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Chicago Summer Extravaganza!

Chicago Summer Extravaganza!

Trip Plan Tags: 
day trip
North America,
United States

I haven't done a typical touristy Chicago summer yet... Jason will you join me?



Bucktown/Wicker Park

More than ten years after first being "discovered" by bohos and style-makers, the neighborhood has earned its high-hip status with the city's most exuberant boutiques, galleries, cafés, and indie-rock bars. The area is a couple miles northwest of the Loop and is anchored by the intersection of North, Damen, and Milwaukee avenues.

Begin at Hejfina, where the smartly edited collection veers from men's and women's labels (most popular: Acne Jeans from Sweden) to exhibitions by local artists to pared-down furniture. Intent on outfitting your inner outlaw, Bonnie and Clyde's is the only Chicago boutique to feature Project Runway winner Jeffrey Sebelia's Cosa Nostra line. But it's the very witty Vlieger & Vandam bags (one purse comes printed with the entire skeletal X-ray of a small dog) that put the shop on the edgy map.

Stop in at the neighboring Hot Chocolate for cakes, shakes, and warm brioche donuts—or just grab some sandwich cookies from the takeout counter. Then head to Apartment Number 9 for menswear by Dries Van Noten, Etro, and Paul Smith. P. 45 has innovative, global women's labels (Phillip Lim, Ulla Johnson, Michelle Mason), plus some local jewelry designers you've never heard of—yet. Stitch is crowded with glazed Tampopo tableware, Votivo candles, and striped, jewel-toned Missoni wool throws.

For more of a patina, try Pagoda Red, where beaming Buddhas and antique yet eminently modern-looking Chinese chests, coffers, and chairs stand ready to furnish your loft. At Reckless Records, the tireless staff will help you sift through vinyl and rare box sets of jazz, soul, and, of course, indie recordings. End up at Trillium, where the haul (primarily women's fashions from brands like Joie, Cynthia Vincent, and Vince, plus J.W. Hulme bags) showcases preppy classics with a tomboy subtext.—Updated by Raphael Kadushin


Second City, Illinois

1616 N. Wells Street
Chicago, Illinois 60614
Tel: 312 337 3992

If you only go to one comedy club in your life, this should be it. Yes, you'll find Second City franchises scattered about the country, but there's no matching the original. A perusal of the framed photos in the foyer is a who's who of funny: Dan Aykroyd, Gilda Radner, John Candy, Steve Carrell, Stephen Colbert, Mike Meyers, and Amy Sedaris are just some of the comedians who started their careers here. The casual main theater—officially called "The Second City Mainstage"—seats 290 and is as classic as comedy clubs get; you'll likely be seated randomly at a table and plied with drinks and appetizers until the show begins. Big names and alums still perform here periodically, but both the Mainstage and Second City e.t.c. (a smaller, second stage) have resident troupes that write and perform original comedy revues.

Performance times vary; call ahead.


Billy Goat Tavern, Illinois

430 N. Michigan Avenue
Chicago, Illinois 60611
Tel: 312 222 1525

The classic Saturday Night Live skit where native Chicagoan John Belushi played a harried Greek line cook—shouting, "Cheezborger, cheezborger, cheezborger. No Pepsi. Coke!"—brought this Chicago institution (which the skit was based on) to national fame in the late '70's. But it's been a local landmark since its original owner, William Sianis, was forbidden by the Chicago Cubs management from bringing his house goat—yes, a real live goat—to Wrigley Field during a 1945 World Series game. Located across the street, and practically beneath, the stately Tribune Tower on a gloomy stretch of Lower Michigan Avenue, the place is immensely popular with tourists. Even so, it's still a haunt for local reporters and advertising execs, and it still serves good, greasy cheeseburgers on fluffy buns. Take time to peruse the yellowed newspaper clippings and Hall of Fame photos that decorate the walls—they're a crash course in Chicago history.

Open Mondays through Fridays 6 am to 2 am, Saturdays 10 am to 3 am, Sundays 11 am to 2 am.

See + Do


Chicago offers some of the best live theater and concerts in the nation. Steppenwolf Theatre is the city's most famous performance venue, counting John Malkovich and Gary Sinise among its members. The Goodman Theatre consistently stages high-quality productions in both its 400-seat studio and its intimate 830-seat space. Chicago Shakespeare Theater stages first-rate productions at Navy Pier in a seven-story, glass-walled structure with panoramic views of the skyline. The Lyric Opera also aspires to a world-class standard, performing in the grand old Civic Opera House, and the Chicago Symphony is considered one of the three best in the world, next to Berlin and Vienna.

