The madhouse on Madison, aka the house that Jordan built, aka one of the largest NBA/NHL stadiums in existence but a place that's almost always sold out and filled with rabid Chicago sports fans. The UC is also the best venue (acoustically and sight-lines wise) to see a big-ticket music performance as well.
It's a big box liquor store in Kentucky, where there aren't any sin taxes levied on alcohol. 'nuff said.
Myopic is an awesome book store and a Wicker Park landmark. I love stopping in every time I'm in the ever-changing Wicker Park neighborhood, since it's got such an extensive collection and is such a cool place for hanging out and checking out their books.
The French Market has a pretty extensive collection of food items as well as places to grab lunch, but it's main value is its accessibility since it's part of the Metra Station. The market's a good place to kill some time and pick up dinner supplies while waiting on a train or to meet up with friends for lunch.
I don't even know where to start with Dan's. This place is incredible. By far the diviest bar I've ever been to, but also one of the most enjoyable. You'd almost miss Dan's with its unimposing front tucked in between Adams Morgan's trendier bars, clubs, and restaurants, but once you get inside you're transported at least a handful of decades into the past. The place is cash only and the wall behind the bartender is full of mini bottles of alcohol. When you order a drink (say, a jack and coke), the bartender fills one of those condiment dispensers like 75-80% full of alcohol and tops the rest off with the mixer. If you want an amazing night that you might just forget, definitely go to Dan's.
There are a lot of awesome bars in DC, but The Big Hunt is one of my favorites. Unlike the rest of Dupont Circle that's changing so rapidly that a lot of the places are losing their character, The Big Hunt still feels genuine while remaining accessible. Check out their wing and beer daily specials, and you've got to dig their cabaret nights if you get the chance.
Awesome bookstore right off the Dupont Circle stop, and what makes it even better is that they have a full bar most days of the week. Very cool place to stop in and hang out with a friend on a weekday night!
Definitely one of my favorite bars in the Adams Morgan neighborhood, if not all of DC. Madam's Organ almost always has really solid live music (although you do have to pay a cover on nights when there's music), and they have three floors so you can do everything from hang out listening to the band to chilling on their rooftop deck or playing pool.
Ben's Chili Bowl has been a DC landmark in the U Street neighborhood since long before President Obama stopped by and brought it even more exposure. You usually have to wait in line for about 20 minutes to order, but trust me it's worth it. Great for late night munchies, Ben's is a must for anybody who wants to get a genuine feel for DC.
Big Star, how I miss you. This place is always ridiculously crowded so be prepared to either show up early or else wait in line (not fun in the dead of January), but it's so worth it. The tacos are both adventurous and delicious (for the less foodie-inclined, get the taco that comes in a Fritos bag), and their margaritas are heavenly. The bartenders are a holdover from Wicker Park's initial stages of gentrification (hipster, but friendly considering how packed it gets), and the clientele definitely skews towards yuppy, but oh my god just writing this review is making me miss Chicago and its incredible places like Big Star.