The Green Mill

Quite simply, the boss. Like a beautifully preserved Spitfire that not only still flies but offers skydiving tours, the Green Mill gives you all the thrills of going back in time. This joyous jazz joint has it all: authenticity without feeling like you shouldn’t touch anything; a crowd that likes to dress up but is not snooty; cocktails next to a bottle of Schlitz with a chaser Jeppson’sMalört, the city’s own super-hardcore liquor. “You can’t get more Chicago than that,” says owner Dave Jemilio of the killer combo.

This was an Al Capone favourite back in the 1920s, and you can sit in his booth (which has a line of vision to every entrance, naturally) and watch the show. Posters on the walls testify to the place’s past, with owners like “Machine Gun” Jack McGurn, part of Capone’s outfit, and acts like the comedian Joe E Lewis, who had his throat cut by McGurn over a contract dispute, yet lived to return to the spotlight. The Green Mill illustrates perfectly the difference between a theme bar and a real bar.
• Cocktails from $6, 4802 N Broadway Street, +1 773 878 5552, greenmilljazz.com

The Berghoff

When prohibition ended, The Berghoff was granted the first liquor licence in Chicago and the queues snaked round several blocks. That hallowed licence is still kept under glass for all to see, and the dining room is a fitting tribute to a family-run business that kept the city in “near beer” and good food through those ambivalent years. The restaurant section is a grand affair with murals depicting the World’s Fair of 1893 on its illustrious wooden walls, and serving German-American fare of wiener schnitzel, bratwurst and its signature creamed spinach.

As for cocktails in the bar, which is just as prestigious, anything goes. The head bartender, Sergio (who has sadly since moved on), took me on a mazy, hazy, trip through its history. Starting with the magnificent pre-prohibition Aviation – so called as the violet liqueur gives it a sky-blue colour, not as I assumed, as it makes you fly – then a Ward 8, a prohibition-era popinjay of a drink that was more prosaic than poetic in delivering alcohol, and a Vanilla Punch, which sent me into shivers of ecstasy. If you want proof of Sergio’s dedication to his craft, he makes his own tonic at home.
• Cocktails from $9, 17 W Adams Street, +1 312 427 3170, theberghoff.com

Coq D’or

The second place to get its liquor licence after the end of prohibition, the Coq D’or (pronounced Coke D’or) is a cosy, bijou bar in the basement of the Drake hotel. With the wooden panels and lanterns combining to cast long shadows across the elegant interior, it’s easy to feel like a private eye in a film noir. This is where men and women of status might come to discuss matters of great import, where Boss’s fictional Chicago mayor Tom Kane or the city’s real one, Rahm Emanuel, might discuss topics fiscal and foreboding.

And it does is cocktails of great standing, through the years, very well. It’s chronological drinks menu takes you from Bloody Marys in the 1920s and Margaritas in the 30s right up to Cosmopolitans in the noughties. And if you’re feeling opulent, try the “executive” size.
• Cocktails from $12, 140 E Walton Place, +1 312 932 4623, thedrakehotel.com

The Pump Room

This Chicago landmark fizzes with sophistication and the flamboyance of a bygone era. Situated inside the hotel Public and peppered with photos of celebrities from the 1920s to the present, it’s a place to throw back Moscow Mules and sample canapes. Try the Ginger Margarita or the North by Northwest, and if you manage to snag a table for dinner I would definitely start with the tuna tartare.

If you’re feeling regal, aim for the “phone table”; back in the day there was only one phone available for diners, and the most important person in the room was usually sat next to it. The phone is still there, on top of a table. Round the corner is the screening room – a furry chamber of deep sofas and secrets, shag-pile carpets and effortless pomp.
• Cocktails from $12, 1301 N State Parkway, +1 312-229-6740, pumproom.com

The Glunz Tavern

The Glunz family reopened the doors of this tavern recently after nearly 90 years of use as a storage room – and its proud history stares you down, from the perfectly preserved antique brass 10c beer signs to the dial on the vintage safe in the corner. Closed during prohibition, the tavern became a store for the wine and beer shop next door that made the family’s reputation, as connoisseurs of the grape, the hop, the juniper berry and pretty much everything else. It’s worth popping in for a look at this timeless emporium of fine tipples.

After that, pull up a stool or chair in the tavern and sample some of their superbly made 19th- and early 20th-century cocktails, like the Sidecar and the Sazerac. The food reflects the tavern’s German ancestry: coq au reisling, apfelstrudel and pretzel with beer mustard. The Glunz is the kind of place others spend millions trying to recreate, and fail – a genuine and habitable basilica to Chicago’s rich history, with the atmosphere to match.
• Cocktails from $10, 1206 N Wells Street, +1 312 642 3000, glunztavern.com

Mercadito/Double A

“It seemed I was just muddling my ass off,” says head bartender Paul Sauter, when thinking back to his days as a cocktail jockey in Miami, constantly making bog-standard mojitos. So when he came to this Mexican restaurant and bar in Chicago he came up with a drinks menu that turned tradition on its head. Enter the Whiskey Mojito and a host of concoctions that blended a knowledge of the best tequilas, mezcal, rums and gins with the freshest seasonal ingredients and a dash of improvisation: try the peachy Copper Canyon or the more zesty V-9. And the freshly made chips and tortillas are a perfect accompaniment to the onslaught of flavours, and the mango guacamole seals the occasion.