For comedy clubs and live music nightclubs, see our Nightlife section.

See + Do

Museum of Contemporary Art, Illinois

220 E. Chicago Avenue
Chicago, Illinois 60611
Tel: 312 280 2660

The MCA recently reasserted its position as one of the country's leading contemporary art museums with a highlights show that trotted out permanent-collection pieces by everyone from Francis Bacon to Andy Warhol. The museum, though, is more interested in keeping things cutting-edge and fun than in surveying even the recent past. More characteristic exhibits include Sympathy for the Devil: Art and Rock and Roll Since 1967, which used photos, paintings, film, sculpture, and music to explore the convergence of the two art forms. The museum's busy social calendar includes summer concerts on the lakeview terrace, First Friday events with DJs and drinks; and Sunday brunch at the ground-floor Puck's Café. Not enough fun? Try the MCA's double-decker gift shop, which stocks serious art books and artfully silly tchotchkes, including lots of Japanese action figures alarmingly armed with rocket launchers.

Open Tuesdays 10 am to 8 pm, Wednesdays through Sundays 10 am to 5 pm.

See + Do

Lincoln Park Zoo, Illinois

2200 N. Cannon Drive
Chicago, Illinois 60614
Tel: 312 742 2000

Occupying a beautifully landscaped strip of park in between the perfectly manicured streets of tony Lincoln Park and the shimmering waters of Lake Michigan, the Lincoln Park Zoo is the nation's oldest zoo (it was founded in 1868). It's also one of the last of its kind: A free—and incredibly well maintained—neighborhood zoo. Although it's charmingly small, you should still allow yourself two to three hours to wander the paths among landmark Georgian Revival brick buildings and colorful flower gardens. Main attractions include the Great Ape House (completely rebuilt in 2004) and the centrally located Sea Lion Pool.

Grounds open 9 am to 6 pm, buildings open 10 am to 5 pm. Call ahead for restricted hours in the winter and extended weekend hours in the summer.

See + Do


Chicago has 22 miles of lakefront bike paths. Rent a set of wheels (for about $10 per hour) at Bike Chicago (five locations including Navy Pier and North Avenue Beach). The company also conducts guided bike tours daily April through October. For a free bike map, safety tips, and rules of the road, contact the Department of Transportation's Chicago Bike Program.


See + Do

Art Institute of Chicago, Illinois

111 S. Michigan Avenue
Chicago, Illinois 60603
Tel: 312 443 3600

It takes several days to navigate this superb museum housing some 260,000 artworks—including some of the world's most famous masterpieces: Georges Seurat's A Sunday on La Grande Jatte, Edward Hopper's Nighthawks, and Grant Wood's American Gothic. There's an extensive Impressionist collection, and Asian holdings spanning five millennia that include one of the world's finest collections of Japanese woodblock prints. Don't miss the Chicago Stock Exchange Trading Room (a reconstruction of the Chicago Stock Exchange trading floor) or the Thorne Miniature Rooms, dollhouse-size re-creations of European and American interiors from the late 13th century to the 1930s.

The museum's steps are home to two photogenic lions (circa 1893) and provide a first-rate spot for people-watching. The even better spot, though, may be the Renzo Piano–designed Modern Wing of the Art Institute, which has helped draw a fresh crowd of art-lovers to the venerable museum since its 2009 inauguration. Like a big gulp of fresh air after the dark galleries of the original building, the wing is a homage to natural light. A flying carpet of aluminum blades mounted on the glass roof, a staircase suspended on slender rods, and high picture windows set a buoyant, clean tone for the collection of postwar and contemporary art, which includes all the approved masters, from Jasper Johns to Gerhard Richter and David Hockney. An additional big plus is Terzo Piano, a contemporary Italian-accented brasserie, headed by hometown former Top Chef contender Tony Matuano; the restaurant finally offers the hangout the Institute always needed.—Updated by Raphael Kadushin

Open Mondays through Wednesdays and Fridays 10:30 am to 5 pm, Thursdays 10:30 am to 8 pm, Saturdays and Sundays 10 am to 5 pm.

Information may have changed since the date of publication. Please confirm details with individual establishments before planning your trip.