The Ultimate Guide to Chicago For The Man Of Style

C

Chicago, Chicago I Will Show You Around…

As Frank Sinatra crooned, “Chicago is my kind of town,” and I couldn’t agree more. I was born and raised here. I’ve traveled the world, studied abroad, worked and lived in difference cities, but I’ve spent 31 of my 38 years in Chicago. And I believe Chicago is the “goldilocks” of American cities: not too big (see: New York City) nor too small (see: Boston); not spread apart (see: LA or Dallas) nor crowded (see: New York City, again).

The “city of big shoulders” has more culture than you could fit into multiple lifetimes, a vibrant fabric of neighborhoods filled with even more vibrant people, a world-renowned skyline, a lake that’s as good as either coast, and a cost-of-living that that’s better than both.

Like all world-class cities, Chicago is a playground for a man of gentlemanly pursuits—from food and drink to shopping and experiences, the city has it all. And whether you have yet to experience the magic of Chicago yourself, are already a frequent visitor, or are a lifetime resident like me, I hope this guide makes you anxious to plan your next night out in the Windy City.

Where to Shop

Ralph Lauren Flagship on Michigan Ave. (River North)

Stepping from Michigan Avenue into the mansion that is Ralph Lauren’s four-story flagship in Chicago is like transitioning into another world. Your experience begins in the stunning, wood-paneled main floor featuring an elegant grand staircase flanked by immaculately framed art, making you feel more like a welcomed guest at some high-society dinner party instead of a wide-eyed tourist.

The second level is home to my favorite room – the suiting room – that without fail features expertly dressed mannequins, in Ralph’s best (usually Purple Label). They are always perfectly coordinated with the season (tweed in the fall, velvet and black tie in the winter, creams and beige in the spring).

A gorgeous level for women on the third floor leads the way to the fourth floor dedicated to Ralph’s interior design. Every nook and cranny is decked out with contemporary plaid, silver-plated frames, beautiful cocktail glasses and barware.

And, lest I forget a very important detail, this flagship is connected to the RL Restaurant (literally, there’s a glass paneled door on the main level of the flagship that opens into RL’s handsome bar) where you can refresh yourself after some retail therapy with a martini without ever stepping back on Michigan Avenue.

BLVDier (West Loop)

Full disclosure: I’ve not yet been a customer here myself (operative word being “yet”). But, what I believe is a bigger validation, the most stylish guys I know in Chicago – the ones who care about the drape of their jacket and the size of their lapels; the ones who know how to pair a dark blazer with light trousers; the guys who make an effort to look their best when they’re out on the town – all swear by BLVDier. Which, by extension, means Zach, the shop’s elegant Founder / Owner) for their made-to-measure menswear needs.

Many of these friends have trusted Zach with the most important day of their lives and their wedding tuxedos have been the work of art, creating wedding photos that truly belong in a fashion magazine. Recently I reached out to friends who had used Zach in the past, one said he’s “[planning] to get in touch with him for a tweed this winter” while another said, “I think their price to quality ratio is the best in the city”.  For me, that’s all I needed to hear to know where I’ll be going for my next MTM piece.

Mildblend Supply Co. (Wicker Park)

Any hardworking city that isn’t afraid to get its hands dirty needs a top-notch denim shop and, for Chicago, that’s Mildblend. As a recent novice to selvedge denim, I can attest that the staff here are incredibly friendly and helpful for anyone looking to start on the addicting, yet fulfilling, selvedge journey. And I also wager – given the shop’s extensive supply of denim from all over the world – that selvedge veterans will have a field day here as well.

Not only do they sell the goods, but when your put-to-work denim no doubt requires some gentle TLC (in my case, some unfortunate tears in the posterior region), Mildblend’s repair service is impeccable, applying a dizzying array of literally thousands of minute sews that return the jeans to nearly new condition.

Merz Apothecary (Lincoln Square)

What began as a pharmacy in 1875 (!) is now, arguably, home to the best selection of men’s grooming products and – my personal favorite – luxury scented candles in Chicago. A trip to Merz will undoubtedly make you question the difference between life’s necessities and life’s luxuries.

