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.

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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.

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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For watching athletes of the dancing variety, Chicago’s Auditorium Theater is a must

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?

Photo: Christian DeKnock

Photo: Christian DeKnock

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What 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.

Photo: Josh Hild

Photo: Josh Hild

Where to eat in Chicago

When it comes to fine dining in Chicago, there’s one name that stands out above the rest – Oriole. Laying claim to two much-coveted Michelin stars, the tasting-only menu is less a meal and more an experience to the savoured as long as possible. With just 28 covers, the cosy yet chic front of house sits beside the open kitchen where the artistically exquisite and mouth-watering plates, including the likes of enoki mushrooms with black truffle, and Wagyu beef with bone marrow butterscotch, are created with a flourish of confidence. For a taste of the orient head instead for the tasting and a la carte menus of Jeong (pronounced ‘chung’), which developed out of a neighbourhood Korean street food stall. Despite, or perhaps because of, its humble beginnings, the dishes are a sumptuous blend of peninsula favourites and extraordinary flavours that will have your taste buds singing.

Still as fresh as the day it opened some twenty years ago, Lula Café has a special place in the hearts of many Chicago residents thanks to its ability to feel both like a place for special occasions and somewhere to enjoy a midweek brunch. Proudly listing its string of local suppliers, Lula has also been doing the whole farm to table thing long before it was a thing – demonstrated best with the Monday night three-course Farm Dinners. Also working closely with nearby farmers is Smyth + The Loyalist. The ‘+’ here is important, denoting two restaurants under one roof, poetically run by husband and wife team John and Karen Shields. Head upstairs to Smyth for a traditional restaurant experience, or the grungier basement level Loyalist for some of the best burgers in town. However, for the ultimate in New American gastropubs, you should check out Giant, whose chefs dish out old (onion rings, pecan smoked baby back ribs) and sure-to-be new favourites (tempura sweet potato, Jonah crab salad with waffle fries) with unexpected skill and savour faire.

Giant Restaurant | Photo: Annie Hamnett

Giant Restaurant | Photo: Annie Hamnett

For your fill of Mexican cuisine, it’s hard to better Mi Tocaya Antojería, a few doors from Giant on Logan Square. The colour filled interior provides the perfect backdrop for chef Diana Davila’s zingy creations, ranging from tacos to lesser-known regional specialities harking back to her heritage south of the border, such as the lobster esquites. If there’s an all-American version of Mi Tocaya in Chicago it’s the bistro-stylings of Cellar Door Provisions. The crowds are drawn here by the freshly-baked breads, pastries, and cakes, though well-priced bring-your-own menus (incorporating plenty of that bread) run after dark a couple of times a week. And then there’s S.K.Y., a contemporary Asian-American fusion restaurant by up-and-coming chef patron Stephen Gillanders. The well-versed staff will guide you through the menu (the maitake mushroom and goats cheese salad is lovingly spoken of), or take the easy route and opt for the tasting menu to sample everything from white shrimp ceviche to Korean-inspired foie gras bibimbap.

Cellar Door Provisions

Cellar Door Provisions

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Located in the Wicker Park neighbourhood, the new Adidas 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

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Rooftop Sidetrack Chicago is known for its huge nightly events, bringing drag nights, show tune sing-a-longs and affordable drinks to a diverse, largely shirtless LGBT+ crowd

Chicago nightlife

Chicago has a host of excellent cocktail bars, though Kumiko throws a Japanese twist into the mix. The airy interior of this crossover between bar and restaurant (with lighter bites during daylight hours and full menu from 5 pm) adds the Japanese ability to surprise to traditional drinks, so expect your Manhattan to come with Kamoizumi Umeshu sake or your Old Fashioned to be mixed with traditional Japanese whisky. Gay bar Wang’s has similar bar-restaurant vibes, though with a greater emphasis on laid-back sociability, as emphasised by the interior’s bohemian décor, meaning there’s nowhere else like it in the city.

Taking its inspiration from the works of Toulouse-Lautrec, Marty’s Martini Bar is also a lot of fun. Catering to a mix of after-work locals and an increasingly gay crowd as the night moves on, the cocktails are perfectly made, service excellent, and outdoor terrace a nice surprise too. Sitting within the confines of the Kimpton Gray Hotel actually plays to the strengths of Vol.39’s decadent 40s-style spaces of soft leather, atmospheric lighting, and gleaming chromium. Given the old-fashioned ambience, you might not be surprised that the Old Fashioned is Vol.39’s signature drink, with up to eight varieties on the bar menu. Meanwhile, Apogee Lounge, on the twenty-sixth floor of the Dana Hotel and Spa boasts the second-highest rooftop bar in the city and magnificent views from the floor-to-ceiling windows. Really, though, the reason to come to Apogee is for cocktails, with drinks made with Michelin-star meticulousness using the very best ingredients, without the hugely extravagant price tag. Bear in mind though that Apogee is only open on the weekend and making a reservation for sundown is the smart thing to do. Heading there later is another option, as the bar slowly morphs into nightclub mode and the crowd gets dancing.

Photo: Malcolm Lightbody

Photo: Malcolm Lightbody

Rooftop Sidetrack Chicago is actually best-known for its huge nightly events spread across eight storefronts and 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 cosier bar, you can do worse than head to The Drifter, located in the basement of the Green Door Tavern, where there are real-life vintage vibes all round, and the occasional low-key belly dancing performance to boot. The Drifter offers an incredible selection of cocktails, rotating each night depending on which tarot cards owner Liz Pearce draws out of the pack, so fingers crossed for the velvety Chocolate Negroni and the intriguingly-named South American Mistress.

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.

Photo: Mohamadreza Azhdari

Photo: Mohamadreza Azhdari

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