Chicago Travel Guide

Chicago Travel Guide

A friendly bunch of craft beer brewers living across a city of 77 neighbourhoods crammed with cutting-edge architecture, world-class cuisine and classy Lake Michigan shores, the people of Chicago really could be more smug. Circumnavigate the vibrant Loop of downtown Chicago or walk straight along the affluent Gold Coast to discover just what the locals are keeping humble about; as well as swanky retail revelry on all sides, you’ll discover a chilled out bar culture and a nightlife scene to remember, particularly for LGBT partygoers. With a solid reputation as one of the most inclusive LGBTQ+ communities in the US, Chicago is a city for all. Boystown, in particular, with its fine array of after-hours entertainment, decadent spas and boutiques, not to mention the upcoming Andersonville, famed for its Swedish Heritage and gay-friendly atmosphere. Whether it’s a Pride Parade, Dyke March or any other summer street festival you’re after, Chicago can satisfy your hedonistic cravings (as well as those for definitive Deep Dish Pizza). Read on for more of what to do in Chicago, with Mr Hudson’s trusty Chicago gay travel guide.

The best hotels in Chicago

Let’s start this gay Chicago travel guide with a roundup of the best places to stay in Chicago. An oh so very proper, British welcome is waiting for guests within The Langham, a glittering luxury hotel situated in a Mies van der Rohe-designed skyscraper overlooking the city and Lake Michigan. Up the posh ante at the Langham by upgrading to the hotel’s Club level where stunning views are served along with a buffet breakfast, afternoon tea and premium libations and where dedicated butlers make check in and check out a wholly civilized affair.

Once reserved for a privileged few, the Chicago Athletic Association – a mainstay of posh, mid-western elite for 122 years, has blissfully opened its doors to all. This downtown destination on the doorstep of Millennium Park is one of the city’s swankiest hotspots housed in a landmark building and ‘sporting’ everything from a rooftop bar to unique dining options and gaming rooms to elegant guest rooms replete with vintage athletic gear.

At The James, you can exponentially expand your art appreciation thanks to the hotel’s art program featuring work by both prominent and up and coming artists. If conquering the Magnificent Mile has left you bone weary, let the trials and tribulations of a day spent power shopping vanish courtesy of blissful ministrations delivered by the ASHA Spa. Other signature services for James guests include a 2500sf, full-service gym and classes at Yoga Loft Chicago to ensure you look as good as you feel when you slip into those new, designer jeans.

Where it sits tucked into its exclusive, Gold Coast neighbourhood; the Viceroy is a standout among a bevvy of neighbouring, historic mansions just steps from the Magnificent Mile and Lake Michigan. A celebration of locally-inspired luxury, the Viceroy melds cutting-edge luxury with ageless elegance across its 180 guestrooms and suites.  Whether you’re staying the night or simply passing through, while at the Viceroy you’d be remiss not to have your martini shaken at Devereaux where breathtaking views and poolside plates are the perfect accoutrement to a cocktail and a decidedly chic way to help start your evening… or end your night.

Elegantly residential, The Thompson Hotel is tucked away in the toniest of the Gold Coast enclave; just minutes to the lakeshore and steps away from chic dining, theatre and the Lincoln Park Zoo. With newly designed interiors by Tara Bernerd, the Thompson is an elevated, mid-century-inspired beauty featuring spacious rooms and a drop-dead gorgeous, dual level penthouse loft that’s nothing less than sigh-worthy.

The Langham

The Langham

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Recommended hotels in Chicago
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DISCO is well-equipped with all the necessities one might need to ignite a disco inferno

Things to do in Chicago

If you’ve seen the movie Ferris Bueller’s Day Off (and we know you have), you know that you don’t have to be a sports fan to revel in a day at Wrigley Field. Between roving carts hawking a spicy elixir known to locals as Uncle Dougie’s Bloody Marys and a ten dog menu celebrating hot dogs through the decades at Decade Dogs near section 123 at Gate F, you don’t need much more reason to root, root, root for the home team.

For watching athletes of the dancing variety, Chicago’s Auditorium Theater is a must. Home of the Joffrey and frequent host to everyone from the Alvin Ailey American Dance Theater to David Gilmore; the Auditorium Theater is a national landmark that has welcomed presidents and superstars, opera divas and rock and rollers to its hallowed stage for more than 125 years. Even if you don’t make a performance, a visit to tour the Dankmar Adler/Louis Sullivan designed marvel with the house historian is worth the trip.

One place you will have the same experience over and over again is the Art Institute of Chicago where a permanent collection of iconic masterworks by Dalí, Magritte, Van Gogh, Seurat and Grant Wood makes this museum something akin to your favourite coffee table book come to life. At AIC, even the architecture is part of the fun, ‘Zero Gravity’ in the Modern Wing, anyone?

