I knew from the time my taxi pulled up to the golden door entrance of the Hilton Chicago that I would like the city. Even classic crooner Frank Sinatra sang, “Chicago, is my kind of town”. What better place to hunker down in a city I had yet to explore then at the historic Hilton Chicago deemed the world’s largest hotel when it opened its doors in 1927, It even had a bowling alley.
All the American presidents since Truman have slumbered at the swanky hotel and world leaders, dignitaries and celebrities frequent the hotel when in town. It still maintains an almost timeless essence. Large palms lilt and grand staircases beckon you to discover more of the hotel’s history.
I lingered in the main lobby with its fabulous montage of movie snippets (all filmed at the renowned hotel), like My Best Friend’s Wedding, Home Alone Two and The Fugitive with Harrison ford. I even had a peek at the exquisite Conrad Suite (named after Conrad Hilton), with its Grant Park views, private Helipad and five thousand square feet of luxury.
Inside the hotel is Kitty O’ Sheas, a quintessential Irish Pub that recently celebrated its 30 year anniversary. Chicago and the Emerald Isle go way back, This is a city that even dyes the river green for St Patrick’s day, so it’s fitting that this favourite local haunt be a part of the Historic Hilton. Kitty O’Sheas is as authentically Irish as possible, even hiring staff from Ireland.
When I pop in for a cold brew I am surprised to learn that they even brew their own beer in Kildare Ireland (the manager’s hometown). I know my beer and from the first sip of the signature Kitty’s Red Ale I was sold. I am told that the food and beverage team scoped out more than 40 pubs in Ireland to ensure that the true Irish flavour was captured. True to the test, the earthy hops infused with Caramunich malt work perfectly.
Kitty O’Sheas even produces its own tequila called Herradura. Again, the food and beverage team were sent on a mission to Mexico with one task – learning the trade of cooking Agave to make Tequila exclusively for the hotel. Herradura is aged in an oak charred barrel for just shy of a year, resulting in a smoky smooth vanilla taste with hints of oak.
Good Ole Chicago Grub
I thought I knew what a good hot dog was – a warm bun, a steamy hot dog with the perfect mix of condiments on top. That was until I hit Portillo’s in Chicago, a staple of the city since 1963 and famous for its hot dogs with a kosher pickle on top (yep, that is how they do it in Chicago).
From my first bite into the steamed poppy seed bun I knew that I would never see a hot dog the same way again. A few locals told me that I had to wash it down with a chocolate shake, or shall I say chocolate cake in a shake (it tastes just like it). Portillo’s is a must do when in Chicago and its true every hot dog for me going forward now has a pickle on top.
Singing The Blues
A short jaunt from the hotel is the famous Buddy Guy’s Legends, a place where “the Blues comes to life on stage”. Legendary Blues singer and guitarist Buddy Guy cultivated his spot as a place where anyone could go and listen to some real good talent. If anyone knows about talent Buddy sure does. With multiple Grammy Awards and having influenced some of the greats from Jimi Hendrix, Eric Clapton and Keith Richards, Buddy Guy reflects just that. All along the walls are signed guitars by BB King, Carlos Santana and Richards and Clapton.
I never knew as I sat down in my much-coveted seat (you have to get there early for a good spot) that Buddy himself would take the stage in an impromptu performance. As soon as he sang just a few notes with that bluesy, electric voice I could feel the tingles up and down my body. Later on, through other sets I could see him sitting in the corner with a grin on his face. I went over to him and we chatted with an almost affable ease. It was only afterwards back in my hotel room staring out at the Magnificent Mile that I realized I had just hung out with the one and only Buddy Guy.