How to do Toronto, Chicago-style

It takes exactly half a magazine and one glass of complimentary white wine (if you fly Porter Airlines) to skip over to Toronto for the weekend. And Chicago’s Canadian sister city is well worth a few days of exploration.

The perfect date night in Toronto

Looking for a genuine Toronto date night?


Stay at the Chelsea Hotel downtown. They’ll babysit the kids in the cute playroom—complete with organized activities and real bunnies—and park the teens at the lounge for arcade games, video games, pool tables and more.


Once they’re settled and having fun, you and your love can grab drinks at the hipster-esque Bar Raval in Little Italy and go salsa dancing at Lula Lounge in Dundas West for a truly festive night on the town.


Despite the currency exchange, which is presently in American favor—why hello, 30 percent sale on life—and those friendly Canadian accents, you’ll feel right at home in this urban scene don’tcha know.

In fact, Toronto and Chicago share so many similarities, getting around Canada’s largest city is a total lakeside breeze. Because if you love Chicago, chances are, you’ll love Toronto, too.

If you love Shedd Aquarium …

You’ll love Ripley’s Aquarium of Canada.

We are spoiled here in Chi-town with our world-class museum of fishy wonder. But Ripley’s has some attractions that rival even our beloved Shedd. With a whimsical play center for kids that includes touch tanks just their size and a moving walkway that glides right into the underbelly of overhead sharks—plus an entire exhibit devoted to jellyfish—this stop is a can’t-miss.

If you love the lakefront …

You’ll love Centre Island.

An adorable amusement park devoted to littles—Centreville Theme Park—is only one reason to make this spot a priority. Ferry boat rides, hiking and biking trails and overall outdoor beauty make for a perfect day to bask in the Canadian sunshine.

If you love the Field Museum …

You’ll love the Royal Ontario Museum.

Giant, impressive dinosaur skeleton at the entrance? Check. Enough exhibits to get lost in for hours with interactive kid zones? Check. Everything we Chicagoans love in our history museums can be found right here.

If you love the 360 Chicago or Skydeck Chicago …

You’ll love the CN Tower.

Because if you didn’t take a selfie on glass over the entire city, did it really even happen? Make sure to make a reservation to eat at the restaurant on top so you can have a rotating, 360-degree view as you munch. If you don’t order the Lindt’s chocolate ice cream for dessert, we’re not friends anymore.

If you love Green City Market …

You’ll love St. Lawrence Market.

Not only is it home to Toronto’s faaaamous sandwich, the Peameal Bacon, this market has rows of cute little stands with fresh foods, treats and souvenirs ripe for the picking. Looking for more local foodie favorites? Check out Bannock for authentic Canadian comfort food, freshly baked bannock bread and their famous chicken pot pie.

If you love Chicago’s neighborhoods …

You’ll love Little Italy, Dundas West and the Distillery District.

Not into the whole touristy thing? In true Chicago fashion, Toronto also has wonderfully colorful neighborhoods to explore. In Little Italy, you’ll find the hippest restaurants and nightlife. And in Dundas West, you can walk strings of art galleries, coffee shops and more. The Distillery District is a cobblestone paradise for antique and vintage shopping fanatics.

If you love the United Center …

You’ll love the Air Canada Centre.

This country is the bona fide home of hockey, and you’ll see their pride in the game everywhere you look—including at the Hockey Hall of Fame close by—so this arena is a giant attraction for locals and tourists alike. Catch a Maple Leafs or Raptors game during your stay, and join in on the hometown excitement.

If you love the Magnificent Mile …

You’ll love the Bloor-Yorkville shopping district.

It’s basically Michigan Avenue with the same stores and vibe, but with the exchange rate, everything is a great deal. Plus, you get to say you bought that leather jacket abroad, which basically means you’re winning at life.

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