Best things to do in Chicago

If you love baseball, historic buildings and hot dogs, this lakeside US metropolis is for you.

Chicago is often called the “Second City” or the “Windy City”, but its top-notch restaurants, waterfront location, sports history, and culture make it a first-rate US destination. 

The Midwestern city, which sits along Lake Michigan stretching north to south and culminating in a neighbourhood in the middle called The Loop, offers sandy beaches, great architecture, classic eats and more.

Best for food

Major food festivals each year allow travellers to sample the best of the city all in one place. Eat your way around the Chicago Food Truck Festival, or head to one of the Taste of Chicago events to sample extensive eats and live music from around the city. 

Best time-honoured eats

The Windy City is known for its deep-dish pizza, and Lou Malnati’s is one of the best. Later, try a classic Chicago hot dog (complete with mustard, pickle, tomato, relish, onions, and celery salt on a poppy-seed bun) at The Wieners Circle, where it is served with a side of Chicago attitude. And for a celebration, head to chef Rick Bayless’s Topolobampo for high-end Mexican food and top-notch cocktails.

The St Regis Chicago opened in May in a 101-storey tower steps from the city’s much-loved Riverwalk.

Best luxury hotel

The St Regis Chicago opened in May in a 101-storey tower steps from the city’s much-loved Riverwalk. Rooms are spacious and feature soaking tubs, natural wood, and the hotel’s signature butler service (at any hour, of course).

Best unique stay

Step back in time at the Chicago Athletic Association hotel, set inside an 1893 Venetian gothic building close to Millennium Park. Rooms feature original architectural details and classic black and white bathrooms. Don’t miss a drink at Cindy’s Rooftop for some of the best city views underneath a stunning glass atrium.

Get whisked up 103 floors to the top of the Willis Tower where visitors can step on to a fully glass balcony – aptly called The Ledge. Picture: iStock.

Best spot for a drink

Stepping into the Green Mill Cocktail Lounge is a bit like stepping back in time. The jazz bar, which once counted legendary gangster Al Capone as a regular and boasts tunnels beneath it, now features a full calendar of nightly entertainment. The bar is cash only.

Best spot to catch a foul ball

There’s nothing more classic than a day spent drinking an Old Style beer and cheering on the Cubs at Wrigley Field, but there are other spots to watch. Book a private party on Murphy’s Rooftop for excellent views of the field, or listen to the roar of the game with a cocktail in hand from the balcony of Alma at Hotel Zachary.

Best for budding architects

Sail along the Chicago River and marvel at dozens of buildings with an architecture river cruise with the Chicago Architecture Center. Or head south to the University of Chicago where ornate gothic buildings make you feel like you’ve stepped into Hogwarts.

The Obama Presidential Center will feature a museum, library, garden, and more. It is expected to open in 2025.

Best views

Get whisked up 103 floors to the top of the Willis Tower where visitors can step on to a fully glass balcony – aptly called The Ledge – extending more than a metre beyond the building walls. Look down at the lake and Chicago’s breathtaking skyscrapers, and learn about the city’s history in the process.

Feel presidential

Before becoming US president, Barack Obama lived on the South Side of Chicago. Now he’s building The Obama Presidential Center there, which will feature a museum, library, garden, and more. It is expected to open in 2025.

Hit the beaches

Chicago’s location along Lake Michigan means it boasts excellent sandy beaches and with amazing skyline views. The city has more than 41km of open lakefront. The beaches are free to access and swimming is permitted when lifeguards are on duty.

Originally published as Best things to do in Chicago