For example, Lafco’s incredible range of candles (“Ski House” is my all-time favorite) or Penhaligon’s elegant and sophisticated fragrances from England (“Juniper Sling” is essentially the bottled version of a freshly made gin tonic) – and will absolutely help fill out your birthday or holiday wish list.

Richard’s Fabulous Finds (Humboldt Park)

Sometimes, shopping can transcend a simple financial transaction, and instead becomes an experience, a memory and a story all its own. Visiting this expertly curated little hamlet of a men’s vintage store offers just that.

For nearly a decade, Richard’s Fabulous Finds has provided Chicagoans an unrivaled selection of vintage menswear – from sweaters to blazers, cufflinks to bowties, and everything in between – most with some fascinating story of origin and all hand-selected by the delightfully dandy eponymous owner himself, Richard. It’s a wonder how he fits it all in a storefront that doesn’t feel much larger than a living room, but that “bursting at the seams” energy gives Richard’s a welcoming coziness that encourages you to linger and browse.

Whether you’re coming in with a very specific plan (say, a roaring 20’s office holiday party) or are looking for some guidance (August wedding in the South, “help!”), you couldn’t be in better hands than Richard’s, where his keen and timeless style eye mixed with his charismatic flair will have you looking – and feeling – your best.

Where to Eat

Bavette’s Bar & Boeuf (River North)

No list of where to eat in Chicago would be complete without a steakhouse included. And of the many great options at the fingertips of Chicagoans – Gibsons (original and Italia), Swift & Sons, and the old school Gene & Georgetti’s – Bavette’s rises above them all. It’s got a menu studded with more stars than Hollywood Boulevard all served in one of the toniest restaurant ambiences I’ve ever experienced.

Bavette’s menu doesn’t change that often and when you get as much right as they do, that’s a good thing. I always start with the egg-yolk topped silky beef tartare accompanied by huge slices of freshly baked sourdough and follow that up with the sensory delight that is their smoked trout Caesar (a signature dish that can sometimes be found in other Hogsalt establishments).

For the main event, you have all the selection you would want from a top-tier steakhouse – wet- or dry-aged, boneless or bone-in – each paired with Bavette’s homemade bearnaise sauce and steak salt. This seemingly pedestrian combination of three basic things – beef, a French sauce, and a small dish of simple seasoning – work in such orchestrated harmony together. They deliver bites bursting with such flavor and decadence that you can’t help but smile.

As you enjoy this meal within Bavette’s swanky dining room where 1920s jazz provides the soundtrack to dancing candlelight and dim-lighting, you’ll find yourself wishing your espresso (and your evening) was bottomless.

Monteverde (West Loop)

Monteverde is everything a contemporary Italian restaurant should be in every way. Welcoming and relaxing. Bright and airy. Elevated and yet without any pretention. Award-winning Chef Sarah Grueneberg’s cuisine follows suit, with dishes like the “burrata e ham” with a rosemary tigelle (essentially a little bread pillow kissed by a sprig of rosemary) and “cacio whey pepe” that uses ricotta whey to elevate a classic. These are dishes that use simple ingredients to create a work of art that tastes even better than it looks.

The restaurant’s angled mirror high above the open kitchen gives diners the captivating view of pasta chefs handmaking the noodles from scratch. It provides in-meal entertainment while also promoting the sense that you’re at a casual dinner party, chatting with the host as dinner is prepared.

Mama Delia (Wicker Park)

While flying to Spain on a whim is a great flex, that’s not something we can all fit into our lives (or our bank accounts). Instead, Mama Delia offers Chicagoans an intoxicating and delicious evening escape to Spain (namely, Valencia, where Chef Marcos Campos is from), with a menu bursting with flavor and a vibrantly decorated space to match.

