Chicago: Where to eat, sleep, and play in Chi-Town

Chicago has long been known as New York's little sister. Set on the banks of Lake Michigan, the affectionately named 'Second City' is often unfairly overlooked on North American itineraries. 

I've previously travelled to The States on four separate occasions and never once considered Chicago, instead favouring west coast hotspots Los Angeles and San Francisco, and of course The Big Apple. 

But after four action-packed days in Chi-Town, I'll bully everybody I know into checking out this lush, modern city immediately.

Now, with Air New Zealand offering thrice-weekly non-stop flights from Auckland to Chicago – 15 hours there, 16 back – you have no excuse either. 

Whether you're an architecture nerd, a foodie, or just looking to bar hop and shop, Chicago is a city for grown-ups looking to let their hair down.

Fun (and free) sightseeing

There's a reason locals proudly tell you Chicago was the first city with the skyscraper.

You could easily spend your entire trip touring the world-class museums, getting to know some of the city's oldest buildings, and watching the world go by on the famous river walk.

Millennial Park is the Chicagoan version of the town square and home to its most-famous landmark, Cloud Gate, or simply, The Bean to locals.

Here you'll find free daily cultural events and an outdoor cinema in the summer. Plus, a public art collection sure to get any Instagrammer's excitement levels pumping.

Speaking of selfies, you've got to snap a shot at the historic Route 66 sign, which marks the start of America's most famous highway. And don't miss Buckingham Fountain – one of the largest fountains in the world – located in Grand Park. It operates from April to October and during winter is decorated with festive lights.

A day of sightseeing wouldn't be complete without a visit to the Chicago Cultural Centre. The historic building was once the public library before it was converted in 1977. It boasts grand marble arches and the world's largest Tiffany stained-glass dome.

Eat like a local

New York might think it's got the pizza game covered, but it doesn't have Chicago's deep-dish pizza, which can't be beat.

Deep-dish pizza is an institution here, just make sure you've got an empty stomach on arrival. The decadently dense treat is truly in a league of its own.

Unlike regular crusts, this one is crumbly, doughy and pie-like. Each pizza takes 30 minutes to bake and is brought to the table in its own pan. 

There's plenty of places to try the famous offering, but Gino's East is the go-to for locals and celebs alike, including Oprah and Jennifer Lopez.

The restaurant, located off Michigan Avenue, looks more like a graffiti museum – the work of customers scrawling their name on the walls while they wait for their food.

If pizza doesn't tickle your fancy (what's wrong with you?) another local favourite is Lou Mitchell's. Come for the old-school diner vibes and stay for the pancakes and mid-Western hospitality. Important: this haunt is not for the calorie conscious.

It's a Lou Mitchell tradition that female customers are given a small carton of Milk Duds upon arrival. Again, leave your diet at home.

A five-star stay

For a home base with warm, delightful service, a spa that will revitalise even the most jaded of humans, and a cloud-like bed, look no further than The Peninsula.

If you're familiar with the group – it has hotels in Paris, New York, and Tokyo –  you'll be aware of its signature old-worldly glamour and award-winning restaurants. The Peninsula Chicago offered all that, plus a choir of new friends in the form of the friendly staff.

In short, it's the kind of place you remember because of the way it made you feel, rather than the Insta-worthy décor. That being said, the champagne chandelier at breakfast made me feel things too.

Throughout winter, The Terrace is converted into an ice skating rink, surrounded by pine trees and fairy lights. Order your hot chocolate or hot cider, and settle in to your very own winter wonderland without even leaving the hotel.

With views overlooking Michigan Avenue, it's no surprise The Peninsula has won a bunch of awards including most recently being recognised as the best hotel in Chicago.

A different kind of ballgame

You don't have to be a baseball fan to visit Chicago's world-famous Wrigley Field.

From the beer, hot dogs, and patriotic supporters, to the ivy-coloured outfield walls, it's an experience like no other.

Don't miss the seventh-inning stretch –  a tradition that takes place in the middle of the seventh inning – where everybody gets up to stretch their legs and grab a drink before the alcohol vendors shut up shop.

But the best part? The song 'Take Me Out to the Ball Game' is played for crowds to sing along.

What're you waiting for? Make your next trip to Chicago – you won't regret it.