Winning the Windy City

                The excitement was palpable as landed in Chicago. This was a trip I’d been looking forward to since my birthday in January. I had torn open some wrapping paper and found a ticket scrapbook (which was great since I collect ticket stubs), but the present went from cool to amazing when I noticed there was already something in one of the plastic sleeves. It was a replica of a ticket letting me know I would be in attendance for the Chicago Cubs opening day game of 2015.

                 Arrangements were made for us to arrive early Saturday morning in Chicago, the day before the game, and fly home Tuesday, giving us both room to attend a rainout date in case we encountered bad weather (always a possibility in Chicago) and to get some quality time in with my favorite city. There is something about Chicago that gives me a lot of positive energy. It just seems to have a rhythm and pace that fits me perfectly. The early arrival gave us just about the entire Saturday to work with, and we went about making the most of every minute of it.

                This is about how we won Chicago for a day.         

                We flew into Midway airport and took the Orange line train downtown. The train was clean and quiet, and even had free in-car entertainment when a Korean man stepped on at one of the stops wearing headphones and proceeded to sing and dance the rest of the way to what seemed to be a pretty catchy Korean tune. I couldn’t even hear the music and I was humming along by the time he got off.  He wasn’t looking for attention or money. In fact I can’t even say for sure he was aware he was on a train with other people. But we were off to a good start.

                We changed trains in the Loop, which involved hauling our suitcases up and down narrow metal stairs and through turnstiles. This wasn’t easy, so we decided to reward ourselves with breakfast at Ann Sather, a restaurant just across from our Wrigleyville hotel featuring tasty omelets, scrambles and most importantly delicious, gooey, hot cinnamon rolls the size of your face.

                With a severe sugar rush firmly taking hold, we waved down a cab and told him to head for the river just off Michigan Avenue. Back at the airport I killed time waiting for our bags by calling one of the companies that does river architecture tours. I asked if we needed to make reservations or buy our tickets over the phone and was told “Oh there’s no need. We really don’t get busy until it gets hot out, so you can come on down.” Perfect. The weather was sunny and cool, excellent jacket weather that lined up well with cruising the river looking at Chicago’s gorgeous skyline. So we headed to the dock and were promptly told the noon tour was sold out. Well, crap, so much for not needing reservations. They were selling tickets for a later tour, though, so I bought a pair and we found ourselves with a few hours to kill.

                One thing we had not done yet on any of our trips to the city was go up to the observation level at the Willis Tower. That sounded like a good idea on a sunny day, so we hopped in a cab (I love how easy it is to find a cab in Chicago) and headed for the Tower and its glass-bottom walkway. As it turns out, we weren’t the only ones who had this idea. The line was around the flippin’ block. Literally. It went out the door that led to the elevators, snaked to the sidewalk, continued around a corner and as far as I know stopped just across the Iowa border. So far our plans weren’t working out like we’d hoped. It was time to improvise again. Our cab driver was on his game though, and recommended we go to the Hancock building instead, then head up to the 95^th floor to the lounge. The observation deck is one floor higher and costs $18 per person. The lounge doesn’t cost anything, is only one floor lower, and sells booze. Sold.

                Sipping cocktails and looking out the windows at the skyline only made me more eager to take the architecture tour. The mix of modernist and art deco buildings stretched out before us in the sun, so we relaxed and watched the lounge host scramble. Now that man is a problem-solver. It seemed everyone in the place slipped a bill in his hand as they walked in, sending him scurrying around the place to find a window-side table. We were happy with our slightly-elevated spot, which allowed us to look over everyone and still see out, but so I was able to see the action. My favorite move of this was to see him sit people at a table across the aisle from the window tables and make sure they got a round immediately. Then when any table-siders made a move for the door, they were barely out of their seats before the table was cleaned and prepped before ushering the party from “window standby” to their spot by the glass. One table being used as a “window waiting room” must have seen ten different parties in an hour. I was getting worn out watching the guy.

The view from the Hancock

                The time passed quickly and we were soon back in a cab heading to Michigan Avenue to catch our boat tour. This particular company does two different tours, one that goes out on Lake Michigan and cruises up and down the coast and another that focuses on the river. Ours was the more river-centric version, so with some Chicago blues music playing over the speakers we and about 200 others set off. The tour guide was on the microphone soon explaining the history of the buildings as we rolled by. He was engaging, entertaining, funny and seemed to have tremendous knowledge. I can’t say enough about how much we enjoyed this tour. The views were amazing and it was intriguing to see the different eras represented in what loomed above us, first in the older buildings that featured the river, then the buildings from the 70s and 80s that turned their backs to the river, before the water views became popular again in the 90s and 2000s. Plus, the sheer size of Merchandise Mart still astounds.  At one point it was the largest building in the world in terms of square footage. It’s a classic bit of art deco that I never thought looked very good, but I heard a new perspective on it. “It’s just so…precise,” was the description that really hit home. Then I realized what Merchandise Mart truly represented – a triumph of OCD-level precision architecture. It made me look at it differently and appreciate it a bit more.

Best skyline in the world 

Chicago's architecture is fascinating and beautiful on a sunny spring day

The enormous Merchandise Mart

                Once the tour was over we headed back up to Michigan Avenue to the Tribune Building. This place has an interesting feature: chunks of  other famous buildings are incorporated into it. For instance, walking around the building you will see bricks that have bits of the Roman Colosseum, the Parthenon, the Great Wall of China and others cemented in. It’s fascinating, and I’m sure some of them were even taken with permission. Maybe.

                The next stop was a store that just caught our eye strolling the Mile. It was Dylan’s Candy Bar, a two-story candy shop that seems to have every kind of hard candy and chocolate known to man or woman. They even have old-school ones I didn’t know they still made, and the place is laid out with a spiral ramp up to the second floor, bright colors and a happy vibe that makes you feel like you wandered into Willy Wonka’s place. We tried a few exotic chocolate bars there for dessert later. But first, we had pizza to eat.

                Lou Malnati’s was our choice. Sure, Giordano’s and Gino’s get more publicity but we both really liked Lou Malnati’s pizza. They also had a spinach-cheese stuffed bread as an appetizer that we both loved. The pizza was hot, thick, stuffed with toppings and delicious, and that’s coming from someone who doesn’t care that much for pizza. We finished off our carb-fest with a chocolate chip cookie cooked in a pizza pan (similar to the BJ’s Brewhouse pizzookie) that was mouth-watering. We were stuffed solid, but very happy.

                Loaded with bread, cheese and sugar, we were left with energy to burn as night fell. We had been to Second City in the past, and their show on this night was sold out, so we looked for an alternative. We decided to head to the Laugh Factory on the northside, a short ride from the hotel. They had a late-night showcase, so we got to see eight different comics do a few minutes each. I would say seven of the eight were outstanding. It shows just what kind of talent there is in Chicago that on a showcase night there were that many hits with only one miss. The room was loud and enthusiastic, and by the end our faces were aching from the smiles.

                After all that, we went back to our room and collapsed. It was an amazing day, and we still had the main point of the trip to come: Going to Wrigley Field on Opening Day. But we ended day one with confidence we’d taken full advantage of the great city of Chicago.