Discover Chicago’s Vintage Charms

Poet Carl Sandburg once described his hometown of Chicago as “singing so proud to be alive and coarse and strong and cunning”, a statement that honors the indomitable spirit of a city that started off as a small fur trading settlement and rose into a metropolis in a span of fewer than 250 years. Today’s Chicago still sings, while also offerings a hip, urban vibe amidst the stately skyscrapers. Best of all, you’ll still find plenty of vintage flair. Here is your guide to five Chicago vintage gems that promise to transport you to another era altogether.

Green Mill Cocktail Lounge

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. Don your best vintage dress and plan on dancing the night away in this iconic, picture-perfect cocktail lounge.
Even though he owned a speakeasy in the basement across the street, gangster extraordinaire Al Capone loved the Green Mill Cocktail Lounge. When Scarface entered, the bandleader knew best to pause everything and play Rhapsody in Blue, STAT. From his favorite moss green velvet-lined booth, the one directly across from the side door entrance on Lawrence, near the end of the bar, Chicago’s Big Fellow, as his criminal associates called him, could assess whoever entered the bar while also simultaneously soaking in whatever act was onstage.

If the walls of the Green Mill could talk, they’d have so many soulful 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.

4802 N. Broadway St.
(773) 878-5552

Aragon Ballroom

Soon after it opened in 1926, the Aragon was flooded with music-loving Chicagoans. They came by L, thanks to the nearby station and packed the station to capacity on each and every night of the six-day business week. Hit station WGN broadcast live from the Aragon, furthering its appeal among the young and musically inclined. Newspaper advertisements for the ballroom vaunted “visions of languorous senoritas and dashing caballeros” and “moondrenched patios and stately turrets gently brushing Mediterranean skies”; a postcard boasted “He Who Has Not Been At Aragon Knows Not What A Paradise It Is!”

Supernatural, musically enveloping experiences have become almost common place under the twinkling stars of the Aragon Ballroom. Grunge band Nirvana played their final show here, performing the long-bootlegged, beloved song You Know You’re Right. Green Day filmed their “MTV Jaded in Chicago” concert to a sold-out crowd here; funk metal band Primus filmed their first concert DVD, Hallucino-Genetics from the Aragon’s stage; sludge metal band Masto don recorded a live album and concert DVD, proving that every genre can find their magic in the enchanting Spanish village within a ballroom that is the Aragon.
According to legend, secret tunnels leading from the Aragon’s basement to the nearby Green Mill bar provided an easy escape for music-loving mobsters. Al Capone sat in his private, southwest balcony booth where a fire escape guaranteed an easy exit. The ballroom’s basement doubled as a speakeasy run by bootlegging king Hymie Weiss and the gang of Charles “Deanie” O’ Banion, a Capone rival who was later gunned down while clipping chrysanthemums in his family-run floral shop.
In the ’60’s the Aragon morphed into a mod discotheque; in the ’70’s it became the home of Monster Rock marathons and earned the badge of a nickname “the Aragon Brawlroom.” Today, you’ll find an eclectic calendar of concerts featuring just about every genre of music you can imagine, from rap to reggaton.

1106 W. Lawrence Ave.
(773) 561-9500


Chicago has always been raucous, wild and dirty in more ways than one. From the early 1880’s until the early 1930’s, the city played host to a hot vaudeville theater scene, where burlesque dancers performed scintillating, and sensational shows. Arrests for indecent exposure commonplace. Star strippers made their names on the Chicago vaudeville scene, especially Sally Rand, who performed her sensational ostrich feather and fan dance at the 1933 Century of Progress (and was subsequently arrested four times in a single day). Then came Prohibition, and the first nudie films of the 1970’s, and the sun seemed to have set forever on the playful, powerful art of burlesque.
Enter Vaudezilla, where a new generation of sassy and sexy performers are finding their footing and bringing burlesque back to the Chicago theater scene.

