“My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.” — Oprah Winfrey

I’ve had the Windy City in my sights for several years now. When I announced that I had finally booked a trip to the architectural mecca, friends, colleagues, and casual acquaintances couldn’t stop singing its praises. As my wish list of food, sights and shows continued to grow with every passing conversation my only concern was how to fit it all in.

With merely a long weekend to spare, my trusty travel partner, Mindy, and I wasted no time in hitting as many of the cultural and foodie hot spots as possible. Good thing I’m basically an expert at the weekend getaway by now.

We landed at O’Hare International on Saturday morning after a red-eye flight and made a bee-line for the famed Millennium Park with a brief detour past Navy Pier. On our way we passed by Giordano’s and couldn’t pass up the opportunity to finally try the much anticipated Chicago-style deep dish pizza.

We ordered a small cheese and pepperoni stuffed deep dish, which was intended to serve 1-2 people. We were hungry and barely finished half. This stuff is no joke. It was delicious but also not something I’m prepared to eat again anytime soon. Sorry Chicago, but I still prefer New York style.

Next on our agenda was the world-famous Chicago Bean. I’ve been to my fair share of monuments and tourist sites over the years and I was dumb-struck by the sheer magnitude of the crowd. In retrospect, visiting on a sunny, Saturday afternoon on a long weekend in summer probably wasn’t the best strategy for people-free photos. The public sculpture is actually titled Cloud Gate and certainly earns its popularity with its very cool reflective and distorting abilities.

After visiting the bean, we decided to continue exploring Millenium park. We ended up stumbling across Buckingham fountain which I had never heard of before but turned out to be one of the most impressive fountains I’ve seen. And unlike the bean, it was nearly devoid of crowds while offering both stunning lake views and skyline vistas. My favourite surprise of the trip!

From there the only place to top what we’d already seen was to shoot for the sky. So that’s exactly what we did at the Observation deck on the 94th Floor of 360 Chicago. The adrenaline junkie in me couldn’t resist trying out the TILT which essentially involves standing in a window that tilts outwards over the skyline. It wasn’t nearly as scary as the squealing girls riding beside would have you believe. But, if heights aren’t your thing then consider yourself warned.

We also made sure to time our visit so that we would be able to take in golden hour and sunset and even splurged for cocktails – now that’s what I call Happy Hour!

Believe it or not, we managed to fit all of those activities into Day 1 after a red-eye flight. Needless to say, we were ready to call it a night by 9:00pm. We woke up well-rested and ready to take on another jam-packed day.

We kicked off round two with the much touted Architecture Boat Tour. Nearly every single person I spoke with about my upcoming trip to Chicago recommended this tour specifically so we knew that it needed to happen. The people were not wrong. After boarding our open air vessel and toasting with a morning mimosa, we spent the next 90 minutes in the very good hands of the Chicago Architecture Foundation. The tour expertly guided us down all three branches of the Chicago river showcasing more than 50 skyscrapers, bascule bridges, and historic sites along the way. Informative and stunning – this was a trip highlight.

Our next foodie goal was sampling an authentic Chicago-style hot dog. Our vendor of choice was Portillo’s which is known for the local delicacy. This “restaurant” could not be more American if it was located in the White House itself. The americana memorabilia and frenzy of calorie consumption was almost too much to handle but we soldiered on. I wasn’t sure if I could truly enjoy a hot dog without ketchup but the Chicago-original delivered.

In case you’re curious, the ingredients of this particular style dog include yellow mustard, chopped white onions, relish, dill pickle spear, sliced tomato, pickled peppers, a dash of celery salt on a poppy seed bun.

We had just enough time to Uber from downtown to Old Town to see a show by the legendary improv company – Second City. This is the same place where famed comedians Bill Murray, Tina Fey, and Steve Carrell got their starts. The performers we saw had some very big shoes to fill and they delivered a fantastic show of sketch and improv that lived up to its title Fast, Loud, and Funny. 

We took the scenic way home along the beach to dip our toes in Lake Michigan. I still can’t believe that it’s a lake and not the ocean. This is a seriously photogenic city and so much more than just the home of Oprah and Obama.

As the weekend drew to a close we knew we hadn’t seen it all. With more time I would have loved to check out a jazz club and taken in a Cubs game at Wrigley field. But, I always like to leave a few activities still on the table because then I know I’ll have to come back again. I’m not finished with the Windy City yet.