From massive scallops served on a beautiful seashell and drizzled with basil oil to mushroom croquetas dolloped with a sherry-infused foie mousse, your tastebuds will be in Spain even if you physically aren’t. Salty boquerones and pan con tomate are always good additions to the table. Plus, a trip to Mama Delia’s isn’t complete without one of their family-style paellas (my favorite being the arroz negro, made with squid ink and served with head on prawns).

And since no one wants a trip to Spain to end early, you can clean your palate at Bordel (Mama’s Delia’s sister bar right above it), where you can order a nightcap of traditional Spanish porron or something off the bar’s impressive sherry menu.

Bistro Campagne (Lincoln Square)

Not to be confused with champagne (although there certainly is plenty of that here), “campagne” in French is colloquial for “country,” and this little hamlet in Chicago’s Lincoln Square neighborhood is exactly that: an adorable French country bistro that just so happens to be on one of the busier streets in the neighborhood.

Bistro Campagne’s menu stands up to any traditional and unpretentious French restaurant. Its delicious mainstays like escargot, soupe à l’oignon gratinée, and steak frites are offset by a revolving list of dynamic specials like moules meunière and côte de veau, all sumptuously paired with expertly selected wines.

These dishes can be enjoyed inside, where the bistro has a cozy cottage vibe, or – better yet – in the restaurant’s idyllically charming garden with graceful arches, cobblestone pathways and rustically manicured flora and fauna. As you enjoy your meal with the sun dimming and the garden lights twinkling on your date, you’d be hard pressed to find a better seat in Chicago.

EL ideas (Douglas Park)

Of the many incredible tasting menus offered in the city, few have as much personality and panache as Chef Phillip Foss’s EL ideas. Rather than the traditionally stuffy and sterile environment usually associated when diners are dropping hundreds of dollars on a tasting menu, EL ideas’ space is open and airy. It feels more like a friend’s playfully chaotic kitchen (indeed every diner has a great view of the chefs in action) than a quiet and serious Michelin-starred dining room.

With classic 90s hip-hop playing at a decibel level that makes you want to open that third bottle of wine you brought (yes, EL ideas is BYOB), you will enjoy some of the most innovative and outstanding cooking in the country, let alone Chicago. Just cross your fingers that Chef Foss’s iconic “French fries and ice cream” dish – a mind twisting play on sweet and savory flavors that shouldn’t work but might just be the best thing you’ve ever tasted – never leaves the menu.

Where to Drink

Vol. 39 (The Loop)

We all have friends that are experts in things: the guy for book recommendations; the sports fanatic; the guy for home renovations; the guy who knows his way around a bar. Luckily enough for me, my go-to for that last friend in question not only knows the way around a bar, but pretty much any bar, seeing as he’s logged countless hours leading some of the best bars in the city of Chicago. He’s the one who introduced me to Vol. 39, a bar without any trendy hype and yet with a bar program and a space that might be my single favorite watering hole in the city.

Vol. 39 is like that incredible person in your life that seems just perfect in everything they do – and yet also the nicest person you’ve ever met, without a shred of ego or self-centeredness. This bar just nails all the right notes without any pretentious fanfare.  Friendly, bow-tied-clad staff welcome you to a seeming conundrum of a room. With rich leather chairs and bookcases that are given freshness from gold accents throughout as well as the big, oversized windows that bring in the perfect golden hour sun it allows guests (given Vol. 39 is located on the third story) a front-and-center look at trains passing by on Chicago’s legendary “L” tracks.

But most importantly, whenever Luke (my friend who introduced me to Vol. 39) and I belly up to the bar with a mirrored backbar stretching to the ceiling, the summertime gin martini with a twist or winter Manhattan we inevitably start with is exquisitely prepared. It’s served just at the right temperature and finished far too easily. Here’s to Luke, Vol. 39, another round and more people and places like this.

Meadowlark (Logan Square)

Meadowlark is a bar with a bit (or – more accurately – significantly) more fanfare than Vol. 39, but for good reason. This bar is in the heart of one of the most culturally relevant neighborhoods in the city and, within a sea of dive bars and beer-and-a-shot joints, has created its own niche as elevated cocktail bar with a superbly executed avian theme. While Meadowlark didn’t create the themed-bar concept, they absolutely nail it.

