A First-Timer’s Guide to Sensational Chicago

08 Jun 2017

I’ll be honest with you, I didn’t expect much from Chicago. When you’ve been to the USA’s big hitters like New York, San Francisco and Los Angeles, surely you’ve seen the best of American city living? This assumption was proven very wrong very quickly, from the moment I arrived in Chicago. As soon as I saw the skyscrapers, met the warm, welcoming people and began pounding the pavement, I couldn’t wait to see as much of it as I could in the 48 hours at my disposal. So if you’re a first-timer like I was, be sure to follow this guide of things to do in The Windy City:

The Chicago skyline (image: Alexandra Gregg)

Ride a Big Bus

Those who are adverse to sitting or being semi-sedentary on a city break may scoff at the thought of spending time on a tour bus, but there’s no doubt that Chicago’s Big Bus Tours are a great way to get your bearings as soon as your arrive. Hop-on and hop-off at all the city’s biggest sights – including family-friendly stops like the Field Museum or the Adler Planetarium – and, when the weather takes a turn, you can stay dry and warm (with free Wi-Fi) onboard.

Reflections in The Bean (image: Alexandra Gregg)

Reflect at The Bean

Cloud Gate, or as you’ll probably know it ‘The Bean’, is easily Chicago’s most iconic structure – despite being just 11 years old. Its wacky, funhouse-mirror style makes it one of the most unique sculptures in the States. Inspired by the properties of liquid mercury, the aim of Brit-based Anish Kapoor in The Bean’s creation was to engage the Chicago skyline and the verdant surrounds of Millennium Park… something it does with gusto. It’s great at engaging the public too; it’s one of the most photographed spots in the city, not to mention one of the best places to grab a selfie.

Me (middle) doing TILT! (image: Sarah Barnett)

Do TILT! and The Ledge

With the Willis (Sears) Tower and the John Hancock Building both competing for the best Chicago views, it can be tricky to know which one to do. Our advice? Try both. The Ledge at the Willis Tower extends 1.3 metres from the skyscraper’s 103rd floor, making it great for quirky poses (like handstands, cheerleader pyramids etc.). TILT! at 360 Chicago, on the 94th floor of the John Hancock Building, offers a great way to get your adrenaline rush while seeing the city. The glass ledge tips out 30 degrees, so you’re forced to gaze down at the pavement, 310m below.

Deep-dish pizza at Pizano's (image: Alexandra Gregg)

Eat deep-dish pizza at Pizano’s

You can’t go to Chicago and not try a slice of deep dish, aka pizza pie. I’d been forewarned that, even as a pizza lover, I may not enjoy this particular style. “It’s too much like a pie, too thick,” one member of my group said. “It’s not pizza! You won’t like it,” she added. But I was determined to give it the benefit of the doubt.

Sitting down at the family-friendly Pizano’s Pizza and Pasta in East Madison Street, we promptly ordered three styles of deep dish: Meat Lovers, Vegetarian Special and the Rudy’s Special. I dove straight in for the meatiest of the bunch and discovered that my travelling companion was right… it wasn’t pizza. Instead it was a delicious pizza-pie hybrid that was packed full of flavour and crunch, and I loved every morsel. Take heed though: a couple of slices will easily fill you up, so if there are just two of you, order a small (10”).

Be sure to try the pancakes at the Pittsfield Café (image: Alexandra Gregg)

But remember there’s other food too…

Beyond legendary Italian beefs, pizza and hot dogs, Chicago’s culinary offering serves up so much more. In fact it boasts 32 Michelin stars, with Conde Nast even claiming that the city has the best restaurant scene in America. Simply put, it’s a foodie paradise, so dare to stuff your face as much as you can.

An Andy Warhol classic at the Art Institute of Chicago (image: Alexandra Gregg)

Visit the Art Institute

Generally speaking, I’m not a fan of museums and galleries. I have a relatively short attention span and I also love being outdoors, so the thought of being stuck inside, reading informative plaque after plaque (after plaque) fills me with dread. But the Art Institute of Chicago is unlike any other gallery I’ve been to. First off, it boasts some of the most famous paintings in the world – ones like American Gothic that even I, a self-proclaimed art novice, could name. It’s modern, airy and unstuffy, and showcases quirky collections like the fascinating Thorne Miniature Rooms, which portray 68 scale models of European and American rooms from the late 13th century to the 1930s. You can easily while away a couple of hours in here, and feel smugly cultured after.

Segwaying at Lake Michigan with Absolutely Chicago Segway (image: Sarah Barnett)

See the city from Lake Michigan

Full of innovation and experimentation, Chicago’s architecture is what makes it one of the most unique cities in the States. And this unusual skyline is best experienced from the water – you can take a boat tour to cruise the lake and river and gaze up at the high-rises, or you can whizz along the banks on a Segway, discovering the waterfront at breakneck speed (well, 10mph). Whichever you choose, you’ll quickly realise the beauty of the city’s design, not to mention the sheer size of Lake Michigan – the second largest of the Great Lakes of North America. It’s so big, that the city feels like it’s set on the coast, rather than inland.

Centennial Wheel at Navy Pier (image: Alexandra Gregg)

Stroll Navy Pier

The name ‘Navy Pier’ just doesn’t do this 101-year-old Chicago landmark justice. Jutting out into the lake, it boasts a theatre, Ferris or ‘Centennial’ wheel, a grand ballroom, a funhouse maze and a plethora of restaurants – not to mention a whole host of new attractions under construction. With the sun shining and the water blissfully calm, it’s the perfect place to enjoy a fun day out with the family.

The Palmer House Hotel also has some great signature drinks and dishes, like this orange cream soda (image: Alexandra Gregg)

Stay in a historic hotel

Chicago may not be England-level historic, but it does have a rich past that’s worth exploring. The Palmer House Hotel, where I stayed, is a prime example of that. This timeless property is a member of the Historic Hotels of America, lauded for its namesake, Potter Palmer. Despite the hotel falling victim to the Great Chicago Fire less than two weeks after it opened in 1871, Potter successfully negotiated a US$1.7m loan to rebuild the hotel, and was able to reopen its doors to guests just two years later. His determination is an inspiration to the city, and the quick reconstruction of the hotel meant it was one of the first major buildings to be erected after the fire.

Shop the Magnificent Mile (or at the outlets)

If you’ve got any dollars left at the end of your trip, splurge in the shops. There is a plethora of high-end stores and boutiques along the famous Magnificent Mile or, on your way back to the airport, stop off at the Fashion Outlets of Chicago and bag yourself a bargain. I managed to get a dress, a necklace, six pairs of earrings and a one pound bag of pick ‘n’ mix for less than US$50. It was an absolute steal.


Discover the Windy City and the Deep South on our Chicago to New Orleans Journey – make an appointment with a Travel Expert to find out more about this tailor-made holiday itinerary.


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Alexandra Gregg

Once a roving local news reporter and now a travel-obsessed writer/sub, I'm head-over-heels for nature, wildlife and the ocean. When I'm not getting up close to animals and sea creatures, I'm seeking out the sets of my favourite TV shows around the world. Follow me @wonderg1rl89.