Sweet Home Chicago: 9 Ways to Explore the City

Make your trip line up with your style. From foodies to music mavens, here's how to find the perfect Chicago adventure for you.

Ole’ Blue Eyes sang her praises: “Chicago is my kind of town.” The locals speak just as plainly, and without pretense. It’s not like a Midwestern to brag—with words, anyway. We use our skyscrapers to speak our power. We embrace our teams in the good times and bad times, and boy, there have been bad times. We eat without regard to how others will judge us: from deep-dish pans, gut-busting tasting menus, even from test tubes. Whatever your travel style, Chicago can be yours—however you like it.


The Foodie

With so many great restaurants in this city, we begrudgingly choose one: Brindille, a James Beard nominee for Best New Restaurant. Siblings Carrie and Michael Nahabedian tempt our tastebuds with veal sweetbreads, a lobster brindille and a noisette of lamb saddle. Naha, also a Nahabedian production, is the Michelin-starred sibling next door. 534 N. Clark St., 773.595.1616, www.brindille-chicago.com

The Family

For what could be a big, scary terrain, Chicago is easy to navigate with kids. By train: Loop the Loop on the Brown Line (a mini architecture tour in itself) or take the bus to Navy Pier (600 E. Grand Ave., www.navypier.com), home to a 15-foot Ferris Wheel and three-story Chicago Children’s Museum. Traveling by car? Head to the Museum Science and Industry for the final weeks of the "Treasures of the Walt Disney Archives," a tribute to the Chicago-bred magic maker. (5700 S. Lake Shore Dr., www.msichicago.org)

Chicago's Navy Pier
Navy Pier in full swing (Courtesy Navy Pier)

The Architecture Buff

Learn how the land of the "wild onion," became, building by building, the metropolis it is today via the chatty and knowledgeable volunteer docents aboard Chicago's First Lady, whose cruises start April 5. Find the dock at the southeast corner of the Michigan Avenue bridge. Ticket prices and times vary.

Chicago's First Lady tour boat
Touring Chicago by water (Courtesy Chicago's First Lady)

The Soloist

A comfy seat awaits at I|O Urban Roofscape, the sultry lounge with a retractable roof at The Godfrey. With glorious, Southern-facing views of River North, you'll enjoy small bites and chef-driven mojitos. Toast to not being here during thundersnow season. 127 W. Huron St., 312.649.2000

I|O Urban Roofscape's hip lounge atop The Godfrey Hotel Chicago
I|O Urban Roofscape's hip lounge atop The Godfrey Hotel Chicago (Courtesy the Godfrey, Chicago)

The Drama Queen

You firmly believe the world is a better place because of Kristin Chenoweth, Nathan Lane and the “Phantom.” Embrace the glitz of Broadway in Chicago productions (www.broadwayinchicago.com), savor the grit of Steppenwolf (www.steppenwolf.org) or the imagination of Lookingglass (www.lookingglasstheatre.org). No melodrama if a show’s sold out, honey: HotTix sells discounted day-of seats (three downtown locations and online at www.hottix.org). 

Chicago's Steppenwolf Theatre
Chicago's Steppenwolf Theatre (Courtesy Steppenwolf Theatre)

The Shopper

Easy-off shoes. Yoga pants. Freshly paid-off credit card. You're ready to shop. The Mag Mile can take a day alone, what with three malls and about 500 other stores. Tip: Grab coupon books at the mall info desks. State Street beckons with a flurry of low-price retailers and indoor shopping at Block 37 (www.block37.com). Or hop the Blue Line El to Damen and get off in Bucktown/Wicker Park’s indie boutique central.

The LGBT Traveler

Set up home base at Halsted and Roscoe streets in Boystown. From here, stock up on glitz costume wear (Heels for a size 12? No problem.) at Beatnix (3400 N. Halsted St., 773.281.6933, www.beatnixclothing.com) and grab a bite at skewer sweet spot mEAT (3339 N. Halsted St., 773.871.2662, www.eatatmeat.com) before the DJ drops that first beat at the stylishly luminescent nightclub Progress (3359 N. Halsted St., 773.697.9268, www.progressbarchicago.com).

Skewers at mEAT (Courtesy mEAT)
Skewers at mEAT (Courtesy mEAT)

The Museum Hopper

With admission to five top destinations built into the $89 price, CityPass is the best way to see the Seurat at the Art Institute of Chicago (111 S. Michigan Ave., 312.443.3600, www.artic.edu), belugas at Shedd Aquarium (1200 S. Lake Shore Dr., 312.939.2438, www.sheddaquarium.org), and Sue the T.Rex at the Field Museum (1400 S. Lake Shore Dr., 312.922.9410, www.fieldmuseum.org) for less than a Benjamin.

(Courtesy Art Institute Chicago)
(Courtesy Art Institute Chicago)

The Music Maven

Not your style to catch a show from the 388th row? Leave it to Schuba’s (3159 N. Southport Ave., 773.525.2508, www.schubas.com) to bring big names into a venue where you can get close enough to smell their sweat. Past performers include The National, Norah Jones and Bon Iver—and the lineup is always good.