We packed the car and hit the road in the morning, although not nearly as early as we had originally planned, and by the time we'd stopped for gas and then again to pick up bagels and cream cheese to take with us, it wasn't morning any longer. 
The road to Chicago never really feels like a long one to me. On the way to any vacation I find myself full of excitement and energy. Calvin usually takes a nap, Jon, too, and by the time I'm getting bored, with only the hum of the road to keep me company, we're already catching whiffs of Gary through the car's air intake. From Gary it's no time at all, and everywhere we are surrounded by novel scenery in the form of running down industrial centers, and oftentimes construction work, too. This trip enveloped us in low, gray clouds and a cozy, drizzly rain that seemed to lift just as we were hitting the parking lot that is I94 and 290 going
through the big city.
Part of the impetus for this trip was a desire to see my brother's new digs—a turn-of-the-last-century loft on the edge of the West Loop. I loved it already when I realized that safe street parking was incredibly easy to find, and its tree lined street, beautiful brick walls, wood floors, tall windows, and wide-reaching view just added to that sentiment. On our first day we spent some time walking through the surrounding area, finding enjoyable oddities in architecture, and then picked up the ingredients for a fajita dinner that 
we made back home on Curtis's brand new incredible stove, Calvin in the background jumping up on nearby furniture to look out the window every time he heard the sound of an approaching L on the tracks about four blocks away, to which he nearly always added the exclamation "train" with undying enthusiasm. It's not that the train is that loud or that close, but that the child is that incredibly taken with trains.
Curtis is a great sport. He's been in the big city for nearly two years now, and has absorbed city living in a way that makes him nearly a local in his own right. It's a big city, especially compared to the small big town we were raised in, but he knows the streets, he knows the places to eat, he knows the suburbs. I don't think he's ever lost. 
But he's a great sport because he had absolutely no qualms about playing tourist with us for a weekend. He did not even flinch when, waiting for the L on Saturday morning, we took out our camera and started snapping away. It was, after all, Calvin's first train ride! He loved being near the track, and if he was a little hesitant about the rush and noise of the actual trains themselves, we'd talked a lot about what to expect before we got to the platform and he took the new situation in perfect Calvin stride (meaning, he was quiet and contemplative for the first half of the journey out, but non-stop questions the for its remainder).
The trains were really the highlight of this trip, at least as far as Calvin is concerned. On Saturday we took the green line, 
transferred to the brown line, then again took the brown line, transferred to the green line, and ultimately arrived back where we started, with only a stop in Lincoln Park, a trip to the zoo, and a late lunch to interrupt the fantastic journey. On Sunday we drove to watch Curtis play soccer, but the soccer field lies right at the foot of multiple tracks, and the soccer game was actually more of a side entertainment to the recurrent passing of all manner of trains (the L, the Metra, and even several freights). The view from Curtis's place includes a panorama of the big city, but that was really just a backdrop to the frequent train sightings on the both L and Metra tracks. And, no matter where we were, Calvin heralded the arrival of each and 
every train with that same exclamation of "train" with the same undying enthusiasm.
There was more to the trip. The Licoln Park Zoo was wonderful, and I hope to visit it again when it is both warmer and not actually nap time. Chicago food, like the deep dish pizza we had Saturday night and the true Chicago Dogs we inhaled for lunch on Sunday, punctuate a trip like this with fattening pleasure. On our walk home from the L station on Saturday we stopped at a little local wine shop to quick pick up a bottle for dinner, only to find friendly staff, a free wine tasting, and a 10% discount for locals like Curtis. 
On Sunday, in a last ditch effort to find one more cool thing to do, we ended up at Garfield Park Conservatory, an enjoyably green oasis in the middle of a run down city neighborhood. I guess you could call this the trip of trains, good food, and surprisingly enjoyable finds. When we hit the road to come home at about five on Sunday we knew we'd be driving after dark and after bedtime, but the road back from Chicago never feels very long to me, and always ends in a warm homecoming, padded with the memories of a great trip.
There are a lot of fun pictures, from four different photographers, in the Chicago trip, October 2009 album.