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Winging it: Chicago, IL revisited

No American city has upped its game in the last 20 years quite like Chicago. We go beyond deep dish and Yeezy.

What to do

Chicago’s skyline is world-famous for blending bold and contrasting architectural styles, from art deco and neoclassical to modern and commercial. The river has unobstructed views of a city that has influenced American architecture. Urban Kayaks offers two tours: the Chicago Riverwalk snakes through the city’s urban setting, or the Monroe Harbour tour will take you further out into Lake Michigan for a bit of tranquility.

Things can get pricey when you’re hopping between aquariums and art museums. The CityPASS eases the burden on your wallet and allows you to enjoy the city’s top attractions in VIP style. For $150, the pass grants access to major landmarks like the Field Museum, Skydeck and the Art Institute, and is valid for nine days after the first use. The best part? Skipping the ticket line every time.

Chicago’s Millenium Park is a year-round hub for tourists but really comes to life in the summer. Adventure seekers should head to the climbing walls, a dramatic outdoor structure that is one of the largest of its kind in the world. Different styles of rock climbing are available to suit individual experience. The 40-foot peaks have great views of Grant Park.

What to eat and drink

Consider Revival Food Hall one-stop shopping for your stomach. Revival is part of the current wave of downtown food halls. Evolving from dawn to dusk, the hall features some of the city’s best pop-ups, rotating throughout the seasons. All 15 fast casual establishments have roots in Chicago, with a menu that presents an impressive array of options, spanning Americana to Tex-Mex. Stop in for Chicago-style deep dish pizza, third-wave coffee and tacos.

As one of the city’s flourishing food neighbourhoods, Logan Square has many small bars and restaurants that present a refreshing, intimate feel. Giant wins for its unpretentious vibe and Midwestern menu, accented by international notes. Start with biscuits served with jalapeno butter but save room for king crab tagliatelle. If you want a show with dinner, ask to sit at the chef’s rail. It's noticeably livelier than the rest of the space.

There’s no shortage of bar-meets-gaming experiences in Chicago. Our pick is the British import that pairs darts with bespoke cocktails and bar snacks. Flight Club takes the kinetic experience of throwing darts and combines it with automatic scoring tech for an addictive experience. The social phenomenon is suited for all group sizes, too; face off with friends or network across the entire room for a super-charged battle. Skip the beer, the bar’s classic cocktails are more suited to missile tossing.

Where to stay

A short walk from the Magnificent Mile, the luxurious Gwen Hotel pays homage to the glamour of 1930s Chicago. Art deco design is prevalent from the lobby to the spacious suites and the hotel bar. The bar is a great place to get acquainted with Chicago’s celebrated cocktail culture. In the summer, the hotel has a “glamping” suite with outdoor accommodations on a private terrace.

One of Chicago’s newest hotels, the art deco-style Kimpton Gray is a slightly upmarket stay in the Loop with easy access to entertainment and shopping on Michigan Avenue. A lively rooftop lounge, Boleo, offers panoramic views of downtown Chicago. Kick off the evening with the cocktail bar’s silver-cart champagne service.

Chicago’s waterfront is often overlooked in lieu of skyscrapers and art exhibitions. The W Hotel offers affordable luxury in a boutique-like setting, and draws a younger crowd to the area across from Ohio Street Beach. All rooms are equipped with W’s signature plush bedding. At night, the lounge livens up with guest DJs and dancing.