Exploring The Windy City: The Best Of Chicago, Part Two

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Chicago is a world class destination, straddling the shores of Lake Michigan and nicknamed the “Windy City”. Along with a vibrant arts scene, cultural attractions, top notch shopping, great restaurants, and fascinating architecture, the city also has plenty of five star and boutique hotels. For first timers visiting Chicago there are plenty of surprises to enjoy, including experiences unique to the city, and getting there from Australia will be easier thanks to new direct Qantas flights operating four times a week from Brisbane starting in September 2020. So if you’re planning to take advantage of the new route - which is the longest in the world - what can you expect? Here’s part two of our special two-part feature on Chicago, focussing on eating, drinking where to stay and more.

Attend A Major Sporting Event

Chicago is many things including a city where sport is taken seriously. Just a few of its key teams include the Chicago Bears in American football, the Chicago White Sox and Chicago Cubs in baseball, and the Chicago Bulls in basketball. While obtaining tickets for American football and basketball can be tricky, there are usually more options when it comes to baseball. The finest ballpark in the city is Wrigley Field, home to the Chicago Cubs, which was built in 1914 and it is the second-oldest Major League Baseball park in the US, second only to Fenway Park in Boston. This famous sporting arena has seen some legendary moments in baseball history, including the 1917 no-hitter pitching duel between the Cubs' Jim Vaughn and the Reds' Fred Toney, and Babe Ruth's "called shot" during game three of the 1932 World Series. Ballpark tours are conducted in-season if you are curious, but it’s much more fun to visit on game day instead and catch a game with the locals.

Go Shopping 

The exchange rate may not be as favourable as it used to be at the time of writing, but the USA, and Chicago in particular, offer Australian shoppers a lineup of great stores and great products to bring home. Top of the list, especially if you don’t have much time, is the Magnificent Mile or Mag Mile, located on Michigan avenue between the Michigan Avenue bridge and the Oak street. It offers a lineup of department stores such as Saks Fifth Avenue, shopping malls such as The Shops At North Bridge, and a lineup of big brand high end boutiques. The famous Oak Street is a great place to combine shopping and cocktails as well as offering a more tranquil shopping experience. Dubbed the Magic Mile, it’s located close to Michigan Avenue at the Gold Coast, and the place to browse among a wide-range of designer boutique stores from Giorgio Armani to Prada. The shops of Lincoln Park are also worth checking out, particularly if you are into upcoming designers, and for fashionistas Bucktown and Wicker Park has most of the big names of the fashion arena, as well as being a cool, artsy neighbourhood. And finally, for bargain hunters, just an hour away from the city is Gurnee Mills, which has a combination of discount stores and full price outlets.

Unique to Chicago

If you visit Chicago in the winter months, put ice skating on The Ribbon on your list of things to do. Located in the Maggie Daley Park in the heart of downtown Chicago, and with the City’s skyline as a backdrop, The Ribbon is an outdoor ice track which meanders through a rolling landscape to provide an ice skating experience like no other. Entry is free and skates are available to rent with the ribbon usually open until late March. The Chicago Polar Plunge is another - if only as a spectator! Held at the beginning of March at North Avenue Beach in Lincoln Park, it’s a special event to raise money for the Special Olympics where thousands of people brave freezing temperatures to charge into Lake Michigan’s icy waters. Also unique to Chicago is the Garfield Park Conservatory. A favourite place for locals, it’s one of the largest of its kind in the country, filled with plants, flowers, and trees and haven from the hustle and bustle of the city. It’s also a great place to take a break from the cold during the winter months, and entry is absolutely free! Chicago is also a wonderful place to see a Broadway-like show, with world class venues including the Steppenwolf Theater and the Goodman Theatre.

Take A Tour

Chicago's history is a big part of what makes it so unique, and taking a tour is a great way to learn about the city's past, from the famous buildings to notorious gangsters. Chicago's Landmarks is a half-day narrated coach tour taking in all of the city's most important landmark buildings and sights, including a scenic drive along the lake through Grant Park, down Chicago’s Magnificent Mile, and exploring the South Side including President Obama's former home. If you prefer to go at your own pace, the Hop-On-Hop-Off Bus or Trolley Tour is your best bet, as well as the easiest and most convenient way to see the highlights of the city. If you are visiting during the warmer months, a Segway Tour is another option, operated with small groups of just eight people and one guide. Another interesting option is the The Chicago Mob and Crime Tour, which visits sites associated with some of the city's most notorious gangsters of the 20th century including Al Capone. And during the summer months, the Chicago Architecture River Cruise is a 75-minute tour sailing past the city's fine buildings. 

