Chicago

Considering I grew up a short 4-hour car ride from the vast metropolis that is Chicago, I'd never really been to see what it had to offer.  During college, my friends whisked me away for a weekend trip but since I was mid-long-distance breakup, all I can remember is seeing signs of the British everywhere: flags, food and even an Austin-Powers impersonating busker. I kid you not.

Years later and with this in mind, Paul, the shiny new British boyfriend, my brother, his girlfriend, Catey, and I bundled into the car to enjoy a weekend of everything that Midwest charm dared throw at us.

It did not disappoint. We lodged ourselves at the Holiday Inn about the Chicago Sun Times Building, right on the edge or middle of everything, depending on how you look at it. Being Paul's first American city, he spent much of the weekend gape mouthed staring up at the El train muttering to himself about how much it actually looked like TV.

This is before we fed him. Deep dish pizza, pancakes and breakfast burritos the size of our heads, it all felt a bit beyond belief. I mean, Chicago style deep dish pizza itself will make a heart surgeon rich. We also stumbled upon a delight of a restaurant, entitled Brunch, which served everything in heaping quantities. The red velvet pancakes coupled with Jody, our sassy waitress who announced herself in the third person every time she came to check on us, 'Jodaaay's Back!' meant we became repeat customers.

And from there we wandered past many of Chicago's icons. After refusing to wait for hours at the aquarium, we took to bicycles along Lake Michigan shoreline and passed Anish Kapoor's 'Cloud Gate' known fondly as The Bean. Tens of oddly angled photographs later, we wandered towards Navy Pier, home of tat, tack and the memory of America's first Ferris wheel, a homegrown product unveiled at the World's Fair in 1893.

Wending our way up Michigan Avenue and through the back streets behind our hotel, we found Redhead Piano Bar, a buzzing, atmospheric place, that we needed to go in. Unfortunately, Paul was poorly attired in a pair of tatty white Converse and before the bouncer could get another word beyond 'we have a footwear policy', I beseeched him to point us in the direction of another piano bar, another place for a drink, another respite from the blustering city winds. The bouncer interrupted the mumblings of a madwoman with the epic: 'Sir, you can come in but you'll have to trade your pair for some loaner shoes.' Which is when he led us to the janitor's closet where row upon row of tailored men's loafers in all shapes and sizes were housed. So Paul took the loaner shoes and we took our seats in the dimly lit, red carpeted, once smoky environs of this palace of music.

I don't remember if the piano bar was particularly good. It doesn't matter; the place had a loaner shoe policy and that was enough.

The remainder of the weekend passed in a blur of walking, wandering and hopping on the city's Architectural Boat Tour, which sounds a lot more boring than it actually is. Actually, it became a highlight. We zipped in and out of various districts in the city, learned about the elaborate process of dying the river green for St. Patrick's Day and even glided past the building a car shot out of in an elaborately stunted television advert. The cruise prompted both Paul and I to pick up The Devil in the White City, a harrowing non-fiction split narrative about the bringing of the World's Fair to Chicago timed impeccably with the rise of America's first serial killer.

The weekend passed far too quickly and we sadly bid adieu to the Windy City, a gem found far too late in my once-Midwesterner life. If that were the end, it would have been a blissfully perfect weekend. Clearly, we decided to tempt fate by taking the Amtrak back to Royal Oak, advertised as a pleasant four-hour rail journey. Jeff and Catey made their way to a friend's wedding so Paul and I sojourned across town to find the train station. This took longer than it should have.

And if there's one thing I have learned about Amtrak, it's that everything takes longer than it should have. Trying to find a ticket counter, trying to find a waiting room, trying to find a platform, trying to will the train to move quicker than at a slow jog. Trying, trying, trying. In the 'snack bar' selling White Castle-style hamburgers and cardboardy pizzas, Paul was given advice by the train attendant: 'Keep one book for the tax man and one book for yourself. That's how you live this life.' He didn't know anything about the train except that for purposes of not breaking sound ordinances, it wouldn't move over 10mph in large swathes of the route.

Eight and a half hours after we left, we arrived in Royal Oak where my mother and sister had been waiting for hours. Fail for the great American railways. But Chicago, it's winning.