Sat on a metal chair outside a roadside diner, I wasn’t expecting much from the Chicago dog that had been placed in front of me. The fact I was told I ‘wasn’t allowed’ to add ketchup (AKA, my oxygen) didn’t help matters either.

And yet, from the moment I polished off the city’s beloved delicacy (which, to the uninitiated, is a type of hot dog), I was craving another, and raving about it to anyone that would listen.

My Chicago dog experience is a pretty good metaphor for the five days I spent in the Midwest’s largest city.

I’d never been to Chicago before, and aside from it being the birthplace of Michelle Obama, deep-dish pizza, and it’s ‘windy’ nickname (nothing to do with the weather, FYI) I didn’t know much about it.

And yet, by the time I’d left, I’d categorically fallen in love.

Chicago is a haven of arts, culture, and delicious food. The city can lay claim to a vibrant music scene, world-renowned museums, stunning scenery – and a weird number of famous people (Oprah, Bill Murray and Tina Fey to name a few). There must be something in that Lake Michigan water.

So, while Chicago is known as the USA’s ‘second city’, if you’re thinking of a break across the pond, I think it should be top of your list.

Getting across the pond

We travelled to the States with Aer Lingus via Dublin – it might sound like a faff, but this route has the benefit of being able to (quickly) clear American customs in Ireland, meaning we waltzed off the flight in O’Hare as domestic travellers – so no long, boring queues as the jet lag sets in.

It also meant that I was tucked up in my bed in CitizenM Chicago Downtown ASAP. The art-laden hotel was a great base, just a short walk from top attractions. Breakfast was served until a civilised 11am, with hot and cold options, and there’s a bar plus a gym too.

The rooms themselves are small but perfectly formed. An iPad is used to control the lights, TV and blinds – which opened to an impressive view of Michigan Avenue. Oh, and the bed was HUGE.

What to do

With so much to see in Chicago, getting someone in the know to show you around is a good place to start. We went on a food bike tour with Bobby’s Bike Hike with our guide, Jeff (in other words, the nicest man in the Midwest).

We sampled the city’s four main food groups – pizza, dogs, beer and brownies (the sweet treat was invented in Chicago), while also getting a feel for some of the most popular neighbourhoods.

There’s the leafy Gold Coast where you can see the original Playboy Mansion, Wrigleyville – home of the Chicago Cubs and the USA’s second oldest baseball stadium – and the beautiful Lakefront Trail. At 321 miles long, I still haven’t quite wrapped my head around the sheer scale of Lake Michigan – the trail was a great spot for a morning run too.

If you’re a culture vulture, there’s no shortage of museums. The Chicago CityPASS includes prepaid admission to the Art Institute of Chicago – I wouldn’t exactly call myself an art buff, but even I was impressed by the impressive collection of famous artworks, from Van Gough’s Bedroom in Arles, to Hopper’s Nighthawks.

The American Writers’ Museum is also well-worth a visit – catering for all ages, it’s packed full of interactive displays which pay homage to the huge variety of written works, from novels to screenplays, to come out of the USA.

For those who love a good view (and aren’t scared of heights) it would be remiss of you not to take a trip to the Willis Tower (previously the Sears Tower), a 110-storey skyscraper that turns 50 this year. If you’re feeling brave, step out onto The Ledge at the Skydeck – a completely glass balcony where you can literally see the city bustling away beneath your feet.

Oh, and FYI, the first ever skyscrapers popped up in Chicago too. Be sure to get a glimpse at the world’s tallest structure designed by a woman, The St Regis by Jeanne Gang.

And you can’t go to Chicago and not see The Bean, officially known as Cloud Gate, in Millennium Park. The free public artwork was unveiled in 2004, and quickly became popular among tourists. It’s slightly mad, but pretty cool, reflecting the skyline and park surrounding it.

Finally, go to Wicker Park for a mooch around. You can while away an afternoon wondering around this cool neighbourhood full of record stores and vintage shops. Una Mae, Store B and Heaven Gallery had some good finds. The area is also home to the moving Robin Williams mural – guess where the actor is from…?

What to eat

While I’m pretty convinced that no Chicagoans actually eat deep-dish pizza on the reg, it is, of course, one of the city’s most famous exports.

My favourite was sampled at Lou Malnati’s, where the crust was flakey and the pizza was oozing with cheese. I could of course raise the ‘it’s a flan/pie, not a pizza’ debate – but I won’t.

But it was the aforementioned Chicago dog that really stole my heart.

A Chicago dog is serious stuff: the all-beef sausage is boiled or steamed, not grilled. You need bright yellow mustard, and bright green sweet-pickle relish. Then add onions, a pickle the length of the sausage, tomatoes, peppers and celery salt. And you must never, ever, ever add ketchup. It is, quite simply, a masterpiece.

I sampled Chicago dogs at Wrigleysville Dogs, and Superdawg Drive-in. The second spot was my favourite – a family owned old-school diner run by siblings who inherited the place from their parents, Maurie and Flaurie (too cute), who started it in 1948. The restaurant’s menu is pretty much unchanged from when it opened, and was the inspiration for the diner in Grease – the playwrights were from, you guessed it, Chicago. Be sure to order your dog with a malt milkshake and a side of onion chips.

But it’s not all pizza and hotdogs. For Greek-style meze head to Avli on the Park, and for chilled tapas go to Jaleo. I also enjoyed great cocktails at Indian restaurant, Bar Goa (order the Sea Foam).

But by far the best food we ate was at Bronzeville Winery. The Black-owned business is more than just a restaurant – it’s a space to socialise, relax and eat, while listening to the oh-so-cool musical stylings of their regular performers.

Favourite dishes included flat iron steak, seafood gnocchi and oven-roasted mac and cheese.

Where to go out out

From Nat King Cole, Quincy Jones and Earth Wind & Fire to Kanye West, Common and Chance The Rapper, Chicago has gifted us with so many musical talents.

To sample some live music, head to underground cocktail lounge, The Bassment, which offers a busy club room and lively atmosphere. On the night we went, a singer covered a range of hits, from pop bangers to emo. His cover of a Fall Out Boy classic (also from Chicago) was a real crowd pleaser.

Or for blues, go the iconic Buddy Guy’s Legends. Buddy Guy won seven Grammys during his lifetime, and is ranked as one of the greatest guitarists of all time. His club hosts famous and up-and-coming acts seven nights a week.

The verdict

After squeezing in a final few slices of deep dish pizza, I was genuinely gutted to be saying goodbye to Chicago. The city was fun, friendly and full of surprises – I can’t wait to go back.

Getting there:

• Fly from the UK to Chicago via Dublin with Aer Lingus and go through US Customs and Immigration pre-clearance in Ireland. Aer Lingus offers up to 14 weekly flights to Chicago, with economy fares starting from £229 return and Business Class from £1179 return.
• Rates for CitizenM Chicago Downtown start from £132 per night.
• CityPASS is priced at £113 per adult and £87 per child, giving prepaid access to popular attractions, including Skydeck Chicago and the Art Institute of Chicago.
• The Bobby’s Bike Hike, Bikes, Bites & Brews tour, lasts for four hours, with prices starting at £67.
• For more information about Chicago, visit the Choose Chicago website.

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