We woke up Wednesday with no clue of what we were going to do. We sat in our beds and googled “Best things to do in Chicago”. We’d prepared all of the essentials for the trip (plane tickets, game tickets, inter city travel, etc) but did no prep on what to actually do once we were in each city. One common thing that kept popping up on our searches was the Architecture River Tour, so we decided to start with that and just make it up as we go.
After buying $10 daily passes for the elevated train or the “L”, we made our way to downtown. Brent quoted and referenced “The Fugitive” at least five times in the first 30 minutes of being on the train. We got lost for a bit and meandered through the seedy underbelly of Chicago’s lower levels. Not a great place to wander around, but eventually we found the boat dock and went to buy our tour tickets.
When we got to the window at Shoreline Sightseeing, Julie was an absolute delight. She spent about 20 minutes with us and sold us on the “Explore Chicago” pass where you can choose three of over 20 Chicago attractions for a discounted rate. We splurged and did it!
The boat tour itself lived up to the hype. Our guide, Nick, was amazing. A gregarious bear of a man, he was a native Chicagoan and had the smooth voice of an angel. He constantly used words like “confluence” and “verticality” and often asked if we would “indulge him” as he went down a rabbit trail story about Chicago’s history. It was fascinating to earn all about the city and we seriously loved every minute of it. Unfortunately for us, Nick set the bar so high that every other tour guide paled in comparison to him. We joked about inviting him to come to the baseball game with us, but we ended up not doing it. It was our biggest regret of Chicago.
When we got off the boat we headed up the street to a Chicago delicacy, Giordano’s Pizza. It’s a classic deep dish pizza. Sauce on top with cheese and toppings underneath. We honestly didn’t know exactly how to tackle it at first. I am generally staunchly opposed to using a knife and fork with pizza, but I made an exception for my first time at Giordano’s. The food didn’t disappoint, and our only regret was how full we felt for the next 5 hours.
One of the “Explore Chicago” options was to go to the observation deck of the Hancock Building (the 2nd tallest building in the city). The observation deck is on the 96th floor. Julie, who sold us the pass, gave us a pro tip that there is a lounge on the 95th floor and you can go up there for free if you buy a drink. So instead of using one of our three wishes, we could basically get the same experience for the cost of a beer. We are suckers for a deal, so naturally we did it. The Hancock building sits towards the North end of downtown, so the views of the rest of the city and the lake were amazing. Well worth the $10 beer.
We got back down to the street and decided to cruise through the parks on the south end of town. It is home to Millennium Park, the “Bean”, Buckingham Fountain, multiple museums, an aquarium, a planetarium, and Soldier Field. We explored and had a great time wandering around. The city is preparing for the Chicago marathon next weekend, so many of the paths and streets were blocked off, but we had a great time regardless.
The weirdest thing we saw had to be the 30 feet tall video screen fountains that showed zoomed in faces and spewed water out of the mouths every few minutes. Not sure what it was about. Brent, being the mature adult that he is, desperately wanted to get a side picture making it look like he was peeing. Much to his chagrin we didn’t take the picture, but that wouldn’t stop him from more fake peeing antics, but more on that later. J
After exploring the park we headed to Guaranteed Rate Field to see the White Sox host the Indians. All in all we logged over 25,000 steps and 11 miles throughout the day.
We started Thursday with two of our “Explore Chicago” attractions still to use. We did some research on our options and decided for the “Hop-On/ Hop-Off Big Bus Tour”. It’s a double-decker bus tour that makes 14 stops around the city and you can get on and off as many times as you want at any of the stops. We figured it was a good way to see more of the city and get us around from place to place.
As we were leaving our neighborhood we stopped for some breakfast at a great local place called “Batter and Berries”. It’s a tiny hole in the wall place and was rated crazy high. It confirmed Brent’s theory that if a place is less than 18 feet wide, hipsters love it. It was packed and we were lucky enough to get a table quickly before the line started forming. It lived up to its name as the lemon, blueberry, strawberry, and caramel french toast and pancakes were fantastic.
We got to downtown and “hopped on” the bus. The biggest disappointment was that our tour guide wasn’t Nick. Luckily, we got off after a few stops at the Sears (don’t call it Willis) Tower. It was the tallest building in the world for the first 25 years of it’s existence. Now, 20 years after being dethroned, its all the way down to the twenty first tallest building in the world! The observation deck is on the 103rd floor and has 4 recently added “Sky Decks”. They’re basically 4 foot glass boxes that extend out of the building so that you are standing 1500 feet over the sidewalk when you step inside them. They say on a clear day you can see 50 miles in all directions. It was a stunning view of the city in all directions, the lake to the east, Wisconsin up north, Indiana to the south, and the greater Chicago area to the west. We waited about an hour to take pictures in the Sky Deck. I was personally not stoked as we were waiting, but it was worth it. Looking straight down 1500 feet to people walking below with only a piece of glass between you and a 30 second free fall to the street is terrifying and exhilarating.
Brent and I took some standard pictures facing the camera and then did one with our backs turned as we pensively looked out across the land. We weren’t trying to, but the back pictures totally look like we were pretending to pee on the city. Not what we were going for, but funny nonetheless.
Back on the ground, we took the next bus and toured the city for a few hours. Our new guide was a fraction of Nick and just liked to hear himself talk more than anything. We had to get off because Brent was getting too annoyed by him. Experiencing Nick was a blessing a curse.
With only a couple of hours until the Cubs game, we decided to head up to Wrigley a little early so we could walk around the stadium and get some good pictures.
Overall, we absolutely loved Chicago! It’s a young and fun city. It’s easy to get around. It’s clean. We both agree that it’s been the favorite place that we’ve visited on our trips so far. The history, the architecture, the pizza, the sports, the culture, Nick. It really has it all. In total, with our “Explore Chicago” pass, some day long L train passes, and some local tips of how to navigate some loopholes, we saw the whole city in two days for about $100 total. Throw in a coupe of ballgames and Wrigley Field, and we had a blast! 10 out of 10 for Chicago!