Things to do in Chicago

Must-see Chicago sights

With its bewitching ensemble of skyscrapers that rise up from Lake Michigan, Chicago is one of the great American cities.

  1. See Chicago’s architectural wonders
  2. Drop into The Art Institute of Chicago
  3. Explore Chicago’s holy trinity: pizza, hot dogs and Italian beef
  4. Take in the view from the Willis Tower
  5. Lounge around Lincoln Park
  6. Visit Hemingway’s Birthplace and Museum
  7. Rock out to live music

As well as a selection of world-class museums, Chicago has a long list of icons and legacies, forever linked with the gangsters of Al Capone, the blues of Muddy Waters and the gravity-defying dunks of Michael Jordan. Although perhaps it’s those lip-smacking deep-dish pizzas that are the biggest legends of all.

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1. See Chicago’s architectural wonders

Chicago is jam-packed with iconic architecture that will keep you looking up. Art Deco skyscrapers and landmark Frank Lloyd Wright treasures are hard to miss. But if you want to know your tall-building trivia – such as which featured in a Batman movie – one of the city’s 85 guided tours should be on your list of things to do in Chicago. The Chicago Architecture Foundation’s tours are ever-popular, especially the twilight river cruise. If you’ve been walking around all day, a ride on one of these luxury boats with a cocktail in-hand is simply the best way to see the sights.

Tip: A Foundation river cruise ticket (around $50) gets you a $5 discount off the Chicago Architecture Center, normally $12.

2. Drop into The Art Institute of Chicago

The Art Institute of Chicago ranks as one of the greatest art museums in the world. Guarded by an iconic pair of bronze lions, it houses more than 300,000 artworks, displayed in a sprawling complex of galleries and halls. Even the least arty person will recognise some of the big-hitters in here: Edward Hopper’s Nighthawks and Grant Wood's American Gothic among the modern American work, with European impressionists such as Van Gogh, Gauguin and Matisse in there too.

Tip: The Thorne Miniature Room is like Alice in Wonderland. Recreations of architecture and furniture are on a 1:12 scale.

3. Explore Chicago’s holy trinity: pizza, hot dogs and Italian beef

Let’s be honest, one of the best things to do in Chicago is feast on a deep-dish, cheese-laden pizza. If you only pig out once, make it at Labriola, an Italian restaurant waited by slick-haired locals who look straight out of Goodfellas. You shouldn’t miss trying a Chicago-style hot dog at local drive-in Superdawg, or an authentic Italian beef sandwich (thin cuts of seasoned roast beef covered in jus served on a French roll) at the standing-room-only original Al’s Beef, on Taylor Street in Little Italy.

Tip: The US Pizza Museum shows how Italian immigrants introduced pizzas to America.

4. Take in the view from the Willis Tower

Empire State who? The 1451ft Willis Tower (formerly the Sears Tower) is the tallest building in the Western hemisphere. It’s so huge that it has more than 100 elevators – these ascend, in little more than a minute, from the ground-level shopping mall to the 103rd-floor Skydeck Observatory for mind-bending views. On a clear day, you can see four different states.

Tip: For really wobbly legs, step onto one of the glass boxes that protrude 4.3ft from the Skydeck, 1,353ft in the air.

5. Lounge around Lincoln Park

This is Chicago’s biggest green space. In summer, Lincoln Park provides a much-needed respite from the gridded pavements of the rest of the city. It’s packed with leafy nooks and crannies, monuments and sculptures, and has a couple of friendly, family-oriented beaches at the eastern ends of North and Fullerton avenues. Great if you’re aiming for cheap holidays to Chicago. The small Lincoln Park Zoo at the heart of the park is renowned for its menagerie of African apes and curious red pandas. Nearby you can rent paddleboats or bikes. If the weather’s bad, head for the pleasantly humid Lincoln Park Conservatory, a giant greenhouse built in the 1890s, or the Peggy Notebaert Nature Museum, with family-friendly exhibits on the local environment and wildlife.

Tip: After your day in the park, the place to wind up is North Lincoln Avenue for its cool cocktail lounges, dive bars and comedy clubs.

6. Visit Hemingway’s Birthplace and Museum

Did you know author Ernest Hemingway was a Chicago boy? He was born in the Oak Park neighbourhood in 1899, in a Queen Anne-style townhouse that’s been beautifully preserved and is accessible via tours that run throughout the day. Two blocks south is the Hemingway Museum, which chronicles his life with such exhibits as his childhood diary, a copy of the “Dear John” letter (in which he was dumped by Agnes von Kurowsky) and several absorbing videos.

Tip: Mega-fans, keep an eye on the events at hemingwaybirthplace.com website to see if there’s a guest speaker during your trip.

7. Rock out to live music

Live music has got to go on your list when you’re choosing what to do in Chicago. This city really swings, from its old-school blues beats to the local indie rock and hip-hop scene. Start at the House of Blues, which brings the spirit of the Mississippi Delta to the city, or sip cocktails beside the stage at The Bassment (get it?), a subterranean speakeasy known for its live bands. For more riotous punk acts paired with beer and a rooftop patio, try Reggie’s Rock Club located just south of downtown. If you’re feeling particularly adventurous, you can even get a little bit country at the recently reopened late-night honky tonk-style favourite Carol’s Pub.

Tip: In June, join in at the free Chicago Blues Festival in Millennium Park.

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