Boasting a gorgeously produced cocktail menu (last time I was in, mine was titled “Field Guide Vol. 1) in which each drink is named after a different bird species. From the rum-based Mockingbird to the tequila-forward Prairie Warbler (and even a drink called Chicago Pigeon featuring Chicago’s notoriously acerbic Malört, which my fellow Chicagoans will recall with a shutter), all the drinks are delicious and unique.

The setting is posh with floor lamps, tufted sofas and tasteful bird art and all of this comes without the usual crowds and elbowing that are normal in this neighborhood. Meadowlark only allows as many guests inside as there are seats available, making this a perfect “nest” for your evening.

Galway Arms (Lincoln Park)

Chicago, as the de facto “capital” of the Midwest where the biggest beer brands in the country are located, of course features countless watering holes to grab a great pint. But few in the city pour “a pint of plain” like Galway Arms. And in a city that has the biggest St. Patrick’s Day celebration outside of Ireland, that’s a pretty important fact.

On the far too many days of the year where Chicago turns a cold shoulder and is wet, cloudy, snowing, freezing (or all of the above), Galway Arms is a warmly beckoning pub in the Lincoln Park neighborhood. It will make you forget about the weather as you enjoy some hearty fare and a pint (or two) of the black stuff served by a staff with authentic Irish accents. Best of all, Galway offers live Irish music four nights of the week, creating an experience that feels like you’re on the Emerald Isle itself rather than running away from Chicago’s windchill.

The Violet Hour (Wicker Park)

One of the best lines in all of bar literature comes from Bernard DeVoto’s The Hour. He’s describing that sublime point in the day where sowing turns to reaping. Where one’s day of productivity gives way to his cocktail ritual: “This is the violet hour, the hour of hush and wonder, when the affections glow and valor is reborn.” This bar is located in a building lacking any signage with the only identifier being the rotating street artwork. It pays fitting tribute to that beautiful line.

Widely known as the bar that put Chicago cocktail bars on the map and was started by the guys who did the same for New York City with Milk & Honey. The Violet Hour has maintained its crown as the city’s best cocktail bar despite stiff competition (see the two entries above) for sixteen years and counting.

A velvet-curtained entrance entreats guests to wait until the right table or bar seating is available, amplifying the experience that awaits ahead (and a Pavlovian trigger for any repeat visitors). Inside, it’s as if Devoto’s words of “hush”, “wonder” and “glow” manifest themselves in the bar through dim lighting, high-backed dark velvet seating, and soft-spoken patrons.

Any drink you order here will be outstanding, but if this is your first time, I implore you to order the now ubiquitous Paper Plane. It was here, within these walls, the modern classic cocktail was created for Violet Hour’s opening menu by none other than the king of modern classic cocktails himself, Sam Ross (of that NYC Milk & Honey crew).  With that bit of cocktail history to sip on, you’ll have plenty of time to think of what to order next.

Delilah’s (Lincoln Park)

Whiskey. There’s really only one reason to go to Delilah’s and that’s their absurd – by far the best in the city, but arguably up there with the best in the country – whiskey selection. At first glance, Delilah’s looks like any other dive bar, with sticky black floors, scratchy VHS tapes playing on a tube TV in the corner, and a graffitied bathroom. But with more whiskies to choose from than anywhere else I’ve been in my entire life.

In my profession in the bourbon business, that’s saying something but Delilah’s is a must for any whiskey fan, whether bourbon or Irish, single malt or Japanese. I won’t tell you what to order, just that I suggest you try something you’ve never had before (and keep changing it up every round). Oh, also don’t forget to pace yourself.

Where to Stay

Chicago Athletic Association (The Loop)

One visit to the Chicago Athletic Association’s second floor lobby – warmly dubbed The Drawing Room – and you’ll immediately understand why this is on the list. Impeccably restored within this over 100-year-old building, this grand room makes you feel like you’re in one of Europe’s centuries-old university libraries or some charming reading room straight out of Harry Potter. With dozens of seating areas interspersed among the room’s three fireplaces – plus long tables with warm tabletop lighting throughout – this room seamlessly blends the social and the productive.