Downstairs, Double A offers a speakeasy experience. Peer through a wooden slat to be admitted into this drinking foxhole. An open mixing area means you can get involved or simply watch close up as you sample an Old Smashion – like an Old Fashioned with mezcal instead of whiskey, invented by Paul – a white rum-based Wise Old Sage, or take inspiration from Mercadito’s name and try the Little Market, infused with sunshine (not literally).
• Cocktails from $11, 108 W Kinzie Street, +1 312 329 9555, mercaditorestaurants.com, doubleachicago.com

Trenchermen

A converted Turkish bathhouse in the Wicker Park district, Trenchermen splashes you with chic and fans you with panache, as you settle in among its white bricks and hardwood finery. It seems part cocktail bar, part gastropub and part opium den; a louche woosh of tantalising odours and animated conversations, lubricated and maintained by a pulsating bar area and a roaring kitchen. Try the salmon tartar with brioche and the crudites with your drinks, and if you leave without sampling the pickle tots – potato and gherkin in divine union – you are a fool and should be banished from the city limits. Drink a Pioneer, which has whiskey and Campari in it and yet is somehow nice, absorb the warmth of a Rumpelstiltskin, with orange peel rum and apricot, and give yourself an Ultimatum, with tequila and green chartreuse.

Naturally, as this is Chicago and I seemingly can’t escape it, the Malört comes out. But this time, instead of the more common Jeppson’s variety, master bartender Tona Palomino sidles over like an urbane tumbler-toting assassin and invites us to sample his own barrel-aged Malört, which is smoother and tastes a bit stronger. If you stay for dinner have the hake. Or the skate. Or the duck. In fact, have them all, along with the gnocchi and a cider doughnut for dessert. When you’re at Trenchermen, it’s easy to act like one.
• Cocktails from $10, 2039 W North Avenue, +1 773 6611540, trenchermen.com

Scofflaw

The name comes from a term first minted during prohibition, and applied to someone who regularly flouted the booze ban. Not necessarily because they were criminally minded, but because they saw the law itself as an abomination. This newish gin joint – even the mussels are served with a gin sauce – is similarly pugnacious in its outlook. It takes some of the more hackneyed notions of the bar industry, pops them into a mixer with some garnish and ice, and gives them a good shaking.

It charges $8 for practically everything on both the drinks and snacks menu, and as my buddy Lou, a son of Chicago, pointed out, for a high-end bar in the city, “It actually treats you like you belong there, not like you’re lucky to be there”. It makes its own Old Tom gin, and with drinks like the Pellet Gun, burnished with what my friend Livya described as “some delicious pink stuff”, and the Lonesome Hero, with tequila, Aperol and “banana ice”, you’ll be baffled and happy and itching to come back.
• Cocktails from $8, 3201 W Armitage Avenue, +1 773 252 9700, scofflawchicago.com

The Gage

While this list can be accused of criminally neglecting the South Side’s best spots and focusing too much on central Chicago, that is most likely where as a visitor you’ll spend most of your time, on your first visit anyway. And at some point you’ll end up in The Loop – the central business district that borders Lake Michigan and contains Millenium Park, home of Anish Kapoor’s sculpture the Cloud Gate (known locally as the Bean), the Frank Gehry-designed concert hall and the Art Institute, plus the Magnificent Mile of shops and arcades along Michigan Avenue.

And after a hard day of culture and consumerism, the Gage is a perfect place to refuel and rejuvenate yourself. A signature Gage cocktail with pear vodka and clove-infused apple juice, and a freshly made scotch egg appetiser should relight your fires, while a Sonic Boom, with tequila and “pineapple foam” may set your ambitions ablaze. This place is cosy in winter and breezy in summer, a great spot from which to watch the city walk by.
• Cocktails from $12, 24 S Michigan Avenue, +1 312-372-4243, thegagechicago.com

Phil Stefani’s 437 Rush

There’s now a steakhouse and Italian restaurant out the back, while the front bar revels in the venue’s marvellously sketchy history. A giant mural pays tribute to its makeover from speakeasy to the infamous Riccardo’s back in the 30s – the city’s fulcrum for musicians, poets, political types, gangsters and journalists at one stage or another, with a bar shaped like a treble clef paying dues to it reputedly being the birthplace of live jazz. Cocktails range from the rugged taste of the Chancellor – all port, orange peel and determination – to the more epicurean delights of a Fudgesicle – with chocolate and Bailey’s and insouciance. On the food front, the fresh pastas and sliced meats will blow your sax off, and the sea bass is acknowledged to be among the best in the state.
• Cocktails from $11, 437 N Rush Street, +1 312 222 0101, philstefanis437rush.com

The trip was organised by Choose Chicago, with accommodation at the Drake Hotel (doubles from $139) and Public (doubles from $175). United flies from Heathrow to Chicago from £557 return, including taxes