Cloud Gate, a.k.a. the Bean (via Wikimedia Commons)
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!)
The Kenyon Thrill 
I too am not from Chicago, but these are the lists I use when making restaurant decisions there. I have to put in a plug for Hot Dougs (http://www.hotdougs.com), which is totally overrun by food-obsessed tourists like myself but doesn’t seem to be worse off because of that.
http://petersagal.com/2011/09/my-chicago-restaurant-list/
http://www.lottieanddoof.com/chicagoguide/
When it comes to Chicago style pizza go to Gino’s East. Uno’s taste pretty similar to the Uno’s you can get frozen at the grocery store (aka sub par) but Gino’s East is to die for PLUS you can write on the walls to commemorate your trip, in fact it’s encouraged if you can find an open spot. *I am from the Chicago area and will fight other Chicagoans over these claims
DRINK: CHOCOLATE CAKE MILKSHAKE FROM PORTILLO’S HOT DOGS. ORGASM.
(puts on pizzabox boxing gloves) I agree that Uno’s is crap, and Gino’s is okay, but Lou Malnati’s is the best in terms of real Chicago deep dish. You can’t argue with their almost frightfully sweet and sumptuous tomato sauce.
Also dude with Portillo’s, they sell you who chocolate cakes through the drivethrough window, ’nuff said.
Okay yeah Lou Malnati’s is pretty good. I guess I just write it off because I can get it delivered whenever. However, because I lived in the suburbs Gino’s East is something that I only get while in the city.
I can guarantee that both anonymous posters above are from the suburbs. Real city folk tend to order from Gino’s East. Lou Malnati’s is always full of Cubs fans from Schaumburg.
Other great attractions:
-Second City: I would argue the best improv theater company in the country, has produced dozens of SNL actors and started the careers of people such as Chris Farley and Tina Fey
-Magnificent Mile: Michigan Ave, shopping, great food
-Museum Campus: The Field Museum, Shedd Aquarium and Adler Planetarium all within walking distance of each other
go to wesley’s on 129th and lakeview
Gino’s East is the place to go if you like deep-dish, and Second City is always fun. I’d stay away from the Magnificent Mile, it’s expensive and not as grand as it used to be. Definitely spend all day at the Art Institute. The entrance fee can make you think twice, but it’s amazing (and the new Modern Art wing is awesome!). If you can’t make it there, the Field Museum and Museum of Science and Industry are great bets as well. If you’re looking for a used bookstore, head over to Myopic Books off the Blue Line (Damen exit). Their selection is brilliant. Also, Lincoln Park Zoo isn’t that bad, plus, it’s free and near the Lake, so you can really feel the cold up close.
(And yes, I’m from a suburb of Chicago and go into the city quite a bit. These are definitely some of the big tourist picks and a good way to start a first time visit.)
For the Michelle Obama Style-obsessed, head over to Ikram (15 E. Huron, Gold Coast area), which is one of her favorites. BEYOND expensive- yes, but the clothes and the store itself are such a treat to browse and walk through! For more Chicago shopping, be sure to check out Refinery29 (http://www.refinery29.com/chicago/store-guides). I find their city recs to be spot on!
CFDA (Council of Fashion Designers of America- if you have not seen The Fashion Fund on Hulu, watch it over Reading Days!) runners-up, Creatures of the Wind, are based in Chicago, where Shane Gabier works as a professor at SAIC. I would totes try to sit in on one of his classes…but that’s just me!
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