Auditorium Theater | Photo: Gina Samarotto

Auditorium Theater | Photo: Gina Samarotto

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Things to see in Chicago

While the lake is one of the most popular Chicago sightseeing destinations during the summer months, Millennium Park is the city’s four-season go-to for locals and tourists alike. Built on a site passionately protected by the Illinois Central Railroad for nearly 150 years, Millennium is now home to a collection of sculpture and architecture that makes it a part museum, part park but one hundred per cent heart in the centre of the city. While you’re there, don’t miss a walk through Lurie Garden. A five-acre homage to Chicago’s ‘Urbs in Horto’ motto, Lurie is a brilliantly designed oasis in the midst of Chicago’s concrete jungle.

When in Chicago, such proximity to the Magnificent Mile can’t help but result in some sort of shopping. While spending time in stores you already have access to might be alluring, take advantage of some heady, one-on-one boutique time. At J. Toor consultants will help you select fabrics and styles before meticulously taking more than forty, personal measurements and sending the information off to their London ateliers. The result? Six to eight weeks later, you’ll receive bespoke, utterly divine, made to measure clothes that fit like a glove. For the homebody abroad, few destinations trump the vintage emporium P.O.S.H. when it comes to home goods. From hotel silver to Limoges to dinnerware emblazoned with the motto ‘Pancakes Makes People Happy’ (well, they do), P.O.S.H. is a treasure trove of previously loved ‘must haves’ on North State Street.

P.O.S.H.

P.O.S.H.

Millennium Park | Photo: Gina Samarotto

Millennium Park | Photo: Gina Samarotto

Where to eat in Chicago

Imagine you’re at a table where dinner looks like an Asian inspired still life and desert is a green apple infused balloon that floats above your head. No, you’re not behind the scene at Cirque du Soleil… you’re at Alinea, Grant Achatz’s Chicago-based temple to gastronomic phenomenon. Over the years, Alinea has made itself a staple of the Chicago food scene and deserves the distinction to this day.

Also by Achatz is the well-lauded Aviary – a new gem in the Alinea Group crown where gourmand delights are brought to life by Executive Chef Dan Perretta. Driven by a passion for escalated dining (not to mention a notably distinctive cocktail menu); guests may indulge in any of Perretta’s small bites, shareable plates or the life-changing, seven-course food and cocktail menu served inside the kitchen at Aviary’s covetable tasting table.

Chicago native Stephanie Izard is no stranger to food. Izard has helmed the burners at some of the Midwest’s most acclaimed kitchens (including Jean-Georges Vongerichten’s now-defunct Vong) before opening her first restaurant a little over a decade ago. Today, she is the cyclonic force behind Girl & The Goat, home to some of Chicago’s most covetable tables. With dishes including wood oven roasted pig face and duck tongue on the menu, Girl & The Goat can’t help but command some attention from Chicago bound gourmands.

Aviary

Aviary

One would think it would be difficult at best to compete for attention in a town so rife with brazenly cutting-edge offerings; but Chicago does just that with avec, a Mediterranean meets Midwestern eatery where shared plates and a notable wine list – more than thirty are available by the glass and over one hundred and thirty make up the restaurant’s impressive cellar – have made the minimalist, wood clad eatery on West Randolph a singular sensation.

Last by not least, Roister’s is where you’ll want to head to satisfy an urge for vibrant flavour. Rooted in ‘primal cooking techniques combined with modern technology’, a meal at Roister’s is like sitting down in a friend’s kitchen – assuming of course that your friend also happens to be a cooking wunderkind specializing in exponentially elevated comfort food. What’s more, the restaurant has a delivery menu that brings exquisite satisfaction readily to your doorstep – hello, “Netflix & chill” night.

Girl & the Goat

Girl & the Goat

avec | Photo: Derek Richmond

avec | Photo: Derek Richmond

Fans of throwback sportswear will love what the Adidas Originals Flagship Store is up to. Located in the Wicker Park neighbourhood, this new flagship store covers a space of almost 5,000 square feet

Shopping in Chicago

When in Chicago, such proximity to the Magnificent Mile makes a shopping spree an absolute must. As well as the usual chain stores and mega malls, there are more than quite a few one-off gems to be found. The Gallery Aesthete, for example, is a neat combination of menswear boutique and art gallery in a sleek space that showcases cutting-edge fashion alongside art with a focus on design. The city’s artistic streak continues at Rotofugi, a geeky knick-knack store with an art gallery out back. Rotofugi is recommended as the perfect place to pick up a niche gift or pop culture collectable, before browsing the store’s series of eclectic artworks.

Fans of throwback sportswear will love what the Adidas Originals Flagship Store is up to. Located in the Wicker Park neighbourhood, this new flagship store covers a space of almost 5,000 square feet, revitalising the local community and bringing creative talent to the area. Inside the store itself, you’ll find customized art pieces and installations created by hometown heroes Tubsz and POSE. Adidas, with the idea of showcasing local rising stars and artists, are working with non-profit iPaintMyMind to enliven the space with new design and live events. For its launch event, the store even hosted exclusive performances from the likes of BJ the Chicago Kid and DJ ELZ.

