemporary designs in a charming vintage brownstone. Find the perfect open back sweater, linen scarf, and beaded clutch in this welcoming boutique.

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