Bobby Pawar in thrall of the buzzing streets of Chicago

Why: People mostly see Chicago as a windy town in the freaking Midwest. But it’s a great city and an architectural gem. The Chicago River runs through it and beautiful bridges cut across the waters. The city’s on Lake Michigan with sandy beaches and actual waves and it’s so damn big, you can’t see the other side.
Just don’t pop by in winter months. Come summer, the city blossoms. There are street festivals – food, art and music, everywhere. Upcoming bands play in the parks, the marina is abuzz and the sail boats come out. It’s also America’s Blues capital.

My first time: The day turned out to be the coldest of that winter. I arrived in a jacket bought in New York. There were some cool jackets that I liked, but the old store-manager said, “Son, those are spring coats. You are going to kill your wife and yourself.” So I let him pick out my clothes.

In Chicago, my partner taught me how to spot a tourist. He said a local would never stand close to the edge of a pavement or on a curb because a sudden gust of wind can blow you off and straight into the middle of the road.

Go with the wind: You meet incredible characters in Chicago. The mailroom guy at the agency I worked in was a member of three different bands and had a gig practically every day.

I met a 70-year-old Jazz man with a constant tremble. But once he stood up and played at Shaw’s Crab House he was rock solid. One of the most amazing Blues singers I’ve heard is a 50-year-old woman, she’s hurricane on stage.

The 24-hour layover: Start the day with a river boat tour to see the city’s architecture. Go on a bus tour of Chicago’s underworld, visit Al Capone’s old haunts and mob sites like the spot of the Saint Valentine’s Day Massacre. Have the lamb chops at Indian-Mexican restaurant Vermilion behind the Wrigley Building.

Catch some stand-up comedy on Wells Street. Or head to South Wabash, the theatre district. Boystown is a gay neighbourhood that has some cool, quaint shops. Chicago’s jewels, however, are its great Blues bars -Chicago Blues Bar, Kingston Mines and Buddy Guy’s Legends.

Seven days and nights: If you are an early riser, go to the beach and walk down Michigan Avenue. Go to the promenade for a stroll and feed the ducks. Try some of the best sea food in the world at South Water Kitchen, Shaw’s Crab House or Sweetwater Tavern & Grille. For a French-Vietnamese feast, go over to Le Colonial.

You can’t miss it, just look out for the Bentleys parked outside. Reserve a table 30 days before the dinner date. Drive down to Ann Arbor for great sailing. Take a two-hour flight to Colorado Springs. Go down to the universities or drive around the $40-million-home towns. Take the ‘L’ train, the track has no railing and you feel the train will fall off at any moment.

Tips for the good-time traveller: Chicago has way more single women than single men. So the odds are in your favour. One of the city’s proud sons, Hugh Hefner developed the idea of Playboy here.