It is just as appropriate for heads down focus time as it is for pre- (or post-) dinner libations. And The Drawing Room is just one of the five great spaces for food and drink throughout this historic landmark hotel (including Cindy’s, the hotel’s rooftop restaurant and bar with unparalleled views of the park, the skyline and Lake Michigan).

As a nod to its past life, the interior design throughout the hotel celebrates sport and competition. It includes pommel horse-inspired benches, tilework resembling vintage swimming pools and elevators featuring pristine basketball-like floorboards.

The Hoxton (West Loop)

A bit further west, the Hoxton has charm of the more modern variety. What it lacks in heritage against the Chicago Athletic Association, it makes up for in its fresh, contemporary vibes in the heart of the city’s trendiest – and most gastronomically inclined – neighborhood. Gorgeously designed with a mid-century modern aesthetic (think emerald green and rich cherry wood), the Hoxton is no stranger to great options for food and drink itself.

It features Cabra, its Peruvian rooftop restaurant, and Lazy Bird, its plush, swanky cocktail bar on the lower level where you just feel classier and cooler by association (fair warning: lines form early here). Given its location, though, you’d be remiss not to venture out for some culinary adventures, whether for the almost-too-good-to-be-true burger from Au Cheval; the two-Michelin-starred tasting menu at Oriole; or the damn good sammies from J.P. Graziano (you’ve seen The Beef, right?).

Knowing the Hoxton’s penchant for attention-to-detail and hospitality, I’m sure the beds are dreamlike and the pillows flawless – but, in a location like the Hoxton’s, promise me to spend as much time out of your room as possible.

Airbnb (77 neighborhoods)

One of Chicago’s greatest strengths is its diversity of cultures represented across its 77 neighborhoods, each one with a unique vibe and experience. And one of the best ways to get to know the city best is to find a great Airbnb in one of these colorful neighborhoods to experience it like a local.

With few exceptions, each neighborhood will bring something special to the table, but there are a handful of tips I can offer to help find which one is right for you. Many neighborhoods specialize in certain cuisines from around the world like Pilsen (Mexican), Rogers Park (Indian), and Chinatown (obvious), so if you’re keen for some authentic food, the city’s neighborhoods won’t steer you wrong.  I also suggest picking an Airbnb in a neighborhood close to an “L” station which not only will enable efficient travel during your stay but also puts you closer to culture and community since the stations serve as natural magnets for bringing people together.

Lastly, seasonality – and your preparedness (or lack thereof) – will make-or-break your time in Chicago.  If you’re visiting in the warmer months, I suggest finding something with some outdoor space so you’re not cooped up inside during the few months in Chicago when it’s warm.  Visiting during one of Chicago’s notoriously painful winters? Do yourself a favor and spring for something with a fireplace.

What to Do

The Art Institute of Chicago

A well-traveled friend of mine (and a New Yorker no less) recently visited the Art Institute of Chicago for the first time and said it just might be her favorite museum in the country. High praise, certainly, but by no means a surprise.

It boasts a permanent collection featuring some of the most culturally iconic art pieces from the past century – including A Sunday on La Grande Jatte by Seurat, Nighthawks by Hopper, Two Sisters (on the Terrace) by Renoir, and The Old Guitarist by Picasso (to name but just a few). Each room of the Art Institute feels like it contains some incredible masterpiece.

And amidst such art on the walls, you could be forgiven for overlooking the stunning work of art that is the Art Institute’s building itself. As you ascend the front steps, you’re greeted by what I like to call Chicago’s mascots: two enormous bronze lion statues regally standing guard night and day over Chicago, personifying the city’s strength, grit, beauty, and stoicism.

