Ah Chicago…. Chi-town, the second city and yes, windy, blowing right off lake Michigan. Where Route 66 begins and the twinkie was invented in 1930…though originally with a banana crème filling. It wasn’t until a banana shortage during WWII that it changed to vanilla. The Exposition of 1893 saw the first Ferris Wheel, the creation of the hot dog (a better way to sell sausages to a wandering crowd) and Pabst winning its famous blue ribbon. Where Natty Dresser Al Capone made $60 million selling illegal hooch, Ernest Hemingway got his start and Barak Obama launched his political career. And where the Cubs have played since 1871. Whether enjoying sports, dining on locally invented deep dish pizza or betting on the futures market, you will never be bored. A few things to amuse…
Chicago Architect Foundation River Cruises: Not the cheapest but definitely the best to discover more about the history of the buildings that make up the city where the skyscraper was invented and Frank Lloyd Wright left his mark.
Richard’s Fabulous Finds: The thrift store for your dreams… not your college toga party. Richard knows clothes. He spent years working for the likes of Ralph Lauren & Niemen Marcus and consulting on films and tv. He scours the world for unique and quality pieces. Most from the 30’s to 70’s… think rat pack chic.
Dusty Groove Vinyl: Two Uchic students started an online place to buy records in 1996, expanding to brick & mortar five years later before adding a record label to license rare tracks. They regularly acquire large collections including 40,000 titles from radio station WGN. Exploring in person is a must for anyone with a turntable!
Smyth Restaurant: Named after the small county in Virginia where chefs John and Karen Shields honed their skills, the tasting menus at Smyth are the stuff of dreams. Creative dishes, carefully sourced ingredients, knowledgeable servers… every bite perfection. And they play vinyl all night long! No wonder Michelin has awarded them two stars. I believe three will be coming soon.
Merz Apothecary: Only owned by two families since 1875, Merz is the place to go for great advice, neighborhood friendly service and an incredible selection homeopathic and natural self-care products. Their out post, Q Brothers focuses on men’s shaving products. The only downside, this landmark shop has become a stop on many tours. Visit in the off hours.
Bordel: Where Al Capone would hang out if he time-traveled to 2021, Bordel recreates the red velvet glamour of Prohibition. Low lighting, burlesque shows, live jazz and potent cocktails make this the perfect modern speakeasy. Located above Mama Delia restaurant you enter through an unmarked door at the top of a blood red staircase! Pay up for stage view.
The 606 aka The Bloomingdale Trail: Opened in 2015, this is Chicago’s answer to New York’s Highline, only wider. Built along a 2.7 mile stretch of defunct raised railroad line, you can walk, run or ride it’s length while admiring both permanent and temporary art installations along the way. The name comes from the 3 digits all zip codes in Chicago share. The city hopes to enlarge the trail and connect it to other parks over the coming years.