Don't miss these must-sees on a visit to Chicago, writes Stephanie Holmes.

Although I love the old favourites like New York, San Francisco and LA, Chicago is way up there as one of America's greatest cities. It's been in the news of late due to scary lift falls and hospital shootings, but don't let that deter you from a visit. It's a fabulous destination for Kiwis and is about to get a lot easier to reach, with Air New Zealand launching their direct route from Auckland to Chicago this week.

Although it's a whopping 15-hour flight, the new route is worth it — further opening up the US to Kiwis, giving easier access to the Midwest and east coast, as well as giving another option for a stopover city on the way to the UK. Flying from Chicago to London takes only 7.5 hours. Better still, you can fly direct to Reykjavik, Iceland — one of the world's top trending tourist destinations — in a little more than six hours with Icelandair.
But Chicago in its own right has a lot to offer, from great architecture to world-famous art and music; fine dining to classic comfort food; stadium sports to shopping.
Here are some of the highlights worth checking out when you're there.


Art Institute of Chicago


One of the most famous paintings in US history, Grant Wood's 1930 work American Gothic hangs proudly in Gallery 263 of the

Art Institute of Chicago

. Also featured in the museum's impressive

American Art collection

is Edward Hopper's Nighthawks (1942), and Archibald John Motley jnr's Nightlife (1943), and there are countless other works to wow you in this building that takes up the best part of a whole city block. If you're short on time, the institute's website gives a guide on how to see the best works in under an hour — taking in Monet, Warhol, Chagall and more.

AIC is part of the city's Grant Park, 130ha of public land in the CBD, where you'll also find Millennium Park (home to Anish Kapoor's Cloud Gate, better known as The Bean), the Buckingham Fountain and the Museum Campus, which is home to the Field Museum of Natural History, the Shedd Aquarium and the Adler Planetarium.

The Art Institute of Chicago. Photo / Getty Images
The Art Institute of Chicago. Photo / Getty Images




Museum of Contemporary Art

is one of the world's largest, dedicated to works of art spanning 1945 to present day. Founded in 1967, it now boasts more than 2500 works in its permanent collection, with a focus on the provocative side of contemporary art and culture. Artists include Ansel Adams, Francis Bacon, Jean Michel Basquiat and Jeff Koons. There are frequent special exhibitions, and free tours offered daily.

Kingston Mines
Chicago is famous for its music scene — historically the city was key in the development of jazz, blues, rock 'n' roll, hip-hop and dance music — and you'll never run short of options to see live performances, no matter what time of year you visit. There are the big festivals, like the Chicago Blues Festival in June, or the Jazz Festival and Lollapalooza in August, but there's nothing better than heading to an intimate club for a fun night out. Buddy Guy's Legends is one of the most famous, thanks to its namesake founder who, at 82, still takes to the stage to perform. But you'll also find a great night at Kingston Mines, the largest and oldest continually operating blues club in Chicago. It has live music every night, and if you follow the club's motto you can't help but have a good time: "Hear blues. Drink booze. Talk loud. You're among friends!"


Chicago's First Lady Architecture River Cruise

The Great Fire of 1871 destroyed about 9sq km of the city, leaving 100,000 residents — around a third of the population — homeless. More than two-thirds of the city's structures were made of wood and most were destroyed. But the city rose from the ashes with a construction boom rebuilding bigger and better, leading to the construction of the world's very first skyscraper, the Home Insurance Building, in 1884. Now, the Chicago River is lined with multi-storey scrapers, giving the city a Gotham-like, film-noir feel, best experienced from the water.

Chicago's First Lady Architecture River Cruise

is a small ship cruise manned by passionate volunteers in partnership with the Chicago Architecture Centre. The 90-minute tours run from April to November, with between four to eight departures each day.

Greeter Tours
If you prefer walking to cruising, Chicago Greeter is a free service where a volunteer will take you on a guided tour of a specific part of the city. Visits can be customised based on your interests and what you'd like to see — sign up on the website at least 10 days in advance and you'll be matched with a greeter who best meets your needs. Or, if you'd rather do things more spur of the moment, hour-long InstaGreeter tours are offered on a scheduled basis — head to one of the designated meeting points and find the waiting volunteer who will take you around. Tours are completely free, and there is a strict no-tipping policy.

Magnificent Mile
To see some of the city's best architecture on your own schedule, take a stroll down the Magnificent Mile and you'll pass some Chicago icons, like the Tribune Tower, The Wrigley Building, the London Guarantee Building and 333 N. Michigan Avenue. It's also where the best shopping can be found. There are more than 460 retailers in this area, including big department stores such as Bloomingdale's, Macy's, Saks Fifth Avenue and Nordstrom, plus small boutiques, designer labels and family-favourites like the Disney Store and American Girl.

