Insider: Dave Hilfman, Chicago

By Dave Hilfman

What should Kiwis know about Chicago before they visit?

Chicago is a city of distinct and ethnically diverse neighbourhoods that's easy to explore using the extensive public transportation system. Although downtown includes the most popular sightseeing, museums and other attractions, venturing beyond to other areas opens up the real culture of the United States' third largest city.

Are there any hidden gems in the city?

Water taxis shuttle commuters along the Chicago River and offer occupants stunning views of the city's skyline and architecture; for only a few dollars a ride, it's convenient and efficient.

Where should visitors base themselves?

The central areas of River North and the Loop are near major attractions and transit to travel throughout the city. Visitors can take the historic "L" train (short for "elevated") from the city's two airports directly to the Loop.

When is the best time to visit?

The Windy City comes alive in the summer, from May to September, with street and food truck festivals, art fairs, and concerts every weekend. Lake Shore Trail offers space for running and biking along Lake Michigan, and the beaches boast volleyball courts, water sports and beautiful views.

What are the top attractions?

As the second-tallest building in the United States, Willis Tower is Chicago's top attraction for good reason. The Skydeck, a glass observation deck stretching 1.2m outside of the tower's 103rd floor, provides incredible views, but is not for the faint of heart. Other popular outings include the Art Institute, home to Picasso's The Old Guitarist and Seurat's A Sunday on La Grande Jatte, or catching a baseball game.

What's the best comedy club?

The birthplace of improv, Chicago is considered one of the greatest incubators of comedic talent in the world. From local storefront theatres and clubs, to classic powerhouses like The Second City and iO Theater, the city offers opportunities aplenty to see live stand-up, improv and sketch comedy.

Any recommendations for somewhere to see live music?

As home to jazz and blues greats like Nat King Cole and Muddy Waters, Chicago offers a unique and rich history for live music. Today, local favourites like Buddy Guy's Legends and Kingston Mines are always buzzing late into the night, and you can still check out Al Capone's favourite booth at the legendary Green Mill Cocktail Lounge any night of the week.

What is the top spot for some deep-dish pizza?

Nothing beats Gino's East, the original. Flaky, gooey, and delicious. Lou Malnati's Pizza gives it a serious run for the money.

Are there any good craft breweries in town?

Chicagoans take a lot of pride in the local craft beer scene. Check out Revolution Brewing, Half Acre Beer Company, or Lagunitas for a tasty brew.

Where can you get a great coffee?

Grab a cup at local hot spots Big Shoulders Coffee, Ipsento Coffee House or Cafe Jumping Bean.

Where should we go to watch American sports?

Check out Ukrainian Village's The Anthem or Old Town Social.

If visitors can't get tickets to the All Blacks v Ireland game on November 5, where's a good place to watch it?

Fado Irish Pub and Paddy Long's are both great joints to meet up with fellow rugby enthusiasts, both Irish and Kiwi. You could also try out tried-and-true sports fan favourites like The Globe Pub or Black Rock Pub & Kitchen.

Why is Chicago a great travel destination?

Chicago has a little something for everyone. It's got nightlife, museums, team spirit, and Lake Michigan; the hustle of New York City with a Midwestern sensibility. The city itself is both historically and culturally rich, plus it serves more than 47 kinds of New Zealand beer. Cheers!

Based in Chicago, Dave Hilfman is United Airlines' Senior Vice-President, Worldwide Sales. United flies Auckland to Chicago via San Francisco. united.com

- Spy.co.nz

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