[Chicago, IL]

Kristina did not know this yet, but sightseeing with me is no joke. There are places to be seen and meals to be eaten and pictures to be taken. I have a checklist with must-dos and nice-to-dos, and I have google-mapped the place to death because my worst nightmare is wasting precious time trying to figure out where to go next, or, even worse, having to come back to an area I’ve been to already to do something that was on my list that I didn’t realize was nearby.

I also like to know where I am going. To this end, I fired up Waze (a navigation phone app that utilizes user-reported traffic bottlenecks to reroute the rest of us through less congested streets) as soon as we left the house at 8 am. We were bracing ourselves for rush hour traffic from the Northern suburb of Skokie to the city center, where our Chicago Architecture Foundation boat tour was set to start at 10 am. Kristina wanted to take her usual route downtown via the Kennedy Expressway, but Waze was not having it. In the end, we cut east on Hwy 14 and ended up catching Lake Shore Drive from its Northern-most tip. Traffic was still heavy but we had a fairly smooth ride all the way downtown while checking off a must-do in the process. Lake Shore drive was beautiful. All development was on the West side (to our right), keeping the views of Lake Michigan to the East (our left) nice and pristine. It was a beautiful sunny day, and we were happy that the nightmarish drive we were expecting did not transpire. Thank you, Waze!

We parked at Millennium Park, then walked up a few blocks to the corner of Wacker St and Michigan Ave.

We were right smack in the middle of downtown Chicago, and I was already overwhelmed by all the magnificent buildings around me. Our tour by the Chicago Architecture foundation, a recommendation I’d gotten from just about any of my friends I’d asked, was just amazing. It lasted an hour-and-a-half, it took us under 25 of the many bridges connecting the banks of the Chicago river, and it gave me a great appreciation of the wonderful architecture of this great city. Just about every building we went by on either side of the river was designed by some powerhouse architecture firm or person, and unique design features complemented the surrounding structures while giving each building its own distinct flair. Different time periods and architectural styles work effortlessly together, and no two buildings are alike – unless it’s by design, of course. From the choice of windows to exoskeletons to curves matching the bends in the river to honeycomb shapes, these features are what make the Chicago skyline like no other. I found myself taking an enormous amount of pictures because every different angle revealed something else about the same building, or it allowed me to combine it with its neighbors in a uniquely framed shot. I got to see many of Chicago’s most famous skyscrapers on this tour – Willis Tower (formerly Sears), Trump (which I’d already seen from the street but we had better views on the tour), 311 S. Wacker, the Merchandise Mart and the Chicago Opera. Not only that, but our luck continued here with the weather – despite the occasional wind blast, the sun kept us somewhat warm and we were comfortable being outside in mid-40s temperatures (that’s 7-10 C).

By the time we were done with the tour, lunchtime was fast approaching. I had noted Lou Malnati’s as a must for a Chicago deep-dish pizza. We found a location nearby but it was just a bit too far to walk (remember, I don’t like wasting time!) so we hopped in an Uber to get there. Already impressed with the Waze experience, Kristina’s jaw dropped when I told her I’m about to summon my private driver to take us to Lou Malnati’s (for those outside of US or others who don’t know, Uber is another smartphone app that connects private car owners with others who need a ride around town. It’s very much like a taxi service without all the hassles of taxis. Uber’s motto is that it’s “Everyone’s private driver”). We were at Lou Malnati’s in no time, and things kept working in our favor just as they had on the drive into town. The place was not busy yet and were able to grab a table by the window, but it quickly filled up about 20 min after we got there. We had the most divine pizza experience of our lives at Lou Malnati’s. We ordered “The Lou”, which is a deep dish pizza full of awesome veggies like spinach, mushrooms and tomatoes, all wrapped up in a delicious garlic bread crust. We added sausage to the mix to make it a little bit more hearty, and we ordered the small size to share. When the pizza arrived, we both thought it was very small and might not be enough for the two of us (although we were both too embarrassed to say that), yet we quickly realized this baby was filling. Deep dish pizza is no joke!!! It was so yummy though, we just kept eating. 🙂

Another quick Uber ride later we found ourselves at the John Hancock tower. When it was finished in 1968, the John Hancock was the tallest building in the world outside of New York City. It is currently the 4th tallest building in Chicago (after Willis, Trump and Aon) and the 7th tallest in the USA. The Signature room at the top was recommended by a friend, who warned that dining there is overpriced for the (lack of) quality but the view is amazing enough to grab a drink. Things worked out nicely for us yet again and we ended up with a table right in front of the window overlooking Chicago to the South. Magnificent Mile, Willis Tower and all the other magnificent buildings in this city were laid out in front of us. Service was almost non-existent but we managed to grab a couple of coffees nonetheless, and after snapping a couple of photos we set off on foot to explore Magnificent Mile.

The Signature room at the 95th floor of John Hancock

Another view of the Navy Pier

Nice lunch view at the John Hancock tower

Looking 95 floors down

The Signature room at the 95th floor of John Hancock

The Signature room at the 95th floor of John Hancock

Magnificent Mile is an upscale section of Michigan Avenue. I found it very similar to 5th Avenue in New York, Vitosha Street in Sofia or Third Street Promenade in LA. Kristina and I did a bit of shopping, and she ended up with a pair of sunglasses very similar to mine from Ann Taylor Loft – something that proved important later when were taking selfies at The Bean.

Magnificent Mile

Magnificent Mile

Magnificent Mile

Anyway, we strolled down all the way to Millennium Park, but not before getting some milk-covered caramel crisp popcorn to snack on from Garrett Popcorn Shops. We sat on a bench at Millennium Park and admired the beautiful weather and the buildings surrounding us. And then we went to The Bean, and that’s where the shenanigans began.

The Bean, or Cloud Gate as it’s officially called, is a sculpture with a highly polished exterior which reflects and distorts the city skyline. It’s very popular due to the unique photo opportunities it provides. Kristina and I set out to get a few good photos, but perhaps because we were both wearing sunglasses or because it’s hard to tell on my camera digital display, we were not satisfied with any of the photos we’d taken. So we took more. And more. We even took a cue from another group of people nearby and got down on the ground. Yes we did. However, when we got home and took a look at the photos, we were surprised at how well they turned out! I cannot look at all of our photos without starting to laugh – we had such a fun time trying to get some creative photos at The Bean! This will be a Chicago memory I will cherish.

The Bean! It’s actual name is Cloud Gate.

To finish off the day,we walked around Millennium park and even strolled down to neighboring Grand Park to check out the Buckingham fountain, which was, unfortunately, not in service, perhaps due to the cold weather.

Lurie Garden near Millennial Park

It was getting late and we wanted to spend the evening with Kristina’s family, so off we went. Once again we hit rush hour, but our luck had run out. Getting out of downtown was just an abysmal experience. Turning left on the street we needed to be on was an almost impossible task, as the people who were crossing the intersection in front of us did so even when there was no room for them on the other side, blocking both us and oncoming traffic. LA may have bad traffic but driving courtesy is fairly commonplace, and I had not seen disrespectful driving like this in the US, ever. Even as drivers got stranded in the middle of the intersection for almost the entire time our light was green, those behind them took no notice and just kept doing the same thing. Kristina lamented about the bad driving culture here, her comments very much in line with earlier observations she’d made about how stressed out, rude and self-serving people in Chicago are. It made me thankful for my laid-back, sun-worshiping, drought-ridden state of California.

Despite that momentary frustration, my first day in Chicago was amazing. I can’t wait to explore more. And maybe even take some more selfies at the Bean.