Stay Somewhere Fabulous

For most visitors, organising a hotel in the city center is recommended so you’ll have access to the best sightseeing, shopping, dining and sights including architecture. The city center encompasses the famous Magnificent Mile and areas of the waterfront, which are particularly popular in summer. And for first timers there’s plenty of choice, from brand new hotels, to classics which have undergone dramatic renovations. At the luxury end of the scale are hotels including The Langham, which has a lovely riverfront location as well as being close to the Magnificent Mile, Millennium Park, and Navy Pier. The Hyatt Chicago Magnificent Mile has also had a recent renovation, while the Radisson Blu Aqua Hotel has beautiful views over Lake Michigan and Millennium Park. For something a bit more stylish and unusual, the Acme Hotel Company is a hipster hotel located in Chicago’s River North neighbourhood with a focus on tech including free Wi-Fi, keyless room entry via an app, Amazon Echos in every guest room and ESP Guitars in every suite. Also one to consider is Virgin Hotels; located in a stately old bank building, it has a cherry red colour scheme, while being clubby and retreat-like at the same time. And the contemporary-chic Viceroy is a designers delight, with a retro Chicago façade and mid-century furnishings, with a highlight being quotes from Marcel Proust reproduced on the lobby wall.

Chicago’s Cuisine

Chicago used to have a bit of a reputation as a meat and potatoes kind of town, but that’s no longer true. Restaurants in the Windy City today have a level of sophistication that rival any food scene in the USA; although you can still get great steaks and hot dogs, as well as deep dish pizza, the city has Michelin-starred dining experiences, and some amazing cocktail bars. There are hundreds to choose from, and all types of cuisine on offer, but just a few to put on your list include Gibsons Bar & Steakhouse, located on North Rush Street. A Chicago icon since it opened its doors in 1989, its famous for prime Angus beef, fresh fish and classic cocktails. Also the curiously named Girl and the Goat, located on West Randolph Street, is a decade-old hot spot where chef Stephanie Izard serves up innovative small plates from a dramatic open kitchen. Located in Chicago’s historic Fulton Market District, Aba is a Mediterranean restaurant with a lovely rooftop patio, offering a lighter style of cooking with influences from the Mediterranean, including Israel, Lebanon, Turkey, and Greece. Meanwhile Galit is Middle Eastern venue in Lincoln Park, with a menu focussing on a seasonal approach to dishes of the Middle East and Israel’s immigrant cuisines. And finally, Chicago is the home of pizza with a visit to Coda Di Volpe, located in the Lakeview area, essential especially for fans of classic southern Italian cuisine including pasta, pizza, steak, and seafood.

A Pick Of Chicago’s Best Watering Holes

Along with restaurants, hotels, sights…..well, pretty much everything, Chicago has more than its fair share of amazing places to have a cold beer or a cocktail. A top pick is the roof top bar at the Peninsula Hotel, Z Bar, which is arguably one of the best in the city. Located on the sixth floor, the bar opened in 2018 with a different perspective of the Mag Mile, fancy cocktail carts, and decadent drinks with ingredients like 24-karat edible gold flakes. Meanwhile Vol.39, at the Kimpton Gray Hotel, is inspired by 1940s lounges, with book-lined walls and tufted-leather sofas. Also at the hotel is Boleo, located on the roof, with a Peruvian vibe and old-fashioneds as a focus. Ada Street is Chicago's go-to spot for a romantic night out, and located just northwest of Goose Island. Here the cocktails are inventive, with a rotating menu. Celeste is a River North venue reminiscent of an English garden, and boasting a retractable roof which makes for year-round seasonal cocktails. And finally, Cindy’s offers cocktails along with some of Chicago's most spectacular views across Millennium Park, the Art Institute and Lake Michigan.




Jacqui Roth


  • 4
    Love The Shopping

    Posted by Alyce on 9th Mar 2020

    Hate the x-rate though. It used to be so good, but the Aussie dollar is rubbish now.

  • 4
    Love Sports

    Posted by Jackson PIke on 9th Mar 2020

    A friend got us Laker tix when we went on holiday to LA a few years ago. I wasn't a basketball fan but wow, I am now!

  • 4

    Posted by Tim 9 on 9th Mar 2020

    Great ideas here. Reckon the flight would kill you though LOL