First experiences are usually what we connect with youth. But for my 83-year-old mother and me, a recent visit to the Windy City was our first.

Chicago had long beckoned to me. Here in Toronto, high rises are monstrosities. But in Chicago, gazing up at these tall rectangular buildings shooting upwards are about witnessing architectural dreams where the sky really is the limit.

Urban America can be overwhelming. And with a city the size and population of Chicago, a trip needs to be carefully crafted to capture its highlights.

Here are some recommendations for a weekend visit.

The best in stay. . . Langham Chicago

This luxury hotel was rated one of the best large city hotels in the United States by Travel & Leisure’s 2015 World’s Best Awards and for good reason. This modern Mies Van der Rohe IBM building is situated right downtown, with rooms that have floor-to-ceiling windows overlooking the Chicago River. The service here is impeccable. It has an award-winning spa. And my dinner at their second-floor restaurant Travelle was exceptional—it started with a grilled asparagus with Serrano ham and poached egg, followed by scallops with a vanilla-saffron emulsion, black garlic and chorizo. And solicitous service even included the loan of a pashmina wrap while I ate!

Access to the Langham’s Club floor lounge (for an additional $100 per person per day) includes a hot breakfast, afternoon tea with scones and clotted cream, and cocktails overlooking the Chicago River and Lake Michigan beyond.

Art and Architecture

So rapidly did Chicago develop in the late 1800s after the fire of 1871, both in population and wealth, that the answer to this development was to build upwards, With the invention of the elevator, buildings could be built above four stories and expand they did. The skyscraper was introduced in 1885.

You can’t help but walk through downtown Chicago and gaze upwards. Skyscrapers are everywhere. The Chicago Architecture Foundation offers many excellent tours, including the two-hour Historic Skyscrapers and 1.5-hour Evolution of the Skyscraper walking tours.

And of course, there is the well-reputed First Lady river cruise, which we took. Over 1.5 hours, our excellent docent Patricia Grund showed us many examples of the modern, post-modern, neo-classical and art deco buildings that surrounded us.

We also took the easily navigable “L” (or elevated) train out to Oak Park, a beautiful suburb of Chicago, where we enjoyed the one-hour Home and Studio Tour of the first home that Frank Lloyd Wright ever designed, at age 20, and where he lived with his family. Visitors can also get a 40-minute self-guided audio tour of other Frank Lloyd Wright houses in the area, or take a more comprehensive three-hour tour that includes both his Home and Studio and a tour of the neighbourhood.

The Art Institute of Chicago is another must. Tour its permanent collection of Impressionist art and view the special exhibit America After the Fall: Painting in the 1930s (on until September 18), with works by Edward Hopper, Georgia O’Keefe and Grant Wood, among others. For those with short attention spans, their Visitor Guide provides a list of what to see in an hour.

Urban Nature

Millennium Park is a 24.5-acre public park that was originally meant to celebrate the second millennium but wasn’t actually completed until four years later, in 2004. Check out the free summer concerts and other events at the Jay Pritzker Pavilion, designed by Frank Gehry. Look at your reflection in Cloud Gate (nicknamed The Bean), a 110-ton stainless steel structure that reflects the city’s skyline. Cool off in the Crown Fountain: its fountains emanate from the mouths of ordinary Chicago citizens whose faces are projected through video onto two 50-foot glass towers. And enjoy the birds and flowers as you wander through the beautiful paths in Lurie Garden, bordered by 15-foot high hedges.

The Riverwalk, on the south bank of the Chicago River, is a beautiful pedestrian walkway that connects downtown to the shores of Lake Michigan. Wander under its many bridges, feeling the breeze from the river. Stop for a cocktail at the outdoor Tiki Bar, or rent a bike or kayak to see the sites that way. You can also visit the McCormick Bridgehouse and Chicago River Museum : it’s well worth the $5 entry fee to view the gears that lift the moveable bridges, and for the great views and photo opps you’ll get five stories up.

With these great recommendations, you’re all set for a fun Chicago getaway with mum, grannie, sister or girlfriend!