Downtown Chicago, as viewed from the coach yard.
Why go: Chicago is one of North America’s great cities–birthplace of the skyscraper, home to some major museums, and beautiful, walkable neighborhoods. Very easy to get around without a car thanks to a comprehensive subway and bus system. Millennium Park, built on the site of the old, downtown Illinois Central trainyard feature “the bean’ (a two-story-tall, irregularly shaped gazing ball), fountains and gardens. Walk the Magnificent Mile and check out the shops in the Loop downtown.Out in Oak Park, you can tour Frank Lloyd Wright designed buildings. It takes about three days to see all the visitor hotspots.
Private Car parking in CHI: Cars are parked in the coachyard, south of the station. You and your car are in a safe place, and you’re close to the Roosevelt Road entrance ramp, which is a 3-4 block walk to the nearest El station. This is a active railroad yard–you need to be sober, wearing shoes, alert for moving trains, and aware of your surroundings at all times. Cars can get switched at any time, and it’s not unusual to leave a car for a few hours and not be able to find it when you return. Guests and owners are generally welcome (tolerated is probably a better word here), it’s not the safest or most convenient spot for staying on the car.
Chicago highlights for private car folks: If you’re working the trip, there’s a Whole Foods and a Trader Joe’s on Roosevelt that you can walk to, but the nearest Grainger Supply is a short cab ride away on the Lower West Side. If you’re sightseeing, public transit is great–a one day pass is $10 and can be purchased at any subway station. Provisioning highlights–Blommer Chocolates (a large chocolate factory very close to Union Station); and Paulina Market which sells wursts and premium butcher and deli items.
Other transportation: Easy trip to Midway Airport for Southwest and Porter flights. Station is a central Amtrak hub with trains leaving for both coasts every day, and there’s a Hertz car rental counter there.
Anything else: In the last ten years, Chicago has become chock-full of gentrified neighborhoods, wonderful restaurants, and beautiful public spaces– my favorite neighborhood strolls are Paulina and Andersonville, and I’ve spent a few rewarding rainy days at the Newberry Library, and Art Institute. Oh, and the beer: Chicago pioneered craft brewing in the 1990s with Goose Island– local favorite craft beer bars include the Hopleaf, and the Map Room.