Steely skyscrapers. Ocean-like Lake Michigan and city beaches. Deep dish pizza. The electric blue of Chicago River. A gritty history of greedy politicians and powerful gangsters, which earned Chicago the nickname “The Windy City”, in reference to the “windbag” city leaders. The USA’s third-largest city has captured my imagination for a long time, so I was very excited to visit for a few days in September.

I had high expectations for Chicago, and in fact I was secretly a little worried that I’d like it so much, that I’d wish David had been transferred to the Chicago office rather than New York. I expected a vibrant, cultural city but on a more manageable and affordable scale, with a slightly slower pace. Essentially, I imagined it to be a smaller and more liveable New York.

But I was using my Australian brain. Adelaide is like a much-smaller Melbourne, or so I hear. Brisbane often feels like a smaller Sydney. I didn’t account for the regional diversity in the USA – moving between the regions of the USA can feel like moving between different countries.

When I arrived on a Tuesday afternoon, I was surprised to find nearly-deserted streets in downtown Chicago. Wide roads, larger stores and restaurants and generic American signage and shop fronts. I was surprised how strikingly different Chicago was to New York, even in the first five minutes.

Like a smaller New York? Not at all. Lots to love? Absolutely!

The capital of the Midwest

Chicago is the largest city in the Midwest, America’s heartland. The region is made up of states like Indiana, Michigan, Ohio, Minnesota and the Dakotas (and obviously, Illinois), and conjures up images of wide open spaces, cornfields and prairies, the Great Lakes and industrial manufacturing cities. The Midwest is considered the barometer of what Mainstream America is thinking, doing or feeling. The “General American” accent of the Midwest is the accent adopted by news anchors and the rest of the broadcast media. I was startled to hear that the people around me in Chicago all sounded like Americans on TV, compared to the distinctive New York accent that I’d grown used to.

Midwesterners are often described as hard-working, friendly and down-to-earth. Life is a little slower and more affordable. True to the stereotype, Midwesterners were generally very friendly and welcoming.

Millenium Park & Cloudgate

I started at Millenium Park, at the famous reflective sculpture, Cloudgate, AKA The Bean. It looks like a giant silver jellybean, and all the photos I’d seen of selfies taken with selfie sticks amongst huge crowds didn’t really sell it to me. I swung past anyway, to see what all the fuss was about in person.

I was totally enchanted by the changing reflections of the city and surrounding park on the sculpture’s surface. It’s one of the most engaging pieces of public art I’ve ever seen, and I spent a long time playing around with the reflections of the city that could be found from different angles. It helped that at 7:30am, there weren’t many other people around, so I could focus on the reflections of the landscape rather than of the crowds.

Architecture in Chicago

One of Chicago’s greatest assets is it’s bold and striking architecture. While there are a handful of notable buildings dotted all over the city, the greatest concentration of these is in a small section of downtown Chicago, by the Chicago River.

The glorious and ornate Wrigley Building, opposite the moody magnificence of the neo-gothic Tribune Tower makes for one of the most striking spots in Chicago. From this point, I took the stairs down to the riverbanks and walked The Chicago Riverwalk, which was easily one of the highlights of my trip. Parts of the walkway along the river jut out, allowing for the best photo opps back along the river. I went early in the morning, around 8:30am, and had the place largely to myself.

See more: In Photos: The Chicago Riverwalk

At Millenium Park, I also briefly admired the Frank Gehry-designed Jay Pritzker Music Pavilion, and afterwards I only had to cross the road to find the famed Tiffany Dome, inside Chicago Cultural Center. The dome is a 38-foot domed glass ceiling, installed by famed Louis Comfort Tiffany in 1897, when the building was the city’s public library. The whole building is gorgeous, and on my way to find the dome I got lost, and took a scenic route which led me to lots of other pretty features. When I visited, there was a classical pianist playing in the hall, as part of a free cultural program.

Natural Beauty

I’d seen photos of the bright blue Chicago River, and totally assumed it was a Photoshop trick by tourism boards and operators. I could barely believe my eyes when I saw that the river really is that shade of vibrant aqua, running like an electric blue jolt through the skyscraper-jammed downtown district. I wish the Brisbane River was this blue (rather than it’s murky brown at worst, and brown-green at best).

Chicago also sits on the edge of Lake Michigan, one of five Great Lakes. The city has beaches, and from the edge of the water, Lake Michigan stretches all the way to the horizon like an ocean. It has to be seen to be believed, and it’s truly incredible. It makes Chicago one of those special cities, like Vancouver and Sydney, where you can witness the power and beauty of nature from the heart of a bustling, manmade metropolis, which I always think is quite inspiring!

Chicago’s Dining & Nightlife

It might feel like a small town sometimes when you’re walking around the streets, but the restaurants and bars in Chicago are some of the most impressive in America. Sure, there are plenty of low-key sports bars and taverns, and mom & pop-run diners, but Chicago has some of the most exciting bars and restaurants that I’ve visited in America.

As a bartender at Fort Willow proudly told me, “Ambitious chefs and bartenders don’t need to leave Chicago anymore.” It’s not just locals who have noticed the shift in recent years, either. The James Beard Awards, American’s most prestigious awards in the food industry, have recently moved to Chicago in recognition of the city’s dynamic hospitality landscape.

My favourite bars in Chicago are tiki lounge Three Dots & A Dash, cocktail lounge The Heavy Feather, gorgeous cocktail bar Machine: Engineered Dining & Drink and newcomer Young American. My restaurant highlights of the trip were fresh, creative and veggie-heavy meals at Ema and Beatnik on the River, and a breakfast at Little Goat Diner.

Exploring Chicago’s Neighbourhoods

Chicago was my first taste of America’s Midwest, which is not known for the cultural vibrancy of New England, the South or the West Coast. That’s not to say there is no regional culture here, but it is a lot more subtle at least to the untrained eye. One thing that I found less enchanting about Chicago was that I felt like most of the neighbourhoods all blended into one. Unlike compact, walkable cities like New York and San Francisco, which have neighbourhoods with visible and distinctive local characteristics, the neighbourhoods of Chicago felt like one never-ending Mainstream American city.

I think also I was a little turned off by how much I needed to rely on Uber to get around, and as a result how much time I spent on the road rather than walking the streets. A flow-on effect of the sprawl, and major roads seemingly everywhere, is that there aren’t many people walking on the street, which for me is a big part of what makes a community feel inviting and friendly. It was always busy on the roads, but so deserted on the footpaths. This is just a personal preference I have for walkable cities with dynamic, personality-filled neighbourhoods, like Melbourne, New York, Paris and Tokyo, compared to car-first cities like Chicago, Los Angeles, Sydney and Brisbane.

Chicago Verdict

I only spent a couple of days in Chicago, so can’t claim to speak with too much authority on the city, but for now it’s a city I’d recommend for a weekend if you’ve already travelled a bit around the US. I’m not rushing back for a weekend with David, but if an opportunity came up for me to visit, I would happily take it – there are so many other parts of the city I’d like to explore, including more restaurants and the Art Institute of Chicago. I’d love to take a locally-guided walking tour too.

I missed the highly visible regional character and flair that shines in my favourite US cities but I admired the beautiful setting, historic architecture in the city centre and really enjoyed the city’s impressive bars, restaurants and craft breweries. Chicagoans were warm and friendly to me during my stay and it is so much more relaxed than New York City, which is nice to find in a big city.

Have you been to Chicago? Or do you live there? Let me know what you think of the city and what you’d recommend I do next time, in the comments.

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