The first and only ever time I was in Chicago was with Shane back in 2014, just before we moved to the Netherlands. We were there for our friend Brian’s 30th birthday, and the only thing I really remember is that the famous Bean was right next to our hotel. That, and we all went out for massages. It was my first one ever (at 28 years old), and while everyone else came out relaxed, I was disappointed. I remember sitting there listening to “oh! and when they did this and that!” and thinking “I got none of that!”
Needless to say, I was excited to see Chicago again. Plus, the Wolfpack (Shane, Brian, and me) hadn’t been together in roughly three years.
So, we spent our final few days in America letting Brian and Shannon tour us through some new and some of their favorite spots. I won’t lie, the itinerary was ambitious and involved pre-made Google maps. We didn’t make it all the way through, but we did our best!
To be honest, this lasted for about 10 minutes. It was a beautiful idea, but the weather just wasn’t cooperating. However! Shane and I did put our feet into (very cold) Lake Michigan while Brian and Shannon held down the blankets… literally. It was that windy.
We walked it. We biked it. We took cute pictures.
The Starbucks Reserve Roastery!
Maybe this is an unpopular opinion, but Starbucks isn’t my favorite. I would have never thought to visit the roastery. However, if you like coffee, then I would absolutely recommend a visit and a tour! I didn’t realize that Starbucks had a reserve coffee line, and I definitely didn’t realize that there were only six reserve roasteries worldwide!
If you want to just have a coffee and experience the place, then it’s free, but we did a tour of the four-story Starbucks with a coffee tasting that goes in-depth into their coffee process, from beans to brew! You won’t leave un-caffeinated.
Oh, and their espresso martini is not to be missed! Yes, this Starbucks has a bar.
Chicago was a surprisingly bike-friendly city, at least the little bit of biking we did. The biggest difference was the turn signals or the lack thereof. Here, sticking an arm out when you’re turning left or right is engrained, but Shane and I seemed to be the only ones giving turn signals in the city.
We hit the Lakefront Trail towards the end of the day, which had spectacular views! It’s a walking and biking path, so I highly recommend it.
We hit several rooftop bars in between stops for tacos and ice cream. I’m a sucker for a good view. So, my favorites were The Robey (which had the tiniest rooftop pool I’ve ever seen) in Wicker Park and The J. Parker in Lincoln Park (which had a bonus city + lake view)!
360 Chicago (the John Hancock Tower)!
If you’re looking for an incredible view, then the 360 Chicago observation deck is the place to be. If you want to enjoy that same incredible view with a semi-overpriced cocktail, then you should check out the Signature Lounge on the 96th floor. I say semi-overpriced because for the price of one admission to the observation deck you can get two fancy cocktails with a great view (although not 360 degrees). Since we went at night, we decided on the cocktail option.
Like I said before, we had an ambitious list that went partially unfulfilled. Guess that means there’s gotta be a next time!
We’re on the final countdown, folks! Two weeks from now, we will be on the way to Ecuador!
Until then, we’re cramming in all the Munich we can handle.