Once inside, the grand, wraparound staircase will sweep you up to the galleries waiting above. Impressively, the building only became more beautiful when the Modern Wing was added in 2009 in a way that was seamless both with the original structure’s Beaux Arts style as well as the surrounding city blocks.

Its 100-yard rising ramp from the park across the street and over Monroe Ave to the Modern Wing’s second level is a tacit invitation for passerby to stop inside; its floor to ceiling windows a lens through which the city’s skyline becomes another work of art itself to admire.

Architectural Boat Tours

This is my number one recommendation for any visitor, bar none, and that’s all due to the versatility of the experience. I’ve yet to find a single person – from a barely-three-year-old all the way up to an aging septuagenarian – who didn’t love their trip on one of Chicago’s architectural boat cruises.

Whether you’re the biggest architecture junky interested in learning something new from the incredibly informed and charming tour guides or just some teeny bopper looking for good TikTok content amidst the gleaming buildings and gritty bridges, you’ll have a blast on this “cruise.”

It simply traverses the calm waters of the Chicago River’s North, South and East branches, giving you unparalleled views of the city’s awe-inspiring and diverse skyline. For a city that introduced the skyscraper to the world (and still boasts home to some of the world’s greatest architecture firms), the award-winning tours should come as no surprise. What will shock you, though, is how much you enjoy the experience.

Cub’s Game at Wrigley Field

To me, one of the best moments you can experience in Chicago is a day game at Wrigley Field in the dead of summer, hot dog (Chicago-style, of course) in one hand and an ice-cold 20-ounce Old Style in the other. And while the Cubs haven’t been the most thrilling team to watch since they broke their dry spell and won the World Series in 2015, the park will make you care less about the (still hand-operated) scoreboard.

As the second oldest stadium in the Major Leagues, Wrigley retains that charm of yesteryear stadiums with soft sloping aisles and low hung upper decks, the kind you generally only see in very old baseball footage.

Unlike Fenway (the oldest park in the Majors), though, Wrigley has a symmetrical, calming beauty to it with its gorgeously ivied brick walls, the bell-curved shape of the bleachers, and the city’s Lake View neighborhood in the distance. It truly feels like the Vatican of Baseball (even if the Cubs’ standings are less than godlike).

Live Music

Thalia Hall. The Empty Bottle. Kingston Mines. The Hideout. These are just a small sampling of some of the best joints to catch live music in Chicago, where the city’s cultural vibrancy directly translates to a plethora of live music options spanning every genre you could imagine.

From rock to rap, folk to country, blues to jazz, and everything in between, Chicago will have a venue for you (usually with some interesting back history, like the 116-year-old Green Mill jazz club where Al Capone was a regular).

The Lakefront

I was recently reminded how much I, as a born-and-raised Chicagoan, take the lake for granted.  My friend and I were enjoying the view of Lake Michigan and he remarked how incredible it was that the lake felt more like a coast – its vast horizon and view as far as the eye could see – than a body of freshwater where you can see the other shore. While the lake doesn’t have tides or the salty sea air provided by the Atlantic or the Pacific, it does serve as Chicago’s muse.

With over 28 miles of shoreline and beaches bordering the city, the lake offers Chicagoans from every walk of life ample opportunity for leisure, reflection, exercise and enjoyment. Most notable of all, the lake is a pedestal for the city’s iconic skyline, mirroring its silhouette on calm days and, in many ways, symbolically watering the skyscrapers into the towering behemoths that keep careful watch over the city and its inhabitants every day.

The Bottom Line

There’s no way a single article from one person’s point of view could ever capture the full magic and essence of a city as vibrant, rich, and eclectic as Chicago. But I promise that if any of the points of interest here in any way piqued your curiosity, then Chicago will be your kind of town, too.

Far from being exhaustive, this guide is simply the tip of the iceberg – an amuse-bouche, if you will – for the truly thrilling and eye-opening joy the city offers with its fabric of diverse cultures offered from its hearty and welcoming Midwestern open arms. Come for a drink, enjoy a meal, stay for a lifetime. Regardless:

I bet your bottom dollar you’ll have some fun in Chicago.