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Windy City Weekend

More than just deep-dish pizza and hot dogs with no ketchup, Chicago can really tick all the right getaway boxes. Let me count the ways…
By Doug Wallace
It seems everybody wants to go hiking all of a sudden. Maybe the world’s problems are becoming too big to bear, but getting back to nature and tuning out seems to be all the rage. Don’t get me wrong, I love a good heart-pounding climb up a rainforest mountain, but there’s nothing like a decadent city escape to take you outside of yourself and “unquiet” the mind.
Fifty-seven million people visited Toronto’s sister city in 2018. Our partnership with Chicago began in the early 1990s, in part because we had a lot in common – both being big, international, cultural hubs propping up a Great Lake. And today, despite the exchange rate, a weekend in Chicago is pretty good value: Toronto’s downtown hotel rates are actually higher.
When I’m visiting a city for the first time, I do the touristy things and get them out of the way so I can skip them next time around. Not so in Chicago. I can never get enough of the Art Institute of Chicago or take too many pictures of my reflection in Cloud Gate, a.k.a. the “Bean.” And the Architecture River Cruise never gets tired, mostly because new buildings are popping up on the skyline here all the time (Chicago invented the skyscraper, after all). One of them, the new 150 North Riverside building, seems almost to defy physics. The Skyscraper Gallery at the newly opened Chicago Architecture Center exhibits scale models of famous buildings in Chicago and around the world in a 40-foot-tall space overlooking the river-cruise dock. Also, terrific fun is the Center’s interactive model of the city, which has been expanded to include 3,000 buildings, its film and light show highlighting the city’s history and distinct neighbourhoods.
Speaking of which, scoping out different ’hoods is one of the best ways to get under Chicago’s skin. Once you’ve combed through downtown, you can get the bigger picture by getting lost in other parts of town that may be unfamiliar to you. Neighbourhoods are also quieter, so you actually get in some relaxing, sans hustle and bustle. Some cities are just too big to explore otherwise; places like Tokyo and London have to be done section by section because biting off more than you can chew yields guaranteed choking. Thankfully, the elevated “L” train system is easy and efficient, albeit deafeningly loud.
We started a fun weekend far from the middle of town, checking into The Robey, a gem of a hotel built into a former Art Deco office tower in Wicker Park – perfect for the hipster in all of us. A retro vibe set the scene, carrying on way up to the rooftop bar and wraparound terrace, complete with a stunning view of downtown and an up-close look of the building’s spire. Cue the Instagram.
Wicker Park has its own little high-street shopping bit, with little eateries scattered throughout. Vintage-wear worshippers scour the second-hand stores here and then stick around for tacos afterward. We went for a long walk along The 606, elevated parkland on what was once the Bloomingdale rail line, its story similar to that of New York’s High Line. When the sun sets, the nearby Logan Square area is scattered with countless bars and clubs, including the classic-cocktail bars Pink Squirrel (a bar and bowling alley named after a 1950s drink of the same name) and Spilt Milk (housed in what was an apothecary in the 1920s). Seriously, they make it so easy to get into trouble here.
One thing you have to watch out for in Chicago are the diagonal intersections, where three streets create six corners. My partner, bless him, headed the wrong way down the wrong street one night and was more than an hour late for dinner. I think I drank a whole bottle of pink bubbles waiting for him. (“Meet you there!” now takes on a whole new shadow of doubt, sadly.)
Orgasmic food moments? Plenty. Chicago is well-known for its culinary adventures – thick pizzas and ketchup-less hotdogs aside. There’s a ton of great Italian food, thanks to the town’s rich, 100-year Italian history. We ate our way through the menu at Siena Tavern, a cavernous, made-from-scratch kind of place, all rustic and raucous. At Coda di Volpe, we cut our way into pizza with shears, also devouring house-made pasta and a crudo I wanted to crawl into. This neighbourhood spot is up near Wrigley Field, an area that’s now reinventing itself: the dingy watering holes are being replaced with cool eateries, and rib joints are springing up among the city’s dozen or so comedy clubs that also cluster here for some reason.
You will no doubt already be more familiar with the part of town just a few blocks east: Boystown ring a bell? We sampled the elixirs at Elixir before ogling the muscles on the rooftop at Sidetrack, finishing up on the dance floor with the kids at Scarlet Bar. When I say it’s gay night, I mean it.
The next day, back downtown for one last hurrah, we finished our bourbon-soaked weekend by sharing a gallon-size rum cocktail that resembled an octopus with our friends at Three Dashes and a Dot. Where else in the world can you stumble into a basement tiki bar that’s packed on a Sunday night at 6 pm? Nowhere else, that’s where.

Roundup of Chicago hotels
There are a surprising number of new or newish hotels cropping up in Chicago, many of them opening in elegant, refurbished landmark buildings.
The Robey took over a 1929 Art Deco office building in Wicker Park, a one-minute walk from the L Blue Line (the one to and from O’Hare). The rooms are modern and sparse, still carrying a torch for the building’s former life. Cocktails in the UP Room on the 13th floor will net you a 180-degree view of downtown – and a mean Old Fashioned.
Hotel Zachary is across the street from Wrigley Field. Rooms are a mix of contemporary and traditional, modern lighting and local art mixed with pinstripes and wingback chairs. The Zachary is a great home base for sports fans, comedy fans (all the top clubs are here) and gay-bar fans – Boystown is a convenient five-minute walk away.
Moxy Chicago Downtown does form and function extremely well in the River North area, a short walk from Magnificent Mile. This is a sink-by-the-bed, pegs-for-your-clothes kind of place, but it’s extremely well designed. The lobby is like a colourful clubhouse, filled with art, games, a 24-hour taco counter, a coffee bar and a bar.
Found Chicago is also in the River North area, part of a chain whose charm lies in its budget-friendly quirkiness. Both private and dorm-style rooms are simple and sparse, but fun and snug. Public spaces are a blaze of colour, the furnishings and objects
culminating in a 1970s rumpus-room look. Be sure to check out the Asian-inspired bar and lounge.
The Hotel at Midtown in Bucktown is a fitness oasis, a “sports resort,” part of the Midtown Athletic Club. Rooms are minimal and masculine, all hardwood flooring, toffee leather chairs and dark wood headboards. Guests can get in on the tennis, boxing, spinning, aquatics, golf simulators, even yoga on the roof at sunrise. There’s a spa, too.
St. Jane Chicago opened recently in what was a Hard Rock Hotel in the Carbide & Carbon Building, another Deco landmark. Rooms have a feel for the past, with a pink-and-taupe colour palette, black leather chairs, gold accents, and marble bathrooms – all very 1930s. Guests on the lavishly decorated top-floor rooms have access to a private rooftop bar.
Hotel Julian, located in what was once the Atlantic Bank Building, was named for the patron saint of travellers. You’ll find high ceilings, nice linens, leather headboards, elegant armoires and black-and-white bathrooms. Public areas are playful and cozy. The steak-forward gastropub About Last Knife is worth it just for the name.

DOUG WALLACE is the editor and publisher of travel resource TravelRight.Today.

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