The Ledge at Sky Deck

The Ledge at Skydeck, in Chicago's Willis Tower. Photo / Supplied
The Ledge at Skydeck, in Chicago's Willis Tower. Photo / Supplied

The best way to see the city is from above, but if you don't have access to a private plane or penthouse apartment, the next best thing is to head up to the 103rd floor of the Willis Tower to the Skydeck and its award-winning attraction, The Ledge. This fully enclosed glass balcony extends 1.2m outside the tower giving you a bird's eye view of the streets below. On a clear day you can see across Lake Michigan and potentially out to Illinois' four neighbouring states. The Ledge is open year-round (although extreme weather conditions might temporarily close things) and it's a great experience, making for some Insta-worthy photos.


No trip to the States is complete without a visit to a sports game. Americans just do live sports much better than we do. There's a spectacle element to the whole proceedings so even if you're not a sports fan, you're still guaranteed fun.

I visited Soldier Field for an American Football game between the Chicago Bears and the Green Bay Packers — a huge match that had the stands crammed, even in freezing rain and minus-2C temperatures. In the many breaks, there were cheerleaders and dancers and live bands, as well as cheap beer and hotdogs. Chicago also has Major League baseball (Cubs and White Sox), basketball (Bulls and Sky), ice hockey (Blackhawks), and soccer (Fire and Red Stars). The best way to secure tickets is through US Sports Tickets, an online specialist that allows you to find seats to all the major games and pay in your local currency.


Hot dogs and pizza

You can't go to Chicago without experiencing two of its most famous foodstuffs — deep-dish pizza and the all-important hot dog. Talk to any Chicagoan and they'll have a favourite joint to recommend, but for pizza you can't go past Lou Malnati's, Gino's East and Giordano's. For hot dogs, head to Superdawg, Gene & Jude's and Murphy's Red Hots.

If you're thick-skinned, head to Wiener Circle in Lincoln Park, where the staff have become notorious for throwing out insults at customers. It's not meant to offend — it's all part of the schtick here, and customers are encouraged to give as good as they get.

If you love Italian food, don't miss a visit to Eataly — a marketplace and foodhall, consisting of restaurants, food counters, bakery, retail and cooking school. It's a great option for a quick lunch — grab a reasonably priced sandwich on freshly baked bread with simple fillings like tomato, mozzarella and basil. Then try your best to resist filling up your suitcase from the aisles.

Cafe Spiaggia
For more Italian fare, in a casual restaurant setting, head to Cafe Spiaggia on the Magnificent Mile for shared plates, handmade pastas and an exceptional wine list selected by award-winning sommelier Rachael Lowe. This is the sister restaurant to Spiaggia, a high-end fine-dining option next door. In Cafe Spiaggia, they won't mind if you arrive in your jeans and trainers after a day traipsing the streets.

Publican Anker
In an industrial-chic building in the trendy Wicker Park neighbourhood, Publican Anker is a beer-hall style restaurant with an interesting, seasonal menu heavy on vegetables (a honeycrisp apple salad with brussels sprouts, smoked cheddar and walnuts is divine), as well as burgers and charcoal-grilled fish and meats. You don't have to come in for a full, sit-down meal — grab a stool at the bar for a drink, some snacks and great people-watching out to Wicker Park.

The Violet Hour
Speakeasy bars are all the rage and they're great . . . providing you can find them. The Violet Hour in Wicker Park is so well hidden we passed it a number of times before we realised the bare purple lightbulb above a mural was actually indicating the doorway. Inside, we walked through a dark hallway and through heavy velvet curtains to get to a dimly lit bar for a cocktail-making class. Under the tutelage of barman Abe, we learned how to properly make Old Fashioneds and whiskey sours . . . then drank them to test our talents. The bar is also open to regular guests, although the house rules are pretty strict: "No cellphone use inside lounge. Proper attire requested. No baseball hats. No Jager-Bombs. No Budweiser. No Light Beer. No Grey Goose. No Cosmopolitans. And finally, please do not bring anyone to the Violet Hour that you wouldn't bring to your mother's house for Sunday dinner."

Air New Zealand launches direct flights from Auckland to Chicago next Friday, continuing three times a week on Wednesdays, Fridays and Sundays. One-way Economy Class fares from $1019.

The Omni Chicago is in the Magnificent Mile district and offers all-suite accommodation, from $633 per night on Expedia.
Purchase a City Pass and get discounted access to more than 25 attractions.