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25 October 2018
Chi-town’s got it going on. The Midwestern mecca is the third largest city in the US, and it’s pretty impressive, with a booming foodie and festival scene, amazing art and architecture, a crop of cool hotels, and a lake smack-bang in the middle of it all. Here’s where to eat, stay and play in Chicago – the city that inspired one of the most ~interesting~ baby names in history.
Time your trip wisely! The city’s glorious in spring and summer, and downright miserable in winter. There’s a reason they call it the Windy City.
Forget about counting calories – Chicago is the land of deep-dish pizza, beef sandwiches and hot dogs, and you’ll want to indulge in all of those iconic eats. And don’t worry about squeezing into your skinny jeans: the city balances it out with brunch and fab farm-to-table spots.
Skipped out on sightseeing? Tick the sights off your to-do list by grabbing a drink at Cindy’s or The Signature Lounge – both rooftop bars have panoramic views of the city.
There are two ways to go about this. Settle on an area, then choose a hotel that’s close to the hotspots, or stay at the hotel you’ve been stalking on Insta. Either way, these are our top picks:
Millennium Park. Get snap-happy at the city’s top tourist attraction. Millennium Park is home to The Bean – a silver steel sculpture that reflects the sky. If you visit Chicago and don’t take a selfie in front of it, the trip didn’t happen.
Skydeck. New York has The Rock, Paris has the Eiffel Tower… To get the sunset shot of Chicago, step out onto Skydeck, a glass ledge that juts out from the 103rd floor of the Willis Tower. This may be stating the obvious, but if you’re scared of heights, don’t do this!
Riverfront. Chicago’s lakefront is stunning, and the best way to explore it is by foot or bike. It’s lined with cafes, restaurants, bars and parks – make a pitstop at Olive Park for instaworthy views of the city skyline.
Wrigley Field. Catch a Cubs baseball game at this famous field. Before you head in, do as the locals do and get a beer at the Old Crow Smokehouse.
The Magnificent Mile. Splash some cash in the city’s biggest shopping district, which has a good mix of high street and haute shops. Then, wander along State Street.
Festivals. Chi-town has an insane festival scene. Music lovers, try to nab tix to Lollapalooza, the Chicago Blues Festival or the Chicago House Music Festival. Foodies, you’ll love Taste of Chicago and The Windy City Smokeout.
The Second City. This no-frills comedy club launched the careers of legends like Tina Fey, Joan Rivers, Stephen Colbert and Steve Carrell, so see a show for guaranteed LOLs.
Art Institute of Chicago. Whether you’re a culture vulture or someone who knows nothing about art, this museum is well-worth a visit. It houses some of the greatest, and most important art in history (like Andy Warhol’s). If art is your jam, you’ll like the Museum of Contemporary Art, too – it’s one of the biggest and oldest museums in the US.
Frank Lloyd Wright tour. Love architecture? You can take a guided tour of the famous architect’s home and studio, or go all out with a tour of Oak Park, the neighbourhood that has the most Wright buildings.
Words by Katia Iervasi.
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