By Amy Bizzarri
Optimo Hats and Chicago theatre images – credited to Paul Beaty
Writer Nelson Algren summed it up best when he said, “Loving Chicago is like loving a woman with a broken nose.” She might have some glaring flaws, but she’s so beautiful, with such a heart of gold and such an indomitable spirit, you can’t ever seem to let her go. She is a city “singing so proud to be alive and coarse and strong and cunning,” as described by poet Carl Sandburg. Chicago started off as a small fur trading settlement and rose into a metropolis in a span of less than 250 years, refusing to let even a massive fire get in her way. She’s one tough lady. Today’s Chicago offers a hip, urban vibe amidst the stately skyscrapers, but you’ll still find plenty of retro flair. Here is your guide to Chicago’s vintage gems.
With its six-story high “C-H-I-C-A-G-O” sign and iconic marquee shining brightly on State Street, the landmark Chicago Theatre still stands as one of Chicago’s best – and certainly most beautiful – entertainment venues. Dubbed “the Wonder Theatre of the World” when it opened on October 26, 1921, it was the first large, lavish movie palace in the U.S. To this day, the Chicago Theater still draws in the best and brightest players in show business, from Dolly Parton to Diana Ross, from Frank Sinatra to Arethra Franklin. 175 N. State St.; (312) 462-6300; thechicagotheatre.com
GREEN MILL COCKTAIL LOUNGE
If the walls of the Green Mill could talk, they’d have so many soulful and passionate stories to tell. From the jazz greats – Billie Holiday, Von Freeman, Wilbur Campbell, Kurt Elling, Orbert Davis – who once mesmerized audiences in the once smoke-filled lounge – to the mobsters and movie stars that once mixed and mingled over martinis in this timeless jazz bar, the Green Mill is haunted with legends of long ago. For over 100 years, Ceres, the Goddess of Harvest has watched over the crowds in this Art Deco gem, the best jazz club in Chicago, and likely the world. 4802 N. Broadway St.; (773) 878-5552; greenmilljazz.com
CAPE COD ROOM
The legendary Cape Cod Room opened on December 6, 1933, just in time for Chicago’s Century of Progress World’s Fair in 1933, and, perhaps more importantly for the success of the restaurant’s bar, the day after the 21st Amendment was ratified, bringing an end to Prohibition. The dining room decor hasn’t changed much since opening day: the walls are still covered in wooden oars, nautical memorabilia, and taxidermied fish, crabs and lobsters and the Dover sole meuniere is still prepared tableside. Sit at the wooden bar and order some freshly shucked oysters and a glass of straight gin: See if you can spot the initials of Joe DiMaggio and Marilyn Monroe, carved into the northern end of the wooden bar while they were on a whirlwind date at the Cape Cod Room in 1954, the same year they married and divorced. 140 E. Walton Pl.; (312) 787-2200; thedrakehotel.com/dining/cape-cod
THE CHICAGO ‘L’: EST. 1892
Short for “Elevated”, the Chicago ‘L’ has been serving Chicago since 1892, making it the second-oldest rapid transit system in the Americas after Boston’s. Step up and onto the Brown Line, stop at the corner of Madison and Wabash streets and enjoy the view from the elevated tracks as you circle the Loop, Chicago’s business center.
LEE’S UNLEADED BLUES CLUB: EST. 1983
Don’t let the plain brick exterior fool you: this lounge has been a South Side blues hotspot since the 1970s, when it was the infamous Queen Bee’s Lounge, host to such blues legends as Junior Wells and Lefty Dizz. Infectious melodies still ooze out of the club as soon as the door is opened. 7401 S. Chicago Ave; (773) 669-5053; leesunleadedblues.com.
ART INSTITUTE OF CHICAGO: EST. 1882
The world class Art Institute of Chicago boasts over 260,000 masterpieces, from the mummy case of Paankhenamun to Grant Wood’s American Gothic. Be sure to visit the Impressionist collection: many of the paintings were acquired by Chicago socialite Bertha Palmer in the years leading up to the 1893 Columbian Exposition, when she was a client of the Parisian art dealer Paul Durand-Ruel. 111 S. Michigan Ave.; (312) 443-3600; artic.edu
Chicago has always been a hat-wearing town, with new styles of classic men’s hats hitting the streets every decade. Take a look at any street scene photo of Chicago pre-1960s, and you’ll be hard pressed to find a man not wearing a hat. Handcrafted in Chicago, Optimo hats are collectors’ items; take good care and they’ll last for generations. The small shop in the Monadnock Building is small yet stately, the walls and display windows lined with perhaps the most beautiful men’s hats you’ll ever encounter. 320 S. Dearborn St.; (312) 922-2999; optimo.com
Amy Bizzarri is a Chicago-based writer who loves exploring her city by bicycle. Her most recent book, Discovering Vintage Chicago, was published this year by Rowman Publishing.