Lynn Osmond has lived in Chicago for close to 30 years, but the St. Catharines, Ont., native, who oversees tourism in the Illinois city, has a unique perspective on how Canadians view her adopted home – and what many of us are missing when it comes to awareness and knowledge of the bustling midwestern destination.

“The Al Capone days are a long time behind us, but that’s still people’s picture of what Chicago is – rather than a gorgeous city on the lake,” she laughs.

“We’ve got a river that runs through us with this amazing River Walk, and we have a fabulous lake front that is free and clear with miles of parks where you can ride your bike and hike.”

She adds, “I’ve hosted many a mayor down here and they’re very jealous.”

And then there’s the famed misnomer for Chicago, the “Windy City,” which Osmond points out isn’t any windier, nor the weather worse in general, than many other places, including Toronto. She explains that the nickname was actually coined in the past to describe Chi-town’s blustery politicians.

A year ago, Osmond took over as the first female president and CEO of Choose Chicago after holding the same title at the Chicago Architecture Centre for a quarter of a century.

So, it’s no surprise that she is also quick to highlight Chicago’s special architectural heritage, prompting its title, “the Architectural Capital of North America.”

Recognized as the home of the skyscraper – The Home Insurance Company’s building on the corner of LaSalle and Adams Street is considered world’s first tall building constructed with an internal frame when built in 1885 – the city continues to boast some of the tallest buildings in North America.

“We’ve got a fantastic skyline,” Osmond enthuses, adding, “We just have some beautiful buildings. And we continue to build wonderful buildings, but we have a great legacy from the buildings of the 1920s – we kept them; (and) we have this great art deco period.”

Similar in nature to New York, she notes, however, that Chicago’s buildings are spaced further apart, meaning, “You can see things (here). Between the river and the lakefront, you really get view corridors in the city.”

And the best way to experience it, she adds, is on the water – specifically on one the city’s popular river cruises, where visitors can “sit on a boat for 90 minutes and go through this canyon of phenomenal buildings and look up and see this great architecture. It’s just a great way to float through the city and see these towers that go back to the early 1920s, and up to the current day.”

Such as the St. Regis Chicago, which became the third tallest building in the city when completed in 2020 and is the tallest structure in the world built by a woman – Jeanne Gang.

Beyond its marvellous buildings, the city’s tourism CEO cites fabulous museums, vibrant theatre and cultural institutions, great sports (including two baseball teams, one playing at historic Wrigley Field), and fabulous restaurants, which include 23 Michelin-starred restaurants and 55 Bib Gourmands.

There’s also the River Walk, a 2-km. long public space filled with restaurants, bars, cafés, parks, view corridors, and where people can rent a boat or kayak. “It’s just a lovely way to enjoy the riverscape and it’s one of the great tourist attractions,” Osmond says.

Meanwhile, there’s no shortage of current and future developments planned for the midwestern city that are certain to keep Chicago’s fire stoked:

A short list includes:

• St. Regis Chicago: The latest of downtown Chicago’s 151 hotels, the 101-story St. Regis Chicago has already changed Chicago’s famous skyline. The tower’s crystalline form was inspired by the facets of a shimmering gem and the building is coated in six varying shades of blue-green glass to reflect the changing colours of Lake Michigan.

Now expected to open May 1, the ultra luxury hotel will comprise the first 11 floors of the building, featuring 192 guest rooms, multiple signature dining options, a world class St. Regis Spa, indoor pool, and outdoor sunken terrace with scenic views. The hotel’s backyard is a 2.4-hectare botanical green space featuring a children’s play park and attractive ornamental and water gardens

• NASCAR Chicago Street Race: For the first time, NASCAR will roar into Chicago on July 1-2 for the first street race in its 75-year history, which will take competitors past and through many of the city’s downtown landmarks from the start-finish line near Buckingham Fountain. The Cup Series will be part of a one-of-a-kind sports and entertainment festival featuring concerts with bands such as The Black Crowes over the Fourth of July Weekend.

• Obama Center: Once complete, the Obama Center will serve as a marquee destination in Jackson Park, the former president’s home neighbourhood. More than a presidential library, the Centre will hold his archives and chronicle the legacy of America’s first Black president, but also to contribute to and transform the local community. Along with extensive landscaped gardens, the Centre is slated to open in 2025.

With so much to recommend it, Chicago certainly rates with the domestic US audience, having been named the #1 Best City in the US” by the readers of Condé Nast Traveler in 2022 for a record sixth consecutive time.

However, Osmond believes there’s a lot that Canadians still don’t know the city.

Describing it as a “kinder, gentler” New York, she says Chicago is a cleaner (due to its system of alleys behind buildings), a walkable city that similarly has “amazing shopping, wonderful restaurants, incredible culture, eight sports teams…” and 77 unique neighbourhoods to explore, including large Hispanic and gay villages, Little Italy and the largest Polish population outside Warsaw (including attendant culinary highlights, from famous deep-dish pizza to Polish perogies and paczki donuts, and her favourite, Ethiopian cuisine).

Accessible from Toronto by a 90-minute flight with Air Canada, United, or Porter, or via an eight-hour drive, Chicago makes for an ideal getaway for Canadians, Osmond says.

Direct flights are also available from Montreal and Vancouver. And a host of top Canadian tour operators with product into the city include Air Canada Vacations, Porter Escapes, Group Voyages Québec, NHG Tours, and Toundra Voyages.

Pressed for a top five must-do liar for Canadians visitors, Osmond says:

• Do the architecture river cruise
• Go to a free concert in Millennium Park
• Bike the lakefront
• Visit one of the city’s great cultural institutions, like the Art Institute
• Go up to the top of one of the tall buildings for a panoramic view of the city and Lake Michigan.

And, she smiles, “I’m going to give you six: Experience the cuisine of the city. Eat your way through!”