So when my friend Ryan suggests a tiki bar in downtown Chicago, I’m in.

When we finally find the door to the place, in a River North alley east of Clark Street lit by—what else—tiki torches, Three Dots and a Dash is packed to the tits, and it’s barely 6 p.m. And it’s Sunday.

THINGS TO DO: IN CHICAGO

This speakeasy-style traditional take on the tiki bar comes complete with low lighting, massive menus, cheeky ceramic glasses, top-notch rum and house-made elixirs. Cocktail classics are rooted in the past—the Tropical Itch, the Strip and Go Naked, the Pinky Gonzales (created by my friend Trader Vic in 1964) and the original Three Dots and a Dash cocktail invented by Trader Vic’s rival Don the Beachcomber in the late 1940s. Tiki bar trivia!

We settle on a group cocktail, the US$85 Bali Bali, a giant concoction of tropical fruit juices, rum, Armanac and gin. It looks like a sea monster overflowing with liquid nitrogen. It’s fine, meaning I don’t hate it and it goes right to our heads. My bar is low at the tiki bar.

Cocktail hour is rarely something to write home about, but we have our moments.

WHERE TO STAY: IN CHICAGO

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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 13^th floor will net you a 180-degree view of downtown—and a mean Old Fashioned. $ therobey.com

READ MORE ABOUT: THE ROBEY

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. $$ hotelzachary.com

THINGS TO DO: IN THE WINDY CITY

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 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 bar. $ moxychicago.com

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 get in on the tennis, boxing, spinning, aquatics, golf simulators, even yoga on the roof at sunrise. There’s a spa, too. $$$ midtownhotelchicago.com

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 objets culminating in a 1970s rumpus-room look. Be sure to check out the Asian-inspired bar and lounge. $ chicago.foundhotels.com

F&B: TIKI BAR ACTION

St. Jane Chicago opened in what was a Hard Rock Hotel in the Carbide & Carbon Building, another Art Deco landmark. Rooms have a feel for the past, with a pink and taupe colour palette, black leather chairs, gold accents, marble bathrooms, all very 1930s. $$$ stjanehotel.com-en.com

Hotel Julian, located in what was once the Atlantic Bank Building, this spot 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. $$ hoteljulianchicago.com

CHOOSECHICAGO.COM

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There’s nothing like a decadent city escape to take you outside of yourself and “unquiet” the mind. Toronto’s 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. Today, despite the exchange rate, a weekend in Chicago is pretty good value, primarily because the hotel room rates are relatively low, like, often under $200.

Do touristy things. One can never get enough of the Art Institute of Chicago or take too many pictures of one’s reflection in Cloud Gate, a.k.a. the “Bean.”

Ogle the big buildings. The Architecture River Cruise never gets tired either, mostly because new buildings are joining the skyline here all the time—Chicago invented the skyscraper, after all. The 150 North Riverside building seems to almost defy physics. The Skyscraper Gallery at the Chicago Architecture Center exhibits scale models of famous buildings in Chicago and around the world in a big space overlooking the river-cruise dock. Also terrific fun is the Center’s interactive model of the city, which now includes 3,000 buildings, its film and light show highlighting the city’s history and distinct neighbourhoods. This is very cool.

WHERE TO STAY: CHICAGO HOTEL ROUNDUP

Hit the ’hoods. Scoping out different parts of town is one of the best ways to get under the skin of Chicago. Once you’ve combed through downtown, getting lost elsewhere gives you the bigger picture. Neighbourhoods are also quieter, so you actually get some relaxing in sans hustle and bustle. Thankfully, the elevated “L” train system is easy and efficient, albeit deafeningly loud. Try Wicker Park, Bucktown, Ukrainian Village, the West Loop, Pilsen and Andersonville.

Go Italian. Chicago is well-known for its culinary adventures, thick pizzas and ketchupless hotdogs aside. There’s a ton of great Italian food, thanks to the town’s rich, 100-year Italian history. Eat your way through the menu at Siena Tavern, a cavernous, made-from-scratch kind of place, all rustic and raucous. At Coda di Volpe, you cut your pizza with shears and devour house-made pasta. This neighbourhood spot is up near Wrigley Field, an area reinventing itself, the dingy watering holes being replaced with cool eateries and rib joints springing up amongst the city’s dozen or so comedy clubs, also clustered here for some reason.

Drink up. When the sun sets, the Logan Square area is littered with countless bars and clubs, including 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 once a 1920s apothecary. Seriously, they make it so easy to get into trouble here.

F&B: TIKI BAR ACTION

When you go. One thing you have to watch out for in Chicago are the diagonal intersections, where three streets create six corners. Tim headed the wrong way down the wrong street and was more than an hour late for dinner one night. I drank a whole bottle of pink bubbles waiting for him. “Meet you there!” now takes on a whole new shadow of doubt, sadly.

CHOOSECHICAGO.COM

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A retro feel sets the scene right at the front desk and carries on 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.

Vibe: With its abundance of restaurants, lounges and private spaces, The Robey is a social hub. It honours its past with preserved Deco features (including bronze elevators) with minimalist Mid-Century touches at every turn, all gold metal trim and frosted glass.

Rooms: The 69 tower rooms feel like the former offices they once were, with that opaque wire glass, industrial colours, hardwood floors, simple furnishings. Big windows let in a ton of light, so motorized blackout drapes are very welcome. Twenty multi-bed Annex Loft rooms in an adjoining warehouse building from 1905 offer up industrial style and boutique finishes, perfect for families and the budget-conscious.

THINGS TO DO: IN CHICAGO
MORE CHICAGO HOTELS

F&B: Where to begin here. Café Robey on the main floor has a neighbourhood open-kitchen restaurant feel, doing American comfort food up extremely well. Have the duck hash for breakfast. We saw a man having bourbon for breakfast, but maybe don’t do that. A big, soothing lounge on the second floor is part work space, part bar. The indoor-outdoor Cabana Club on the 6^th floor is a hot weekend ticket, offering 180-degree views of town, a small food menu and a big cocktail list. And the UP Room is the 13^th-floor rooftop cocktail bar with exclusive access for guests at happy hour. The view is insane. So is the flight of mezcals.

Extras: Free bicycles! Free water and beers in the room.

Off-Site: 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. Go for a big 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 littered with action.

Rate: $$

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