CHICAGO is a city of storytellers. Lifers far outnumber transplants, and when roots run deep, mythos persists. So, drawing from the local knowledge passed down to me, I now present to you seven guiding Chicago principles.
Chicago rule number 1: never mention New York. Other than to say it’s OVERRATED, OVERCROWDED, and frankly, OVER THE HILL.
Chicago rule number 2: don’t read rule number 1 out loud – Chicagoans are proud folk with a low tolerance for BS.
A Chicago Whitesox game at Rate Field
Chicago rule number 3: no matter who you are, you are not too good or too fancy for the Guided Chicago River Tour. Forget open-top, big red buses. Forget Hollywood Hills stalking expeditions, because this guided tour is like no other. There are gold-crested relics of Art Deco’s Egyptomania period, alongside Brutalist megabuilds, and the modernist temple of American advertising that gave birth to the Marlboro Man and the Pillsbury Doughboy – “to this day cancer and obesity have never been so irresistible,” our guide concedes.
My personal highlight was the Marina City condominiums: twin, 600-foot concrete pinecones, the brainchild of curve-absolutist Bertrand Goldberg. Not a right angle in sight. Marina City is also a memorial to the king of cool, Steve McQueen, as the site of his final death-defying stunt. In The Hunter, McQueen launched a lime green ’79 Pontiac off the side of Marina City and into the Chicago River. The splash must have echoed right upstream; just a few months later, The Marlboro Man collected his wicked toll.
A guided river cruise with Chicago’s First Lady Cruises
For maximum effect, time your cruise for sunset before disembarking and stepping into the evening. Which brings us to rule number 4: bring cocktail attire.
Any Member’s Bar worth its salt has a healthy appreciation for mystery; an awareness that there’s a difference between exclusivity (shallow, unfulfilling) and secrecy. Nothing in the human condition is riper for titillation than the innate, childlike desire to be mystified; hence an almost standardised industry leaning into the aesthetics of mystery. However, 9 times out of 10, there’s no secret room behind that crushed velvet curtain, just a brick wall.
The Hand & The Eye Grand salon staircase
The people behind The Hand & The Eye, Chicago’s newest and most secretive members’ club, understand this better than most. Their solution to this mystery-drought? Magic, obviously. The Hand & The Eye occupies the entirety of a sprawling, beautifully maintained 18th-century mansion, but, in the spirit of secrecy, that’s all I’m obliged to share. Just rest assured that here, the velvet curtain is just the beginning.
Drag Brunch at The Kit Kat Club
Rule Number 5: when brunching, bring singles. Drag Brunch at the Kit Kat Club (in the LGBTQ+ hub, Lakeview) swings from funny to raunchy, to very raunchy, to oddly wholesome in the blink of an eye. The ABBA songbook via striptease on Mother’s Day morning felt like a perfect distillation of the art form. For a more sedate slice of Americana, catch a Sox game – as good a reason as any to visit Chicago’s oft-overlooked south-side heartlands. Whether it’s drag brunch or the foot-longs at Rate Field, save space for dinner, because Chicago is a proper food city.
Shanghai Terrace, at The Peninsula
The Bear stakes a claim to being both the de facto ‘Chicago Show’ and the de-facto ‘Food Show’ of the 21st century, so for the sandwich shop that inspired the pilot and appears as the backdrop, head to Mr Beef. Or (Rule 6), any one of Al’s, Portillo’s or Dijourno’s, because there’s amazing Chicago-style Italian beef sandwiches all over town. For something more refined (less napkins, more cutlery), the Shanghai Terrace at The Peninsula is a real showstopper. The best Dim Sum I’ve eaten outside of Asia, bar none.
The Peninsula Chicago Spa Relaxation Room
Finally, rule number 7: don’t sleep on Chicago’s art scene. Clear a whole day for the Chicago Art Institute and feast on a collection that, hand on heart, puts The Met to shame. For art you can touch, wear, pack and take home, squeeze in a visit to The Goody Vault, Chicago’s finest collection of rare vintage clothing, by appointment only – just ask for Manny.
by Charlie Navin-Holder
The Peninsula Chicago offers rooms priced from £350 per night
The Hand & The Eye offers the ‘Magic and Dining Experience’ priced from £176pp
The Chicago Architecture River Cruise offers tickets priced from £42pp
The Kit Kat Club offers tickets to the Drag Brunch priced from £54pp
Tickets to a White Sox game are priced from £8pp
For more information on Chicago, please visit www.choosechicago.com