Those in search of a quality, made-to-measure suit without the scandalous price tag should try out Alton Lane on Oak Street. Interested buyers can book an appointment with a style expert who will measure and advise on various custom design options. They know what they’re talking about too! Stock Mfg. Co., our next store, started off as an online menswear retailer but has since blossomed into a unique shopping concept where everyday collections share floor space with the on-site factory beside a lounge space with beer on tap. Not only are the clothes unfussy and affordable, but the added bonus of a round of pool and a cold one makes this a store worthy of our attention.

Photo: Jacob Blankenship

Photo: Jacob Blankenship

Another worthy Wicker Park store is Asrai Garden, a florist and lifestyle store that brings together dazzling accessories with fragrant blooms. Not your usual flower store, the ambience here is decidedly quirky, with antelope heads on the dark walls and tarot cards and incense being sold alongside asymmetric flower arrangements. Keeping it unconventional is infamous music store Dusty Groove, named as one of the best record stores in the US by Rolling Stone for its eclectic range of underground international artists and rare finds. From alternative hip hop and world music to African dancehall and everything in between, Dusty Groove’s vinyl collection has been curated from diverse tastes and obscure private collections, making it one of the most popular stores among DJs and record hounds. While in store the fanatical staff will help you find what you didn’t know you were looking for, but you can also browse online at home if you can’t get enough.

Photo: Maarten Van Den Heuvel

Photo: Maarten Van Den Heuvel

Photo: Austinc Neill

Photo: Austinc Neill

Chicago nightlife

Get high in Chicago at the Apogee Lounge, the second highest rooftop bar in Chicago on the 26th floor of the Dana Hotel and Spa (also one of the best Chicago points of interest in its own right!). Just two blocks on from the Magnificent Mile, Apogee Lounge is an upscale haven, featuring interior marble flooring and floor-to-ceiling windows leading outdoors onto a terrace area replete with sleek lounge sofas, a fire pit for cooler evenings and, of course, spectacular views over the whole of Chicago. Really, though, the reason to come to Apogee is for the cocktails. Served up in seashells and ornately shaped glass designs, the drinks themselves are made with Michelin-star meticulousness using the very best ingredients, without the hugely extravagant price tag. Bear in mind that Apogee is only open on the weekend and making a reservation for sundown is the smart thing to do. Heading there later is also an option, as the bar slowly morphs into nightclub mode and the crowd gets up to dance.

When you just can’t get enough rooftop cocktails, Sidetrack Chicago can provide that and much more. Not just a name on the lips of Chicagoans, this gay bar is famous throughout the country for its massive nightly events spread over eight storefronts on multiple levels, bringing drag nights, show tune sing-a-longs and affordable drinks to a diverse, largely shirtless LGBT crowd. When you’re in the mood for a cosy bar, head towards The Drifter, located in the basement of the Green Door Tavern, the site of a former speakeasy where much of the décor remains. Vintage vibes all round, with occasional low-key belly dancing performances, The Drifter offers an incredible selection of cocktails, rotating each night depending on which tarot cards owner Liz Pearce draws. We hope good fortune will allow you to taste the velvety Chocolate Negroni or the intriguingly named South American Mistress.

Photo: Malcolm Lightbody

Photo: Malcolm Lightbody

Another unique gay club for the books is Progress, where beautiful bartenders serve up craft beer in upscale environs to the sounds of various great DJs. At least one designer cocktail, while you’re here, is a must, before moving onto the dancefloor and busting moves beneath an impressive design installation made from over 19,000 lightbulbs. If pop art and 70s disco is more your thing, unleash your inner Travolta at DISCO, a gay club with a delicious disco vibe. Packed with 70s glamour, DISCO comes equipped with an LED illuminated dancefloor á la Saturday Night Fever, retro wall features, fur sofas and mirrored ceilings. Flair trousers and gold lamé optional, of course.

Right in the centre of Boystown it’s unlikely you’ll ever be short of gay club options, but Splash, in particular, is a winner for its eco-friendly ethos, strong drinks and on-point décor. Oozing friendly-but cool vibes throughout, choose from a chic spot in the lounge, pride of place at the bar or dance to your heart’s content in the centre of the club. In keeping with the wet theme is gay club Hydrate, the premiere spot in our Chicago gay nightlife guide for drag shows and late-night dance parties. Hydrate’s top of the range light and sound system complement the various talented DJs who play to euphoric crowds each night. Before raving it up, however, head down the Beauties & Beaus shows which on weekends features Chicago’s hottest male dancers alongside the best of the city’s drag queens until 5 am. If night-time action is not enough, come back on Sunday to check out Sunday Funday, a post-brunch party starring go-go dancers that starts at 2 pm.

DISCO

DISCO

DISCO

DISCO

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