My Kind of Town, Chicago Is . . .

That's the Sinatra tune my son has been singing to himself since we returned from the Windy City a few days ago. And after four days of pounding pavement and riding trains, seeing all the nooks and crannies Chicago has to offer, I can't say I blame him. Whatta town . . .

Prior to our visit and subsequent immersion, I had (and wrote of) a fair amount of anxiety I was feeling about the thought of my oldest child Drew alone in an unknown metropolis. Besides, this was my first real visit too. Some of that was irrational but a good deal of it was warranted. Chicago, after all, is a bustling, active, figure it out for yourself sort of city.

So that's what we tried to do.

Day One: To my pleasant surprise, Chicago is barely a seven-hour drive from the Twin Cities. Looking at a map, I knew that objectively - but it was reassuring for an anxious parent like me. Driving in Chicago - like any other metro area - is a pain, so we parked the car in a ramp for the duration of our trip (I was never worried about the car - it's not worth stealing. In fact, I was a little disappointed when I saw it untouched the day we left). Our hotel was in the Lincoln Park neighborhood, about a mile south of Wrigley Field. The first night we walked about eight blocks north on Clark Street and two blocks west on Belmont Avenue to Giordano's Pizza. I was struck by all of the people out and about, and thinking, "is Drew going to be okay amidst all this humanity?"

Day Two: I was up early because I wanted to go for a run. Our hotel was about a half mile from Lake Michigan, so I headed due east. When I hit Lincoln Park and its running/biking paths, I was again stunned by all the people, not to mention the amazing view of the downtown skyline. After a few starstruck minutes, I began to relax. Running like a native, I realized, was helping me acclimate.

Our first stop that morning was a 10:00am scheduled tour of Loyola University, just a short three mile train ride north of our hotel. If only it had been that simple. You see, riding the "L" (elevated train) was my biggest concern. Not the riding itself, but getting a handle on its schedule, transfer system and color-coded map. So, not surprisingly, that morning's search for a station was a bit of a circus. Map in hand, I managed to get us good and turned around in short order. And, being a male, I never considered asking for help. Instead, I let the expletives fly. Who should come to the rescue but Drew, who easily walked into a neighborhood store, asked a clerk for directions and emerged sixty seconds later - problem solved. I was humbled and also getting a sliver of reassurance that my son just might be able to take care of himself in big, bad Chi-town.

The Loyola tour was a huge success. After two short hours was son whispered to me, "Can I just skip my senior year and start my life right now?" And who could blame him. He was outwardly keeping his composure, but I could see the possibilities opening up in his mind and all over his demeanor. Consequently, his comfort level increased my own.

Loyola completed, we took a long train ride to the University of Chicago, quickly realizing it was not a school Drew would feel comfortable attending. Nuff said - lesson learned. So instead, we headed downtown.

Chicago's Loop is absolutely alive. The Gold Coast, Magnificent Mile, Michigan Avenue, Navy Pier, Millenium Park. We took in as much of it as our aching feet could stand. And when we could no longer stand, we rode an elevator 96 floors to the top of the John Hancock Tower to take in the incredible downtown views. Drew seemed unaffected by the height, but my daughter and I laughed nervously every time we got too close to the floor-to-ceiling windows of the observation deck. Worth it. Day Two was a huge success.

Day Three: I wanted one of our days in Chicago to be tour-free. My reasons were entirely selfish - I wanted to see Wrigley Field. But before the 1:00pm game, we managed to squeeze in two activities. Drew joined me for a run of the same route I had taken on Day Two and was able to see the city and its people in the same perspective as I had the previous morning. After our run, he said he wanted to go back up to Loyola to buy a sweatshirt. After making the usual parental objections ("you're not a student there yet"), we hopped on the train (with no wrong turns), wandered the campus a second time and found the bookstore. After making our purchases (I had to successfully talk myself out of buying a Loyola Dad coffee mug - "he's not a student there yet"), it was on to Wrigley. Without rambling on like a ten-year old boy for the next four paragraphs, I'll just say this . . . "Some Ball Yard!"

My comfort level regarding the possibility of my son attending college in Chicago peaked later that evening. While relaxing back at the hotel after a 7-2 Cubs victory over the pitiful Astros, he suggested going downtown again for dinner. What's more, he picked the restaurant (Chinese), mapped out the location and figured out which train we needed to take to get there. The circle was starting to close.

Day Four: Our last day included a visit to Northwestern University, about twelve miles north of Chicago, in Evanston. By this time, Drew had convinced himself that he was going to attend Loyola, and nothing Northwestern could offer would be likely to change his mind. Premature thinking. After two and a half hours and a student-led tour that was - the only word I can think of is - incomparable, Drew was no longer sure of anything except that Illinois would be his future home from 2013 to 2017. As a parent, my thoughts naturally went to his safety. Northwestern is insulated from the city, and campus life would dominate his own. Loyola, on the other hand, offered an education in books but also from the city itself. Thankfully, no decisions needed to be made on Day Four.

Now, comfortably back in Minnesota three days removed from northern Illinois, I am more excited than anxious for my son to attend college, whether it be in Chicago or some other town. So, if for no other reason than that, our brief stay in the "City of the Big Shoulders" was well worth it. But, of course, it was worth so much more . . .

Which makes me wonder - was our trip for his future or my peace of mind? Or both?

Probably both . . . Yes, definitely both.