Saul Bellow was a comedian with Chicago. The Nobel and Pulitzer Prize-winning author seemed to love and loathe the midwestern city with equal measure — ‘in Chicago you become a connoisseur of the near-nothing’.

Bellow, who passed away in 2005, said that he didn’t see life the same way in Humboldt Park where he was born. Many of the city’s nearly three million inhabitants might be inclined to agree with the latter.

Chicago’s view of Lake Michigan has been called “Chicken on the Shoulder”. However, I feel the irreverence and joy in having the last laugh at New Yorkers and Californians who are prone to looking down at the rest the country.

The Daily Mail's Hugo Brown says Chicago’s lakefront was dotted with runners and cyclists enjoying the last gasps of bearable weather

The Daily Mail’s Hugo Brown says Chicago’s lakefront was dotted with runners and cyclists enjoying the last gasps of bearable weather

CHICAGO’S MOST IMPORTANT TICKETS

THE LEDGE

The 103rd Floor of Willis Tower offers the most spectacular views of the city. The Ledge’s glass boxes extend 4.3 ft out from the Skydeck and a fifth is opening soon. (theskydeck.com)

THE MAGIC LOUNGE

This Andersonville spot combines magic theatre and speakeasy. It offers tableside entertainment with dinner. Book at chicagomagiclounge.com.

MUSEUM OF Illusions

Six days before lockdown began, the museum was open. It is an excellent place to spend a few hours looking through some strange illusions and exhibits. (museumofillusions.com)

ART INSTITUTE

The flagship exhibition at the Art Institute of Chicago by Barbara Kruger is entitled ‘Thinking of you. I mean me. I mean you’. (artic.edu)

The lights have been turned back on throughout the city. The downtown theatres bustle and the L train rattles overhead. On the 18-mile Lakefront Trail, cyclists and runners are enjoying last moments of mild weather.

Amy Lawless (from Galway) runs The Dearborn restaurant. It is her sister Clodagh’s business. They moved to The Dearborn 22 years ago.

Covid’s disruption is still nothing to the damage caused by 1871’s fire, which rebuilt the downtown. This I learned from Adrianne the guide for the CAFC River Cruise. It was an architectural boat tour.

The oldest building we see dates from 1898, around the time Chicago hoped to become the ‘Paris of the Prairie’.

These twin peaks, the Wrigley and Tribune buildings (neither of which are houses anymore), mark the beginning of the tour. I hear a couple behind me ask aloud why the Tribune needed such a big building: ‘Probably for back when people bought newspapers’ is the conclusion one of them reaches.

We pass sleek Art Deco towers as we glide down the river, flashing postmodernism, and glowing late modernism. This is the best way to view the city.

It also gives me a different perspective on The Pendry, a 364-room hotel which opened in the summer, where I’m staying. To resemble champagne bottles, the 1929 Art Deco building had black granite, green Terracotta and gold leaves.

On a West Loop food tour, David, our guide, mentions again the fire and tells us that the city is proud to have seen its revival. It’s why the local soccer team is called Chicago Fire.

Although many people are critical about Chicago’s urban environment, David is among the Chicagoans who feel almost humbled to have lived here. He also has a wealth of knowledge that reflects this. He explains to me the importance of the big three — deep dish pizza, Italian beef sandwiches and hot dogs.

Because Oprah Winfrey opened her first studio in West Loop back here in 1988, West Loop has many restaurants. I sample meatballs from Nonna’s, a Do-Rite doughnut, caramelised chicken dumplings (Urbanbelly) and some delicate chocolates (Bad Bach). Most importantly though, pizza from Bonci’s — not deep dish but Roman style, twice-cooked, crisp — the best I’ve ever tasted.

Rose Mary serves small plates, but it’s a Chicago-sized restaurant. It’s Italian-Croatian — rich and clever — that kind of uniquely American combination.

Each neighbourhood serves a purpose — West Loop for restaurants; Pilsen has a large Mexican community; and Andersonville was originally Swedish. There’s a communal and small-town feel to the latter, and it’s popular with the LGBTQ+ community.

One evening I head to Buddy Guy’s Legends blues bar which affords an appearance from the man himself, who inspired the Rolling Stones (essentially the band copied Chicago’s style of electric guitar blues).

He does a set somewhere between comedy and blues, and ad-libs singing ‘I’m a king bee’ and ‘I got a woman who’s big and fat’ — warning us this isn’t music for the radio any more.

Pizza perfection: Hugo went on a food tour of the West Loop neighbourhood and had some of the best pizza he's ever tasted (stock image)

Hugo had pizza perfection. He went on a West Loop food tour and enjoyed some of the most delicious pizza he has ever eaten (stock image).

West Loop is packed with restaurants partly thanks to Oprah Winfrey opening her studio here in 1988

West Loop is jam-packed with restaurants thanks to Oprah Winfrey’s 1988 opening of her studio.

Comedy club The Second City is worth a visit, too, with its oft quoted alumni — Bill Murray, Tina Fey, Catherine O’Hara. Improv can be hit and miss but surely that’s the nature of the game.

An afternoon should be spent strolling in the $500 million Millennium Park, seeing the optical sleight of hand that makes Anish Kapoor’s Cloud Gate (The Bean) so popular, and the Art Institute.

There’s a striking exhibition on by Barbara Kruger, but the most famous painting here is likely Grant Wood’s American Gothic (although I prefer its neighbour The Artist Looks At Nature by Charles Sheeler).

Rock on! Hugo watched Buddy Guy, who inspired the Rolling Stones, perform at his popular blues bar Legends

Go on, rock on! Hugo watched Buddy Guy (the inspiration behind the Rolling Stones) perform at Legends blues bar.

An afternoon should be spent strolling in the $500 million Millennium Park, says Hugo. Pictured is the park's Cloud Gate sculpture

Hugo says that an afternoon could be spent wandering through the Millennium Park worth $500 million. This is Hugo’s Cloud Gate sculpture. 

American Gothic, in all its despair, seems to be a representation of the wild struggle to survive in frontier life during the push west. And that’s why there’s an innate comfort in the Midwest — the name creates distance from the boundary, and this is aided by the authenticity of its inhabitants.

After three days of wind, atmospheric snow and thick clouds, I finally see the sun in my last afternoon. The downtown glows, and Lake Michigan shows its true colors.

Saul Bellow’s comment makes more sense to me now. Chicago does make life seem clearer when it is sunny. And if there’s one thing that can be learned from the generosity here and healthy Chicagoan pride, it’s that we should all reconsider the way we view our own hometowns and perhaps appreciate them more.