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

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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

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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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