My Solo, Impromptu trip to Chicago

As a habitual planner I am always trying to work on my spontaneity in life: reservations don't always have to be made, days don't need to be planned out to the last detail and if things don't work out you don't have to take responsibility for the failed plans' shortcomings. Life should be lived more on the no-plan plan which is something I'm constantly working on. I have had some glimpses of spontaneity over the past few years, but probably the one I get the most reaction from is the trip I booked to Chicago on 6 hours notice... BY MYSELF!

I'd recently been on the job hunt and was looking to change my career. The whole process was emotionally draining and I still wasn't particularly sure I was on the right career path, but despite my uncertainties I had found a job and signed the offer to start on Monday. Before I entered into this new phase of my life I felt like I needed to both de-stress and have a change of scenery before embarking on this new journey.

It's Wednesday night and I'm searching Expedia and Kayak for travel deals that would have me on the beach by Thursday morning. With my friends unable to pick up and go from their jobs and lives, I made the decision to take the trip alone. Limited funds and lack of last minute deals killed my beach dreams, so I started looking at some cities I've always wanted to visit and Chicago came on my radar. The windy city: home to the Chicago Bulls and Cubs, the Magnificent Mile and who could forget Ferris Bueller's famous day off. I was sold and a few hours later at the airport.

I always appreciate a city with easy commute options from the airport. The CTA train takes you from O'Hare Airport right downtown, and it wasn't more than an hour later I was standing on the Magnificent Mile looking at a tree lined lit street that gave me the Christmas feels (and I'm not even a Christmas person!). I'll mention my trip happened in the middle of December and coming from the west coast I found the windy city to be also quite chilly. The trip I booked had me staying at the Hyatt Chicago Magnificent Mile: a beautiful hotel, perfect location for walking distances to museums and attractions along with a king size bed that Kevin McCallister from Home Alone would be stoked to jump on and snuggle up in. I had no time to plan this trip so I hit up the concierge for some tips to start my first night (and the following nights) in the city.

First stop led me to the John Hancock building, iconic to the Chicago skyline standing 1,000 feet above the ground. I was in time to catch the sunset and received a tip that rather than spending the money on the observation deck, head to the 96th floor bar for the same view to be enjoyed with a cocktail in hand. A seat for 1 is no trouble to find and I ended up with an incredible view and met my doppelgänger on the same trip as me. She happened to be starting a job on Monday as well and went on a last minute trip herself! I will recommend checking out the bathrooms at this bar as they have a floor to ceiling window. Needless to say my selfie didn't turn out but still a cool view!

Dinner, for 1. The common misconception when you see someone dining alone is they'd been stood up or are at the wrong restaurant and their 3 friends are next door. My quick research on the restaurant scene led me to The Girl & The Goat, the executive chef had recently won Top Chef so naturally I wanted to see what the hype was about. The concierge politely informed me there was no way I was getting a table there. She recommended Beatrix instead and I couldn't have been more pleased! I opted to sit at the bar where I was confused for a nice man's blind date - it was all going well until the girl showed up 45 minutes late and I basically third wheeled their date and made menu suggestions. I'd recommend the Straight "A" Salad which I re-create at home and the meatloaf (a restaurant fave!).

Three Dots and a Dash: one of the coolest bars I've ever been to. Another recommendation from the concierge, she basically told me to walk down a dark alley for 10 minutes and when you see a torch you'll know you're at the right place. A bit unnerving but I was game! You're escorted downstairs to this room and you're immediately immersed in the feels of a beach side bar on a tropical island. Drinks literally the size of the table and more umbrella drinks than you could imagine. The room is filled with a mix of men in suits and tourists but the vibe is intoxicating. I traded in my usual neat scotch drink for the "house" drink of rum, all spice and something citrus. It was heaven and I was drunk 3 sips in.

Museums! I love visiting museums in new cities, I was lucky enough that the David Bowie exhibit was on at The Museum of Contemporary Art. The man was a legend you really saw how ahead of his time he was, from his persona Ziggy Stardust to his elaborate costumes and music videos. David Bowie changed music and his iconic forward thinking approach to the artistic side of it all paved the way for artists to be able to express themselves through so much more than their music but rather display what music meant to them as artists and how they connect with their audience. The Art Institute of Chicago was another highlight and one I could keep coming back to to fully absorb the monstrosity that is this museum - it is one of the oldest and largest museums in the United States in fact. I won't pretend to know too much about art but I do enjoy wandering the different rooms and era's, noteworthy mentions would be Monet, Picasso portraits, Andy Warhol and the painting that captured Cameron's attention in Ferris Bueller, exhibit A below.

Architecture Boat Tour: A friend had recommended after doing in the summer and I was pleasantly surprised that it was still running in December. We were welcomed with coffee and baileys to keep us warm on the river as we cruised through the city. The architecture was incredible to learn about and the view from the boat offered a different perspective than walking by it. My favourite building was the London Guarantee that stands tall beside the Michigan Avenue Bridge.

Chicago Bulls Game: How could you not go and watch the Bulls play, I mean Michael Jordan played on the same court... a $50 ticket got me a seat at literally the very last row in nose bleeds but it was one of the most fun times I had at a sporting event. I don't think it was a very important game against the Portland Trailblazers that night but the crowd made it feel like it was a game 7 in the play offs. I appreciated the gentleman sitting beside who told me the full history of the Chicago Bull's history as he'd been a season's ticket holder for 25 years. Best. Fans. Ever.

I obviously couldn't leave without a cliche solo photo in front of the giant bean! I'd definitely visit Chicago again as I feel like I just tipped the iceberg with all the fun things to do in this city, next time I want to catch a show at Second City and a Cubs game!

Has anyone else done a solo trip? Where did you go? Would you do it again??