In southwest Chicago, there is an honest-to-goodness hill that runs through the Dan Ryan Woods down into Beverly. (I've seen another one, too, in Pullman; in this city that's like spotting a rare bird.) Descending it on 87th Street with the woods to the left, if you're able to block out some powerful evidence to the contrary, you can almost think you're coming into town off a mountain, and at the bottom of the hill you'll find a bar where you should stop, apres-ski, for a drink.
This is Reese's Lounge (1827 W. 87th). A note on the door suggests you be at least 30 years old to enter; on a recent visit my crew—28, 29, and, yours truly, 29—spent some time hemming and hawing at the doorstep until the bartender came out told us to get on in already. We were lucky to: with two blue bars on either side of a narrow room, and mirrored walls and blue bar stools and just the right amount of neon, Reese's is embarrassingly comfortable. Beer was cheap; cocktails went unsampled but looked like they would do the trick. In addition to more substantial things like sandwiches, chicken, and fish, the kitchen offers a special diversity of fried foods. We ordered a sampler plate comprising mushrooms, okra, and cheese fries, and there was both mild and hot sauce. We were happy not to have to wait another year or two to hang out here.
Take Reese's, cut it in half, and change the color scheme and you have the J&R Cocktail Lounge (612 E. 79th), in Chatham, with walls that glowed an especially bright crimson during the Valentine's season. Factoring in the color and the coziness, sitting at this bar is like being in some especially big birth canal—a bit more crowded, I suppose. (But to each their own natal experience.) You'll further relax with drinks we adjudged at about two and a half shots per pour—good prices on brand-name liquor, and a very friendly bartender to boot. This is enough to make a fine experience even without the jukebox, which plays the Jackson 5, Prince, and Sade. There's also Ms. Pac-Man.
Arguing over the jukebox was the sport of choice one night at Mr. C's Midway Bar (4654 W. 63rd), located in Clearing, almost literally across the street from the airport. If a place called Mr. C's Midway Bar brings to mind a seamy piano lounge at which sit some louche, miserable businessmen, knocking back one more VSOP before their red-eye flight, I can't argue—it was my vision too, and a little bit my hope—but I must disabuse you. Mr. C's is actually just a really nice neighborhood bar in the style of classic Chicago neighborhood bars that look like they could've been transplanted from a street corner in Green Bay, Wisconsin: wood paneling on the wall, hockey on TV, and signs saying things like "Too Bad Stupidity Isn't Painful." (So true!) A general aviation theme rules the western wall, with old black-and-white photos and aerial shots of the airfield. Mr. C's proximity to its other namesake is hard to ignore; step outside and find yourself, like Wayne and Garth, right underneath the flight path of a descending airplane.
Embrace a travel theme and go north or south. Horse Thief Hollow (10426 S. Western), a capacious family-friendly restaurant with a bar and a barbecue program, opened recently in Beverly. A mixed-'cue plate is pretty good; better still are spicy chicken wings and "spent grain" pretzels, deeply flavorful little bar bits served with a goopy cheese-product-type sauce. When I tried it, Kitchen Sink Pale Ale tasted like it included the dishwater, too, but there are other beers, plus wine and a thoughtful cocktail list.
North, on the other hand, gives you Bernice's Tavern (3238 S. Halsted), a low-ceilinged little Bridgeport hangout that looks like it's been here about a hundred years and has the tchotchkes to prove it: an old CTA fare machine, for instance, and a Wurlitzer, on which the oldies are golden. The crowd itself is a mix of old and young, and there's a house special: "The Special," PBR and a shot of Evan Williams for five bucks.
Another venerable old south-side institution: the Jeffery Pub (7041 S. Jeffery), a gay bar just off the tail end of Lake Shore Drive. We stumbled into the middle of what might've been a birthday party, on a Sunday afternoon, when the place was packed with extremely fancy lesbians with thoughtful hair and excellent dance moves. Patrons drank brightly colored cocktails out of pitchers, and the emcee was bent on getting everybody riled up. Head north or south from here and you'll find a pleasant surprise awaits you: the Jeffery Jump, that rare example of bus efficiency, sits right outside. It's the Dreamliner of public transit, but without the electrical fires.