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Vaudezilla is an academy of all things burlesque, a place where even the most bashful babe can conquer her fears and hit the stage with a sexy act of her own. Born in 2008 when solo Chicago burlesque performer Red Hot Annie teamed up with Keith Emroll (aka Dick Dijon) the school offers classes in everything from slapstick tease to boa dancing to fan veil mastery. The small studio space is intimate; the instructors embracing.
For those jonesing to give burlesque a go, Vaudezilla’s Cabaret Showgirl intensive, a series of intensive workshops that include both one-on-one coaching and group exercises, completely immerses attendees in the day-to-day creative process of a modern burlesque performer. On the last Friday of the camp, attendees will be all set as they perform onstage for the very first time, in their new, burlesque persona.
“Students come to Vaudezilla expecting to learn how to dance and to feel sexy in their own skin while they do it, and our burlesque classes accomplish that,” explains owner Red Hot Annie. “But the thing I hear over and over again is how empowering it is to embrace yourself in class and onstage. Confidence, taking up space, and the ability to hold the attention of a room are skills that apply to everything from personal relationships to public speaking, and they are skills you can learn through burlesque.”
Vaudezilla also hosts a number of free, community events each month, including the popular Craft and Crab sessions, the burlesque version of a “Stitch and Bitch,” where you can drop by with your latest work in progress, chat, vent, and make new friends while working on your costume.

3614 W. Belmont Ave.
(773) 558-0081

Garfield Park Conservatory

Garfield Park Conservatory is the perfect tropical vacation spot within the city. At 4.5 acres, this botanical treasure is one of the largest greenhouse conservatories in the United States. Located in the midst of historic Garfield Park on Chicago’s West Side, the conservatory was designed by renowned Prairie Style landscape architect Jens Jensen and opened to the public in 1907.

Jensen’s goal of recreating naturalistic landscapes under the glass top, a revolutionary idea at the time, is no more evident than in the Fern House, where so-called primitive plants – plants that grew during the age of the dinosaurs, about 300 million years ago – rest on rocky outcroppings and surround a koi-filled lagoon. The waterfall at the back of this room is a reminder of Jens Jensen’s unique, perfectionist vision for this particular house of the conservatory: He forced his mason build and rebuild the bubbling waterfall several times until the falling water trickled to the beat of Mendelssohn’s ‘Spring Song’.
Plan on spending a couple of hours strolling among the conservatory’s beautiful flowers. The Garfield Park Conservatory is incredibly picture-perfect, so plan on snapping several Instagram-worthy images with flowers and plans from around the world as your one-of-a-kind backdrop.

300 N. Central Park Ave.
(312) 746-5100

Optimo Hats

There was a time when a man would have felt naked strolling the streets of downtown Chicago without a dapper hat on his head. The city had always been a hat-wearing town, with new styles of classic men’s hats hitting the streets every decade. Smart hats were de rigueur for the modern man, no matter his profession, social status, or stature. Take a look at any street scene photo of Chicago pre-1960, and you’ll be hard pressed to find a man not wearing a hat.

Optimo Hats
Then came John F. Kennedy. He wore a top hat on their first day on the job, a presidential tradition, but was rarely seen with a hat of any kind on during the course of his presidency. His fellow American men followed suit, and here we are today. Though it’s now uncommon to spot a man wearing a stylish hat, Chicago custom hattery Optimo Hats is on a mission to bring back the bold, elegant statement hats to bare-headed men everywhere.

The small shop in the 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. You can get fitted here for a custom hat with the help of the retro circumference measuring tool, and a flange stand, used flatten and shape the brim to your tastes. For inspiration, old advertisements for the latest hat styles are posted along the wall at the main entrance. The professional sales staff at both locations help customers find that perfect fit, which should gently grip your head and be able to be pulled down a bit when the windy city lives up to its reputation.

Optimo hats are collector’s items – take good care and they’ll last for generations. The fact that they are completely handcrafted from the finest materials sets them apart from the rest. Straw hats are made from the highest quality woven straw imported from Ecuador while the felt of their fedoras is crafted from wild animal furs, as opposed to the cheaper wool alternative. Prices match the time-consuming process, with the most expensive hats running in the thousands.

320 S. Dearborn St.
Chicago, IL 60604
(312) 922-2999


Amy Bizzarri is a Chicago-based writer who loves exploring her city by bicycle. Her most recent book, 111 Places in Chicago That You Must Not Miss, explores Chicago’s hidden corners and secret history.

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