For those of you tired of pretending going to Columbus counts as a real getaway, here’s a trip that’s a little more advanced. If you’ve got a road trip buddy and can shell out for about 400 miles’ worth of gas each way, Chicago is less than seven hours away! And you’ll be richly rewarded by one of the most modern, beautiful, and dynamic of American cities. Chicago isn’t all dirty politics and massive fires and slaughterhouses anymore — this is a city with charm and class. There’s plenty to do to keep you occupied for way more than three days, but after the jump are a few suggestions to get you started.
Navy Pier: This is Chicago’s biggest tourist attraction, but what better way to spend a crisp October day than out along Lake Michigan, enjoying a Ferris wheel and some carnival food?
The Art Institute of Chicago: This is the nation’s second biggest art museum after the Met in New York. Right now, you can catch a major exhibition on architecture, and you can see the original of a painting you’ve seen parodied a million times.
Millennium Park: Completed in 2004, just a few years behind schedule as you can tell by the name, this park is now Chicago’s second most popular attraction after Navy Pier. You’ll find a pavilion for concerts, fountains, large expanses of lawn, and the Cloud Gate sculpture, pictured above. It’s officially (not officially) the shiniest and smoothest object in the world, and you should just go stare at it for a while.
Eat: At Pizzeria Uno. This is one of the best known of Chicago’s famous deep-dish pizza restaurants, and as such, it’s probably going be crowded. Be prepared for a wait, or just hunt around for another place…Uno’s probably too mainstream, anyway. (Uno’s sister restaurant Pizzeria Due is also nearby.)
Stay: At Hosteling International Chicago. Don’t even think about a hotel if you want to stay anywhere near downtown at a reasonable price. HI Chicago is a clean and modern hostel, not one of those fly-by-night European ones where you’re probably going to get murdered. And the location can’t be beat: right in the Loop and close to the El. (Alternate: Work those connections and sleep on someone’s couch. Alternate alternate: Sleep in your car, but there are probably some neighborhoods where this is a bad idea. Tip: park outside the Obamas’ house so you have the Secret Service to protect you/have you arrested.)
(Disclaimer: I’m not actually from Chicago, so take my advice with a grain of salt. But you can meet me there this weekend and we’ll figure the city out together!)