Last minute trips end up being some of the best ones. Which is big of me to admit because trip-planning is half the fun for me. Notes, spreadsheets, Google Docs – I go the whole nine yards prepping for a trip.

But, this trip to Chicago was as sudden as it was fun.

michigan avenue chicago ChicagoTurns out that I am heading back to London after all (ignore everything I said in my last blog post). So, my best friend and I decided to use my last weekend in North America to visit our girlfriend in Chicago. We filled up the gas tank, drove across the border and followed the I-94 all the way to Chi-Town.

When you get off the I-90 Skyway and see the Chicago skyline for the first time, you know you are in the United States of America. Chicago is the quintessential American big city – tall buildings with reflective glass, American flags, busy highways, bustling metropolis. But, it also has a distinct character that sets it apart from New York or San Francisco. Chicago actually feels like a grander version of Toronto – built along the lake, cold, windy and cultural.

Chicago Chicago michigan avenue chicagoWe didn’t have too much time to see Chicago, so we got right down to business on Saturday morning starting at the Willis Tower, fka the tallest building in the world. Have I mentioned I’m not a fan of heights? But you have to swallow your fear and step on the Skydeck glass for the photo opp.

Willis Tower Chicago Willis Tower chicagoWe jumped on the L-Train and went to Millennium Park next where we had way too much fun taking photos of the Giant Bean. Strolling along Michigan Avenue, we arrived at the John Hancock Tower, where we had a casual drink at sundown to check out the shining lights of the Second City.

millennium park the bean millennium park the bean millennium park the bean The Wrigley Building ChicagoAfter the Signature Room at the 96th floor of John Hancock Tower, we had a drink at Three Dots and a Dash, a tiki bar I can not recommend enough. Book ahead though: despite being massive, the place fills up quickly on the weekend.

john hancock sky lounge chicago three dots and a dash chicago three dots and a dash chicagoA couple of other noteworthy spots that I very much enjoyed: The Bristol in Bucktown is a must-visit spot for every foodie; Gather for dinner or brunch; one of the many La Colombe roasters around the city (I went to the Andersonville branch and thought it was hella rad). And whatever you do, don’t leave Chicago without having deep dish pizza.

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