Easing into a night at the theater with a pre-show dinner or capping it off with a cocktail can transform a two-hour show into a true night on the town. Chicago's theaters feature spectacles of all stripes, so finding a restaurant or bar to complement the experience (and your potentially posh dress) involves a bit of a search. These pairings aspire to behave like a good wine, enhancing the flavor and mood of your night as an audience member.
Taking in Broadway
Start with appetizers and a candy-colored cocktail at Atwood Cafe
Then a musical at Ford Center for the Performing Arts, Oriental Theatre
If you're lucky enough to score tickets for the bewitching Broadway hit, a "Wicked" pre-show meal is in order. Kick start an evening of color and whimsy at the Atwood Cafe, located about a block south of the theater in the Hotel Burnham. The first thing you'll notice at Atwood is the unusual decor: chandeliers dripping in ruby-colored stones wear multiple strands of pearls, a high, tilted mirror skews perspective behind the bar and shades of gold, blue, black and red create a dramatic visual symphony throughout the space. It's like taking tea at the Mad Hatter's table, though in this case, you can swap tea for contemporary American fare like rosemary-crusted pork tenderloin ($17-$29). This wonderland can get pretty crowded around show time, so try to make a reservation. As for attire, if you've forgotten your ruby slippers just take your casual gear up a notch.
A downtown tradition
Start with a seasonal cocktail and home-style cookin' at the South Water Kitchen
Then a drama at the Goodman Theatre
The Goodman Theatre has graced Chicago with dramatic productions since the 1920s. An evening at this theater is a few hours spent in a Windy City institution, so grab some pre-show grub that melds with the Americana mood. Located just a few blocks from the Goodman but far away enough for comfort (meaning no herds of hungry audience members), the South Water Kitchen provides the perfect locale for some home-style fare. The dining room's Tuscan yellow walls showcase photos of old-time movie stars, and cozy banquettes glow in the intimate light of the beaded lamps that decorate each table. The exhibition kitchen may as well be Mom's: full of hanging copper pots and quaint bread baskets. It's best to make a reservation if you plan on conquering the Kitchen before show time. Whatever you're wearing to the Goodman will work out at this restaurant; nobody's going to look at you funny for downing chicken and dumplings in your Sunday best.
Imported elegance in the Loop
Start with Old World fare at Russian Tea Time
Then a classical concert at Chicago Symphony Orchestra
When dedicating an evening to lyric ballads of Old World Europe, start the glamour off right at Russian Tea Time. Located just around the corner from the CSO, the restaurant was founded by a straight-from-the-USSR mother and son duo in 1993. Familial warmth is the order of the day in this jovial place for latkes and vodka flights. The staff earns accolades for hospitality, and if you want to learn some tips for tipping back shots, they're happy to offer guidance. The restaurant's decor channels imperial Russian style: convivial shades of red highlight the room and light twinkles softly from chandeliers. Get a little gussied up for the occasion and have your Cher (or Nick Cage) in "Moonstruck" moment; it's not every day you get to go the symphony. Tip: On Friday and Saturday nights, the restaurant stays open till midnight to accommodate post-concert strudel cravings.
Joking around Old Town
Start with a belly-laugh at Second City
Continue the fun at Wells on Wells
In the olden days, waiting by the stage door was the only way to meet the cast. But if you've just caught a side-splitting parade of shenanigans at Second City, head across the street to Wells on Wells and wait for the cast to trickle in for a post-show libation. The neighborhood bar features the full roster of drinks, so if you're feeling fancy you can eschew Miller Lite in favor of some Grey Goose. Just don't order a mojito, please; Wells is bigger on good vibes than on fancy garnishes and $12 drinks. A menu of typical bar fare will quench any cravings you've worked up over jokes. Located directly across the street from Second City, this place is a convenient and friendly a place to keep up the wisecracking.
Hollywood chutzpa on Halsted
Start with a movie star sighting at Steppenwolf Theatre
Finish in 1940s-Hollywood style at Landmark
With such megawatt stars as Gary Sinise and John Malkovich treading its boards, the Steppenwolf Theater brings a bit of Paramount to Chicago. After hanging out with the boys of the big screen, head across the street to Landmark. The restaurant/bar/latest hotspot from the Boka crew sports a 1940s-Hollywood theme that immerses martini-sippers in a "Sunset Boulevard" ambiance. Grab a specialty martini at the burgundy leather bar (the Chai flavor's a sweet bet) or settle into a curved banquette to sample some pizzas from the wood-burning oven. Upstairs, the Blue Dining Room provides a glamorous and moody-hued spot for post-show discussions. In keeping with the silver screen theme, don your A-list attire.