First, begin in daylight. Yes, the sun is the outdoor imbiber’s best frenemy, both the reason to be outside (the warmth!) and the reason to retreat indoors (the sunburn!). But here the courtyard is covered, keeping the unwanted elements (skin-scorching sun, hungry pigeons) out and the best aspects (cool breezes) in. Stake a claim at the communal table, but stay only for a cocktail and some oysters—there are other places to hit, and you need to pace yourself. 161 N Jefferson St (312-669-9900).
You stayed for an extra round of drinks and oysters, didn’t you? That’s okay: The seven-block walk to this palace of pork should work up your hunger again. Here, glass windows open onto the sidewalk patio, creating a seamless connection between the dining room and the street. Sure, being lakeside may be a little nicer than Lake Street–side. But dusk lends a certain charm to this grimy district—especially if your view includes a pile of frites and a couple of tall beers. 837 W Fulton Market (312-733-9555).
Now is the time—and this neo-Indian spot is the place—for a proper meal. Two reasons for this: The sidewalk patio, rife with canvas umbrellas and planters lush with sage and marigolds, seats only 16 people. So lingering with nothing but a drink would be rude. Which leads us to the second reason you need to eat here: The summery cocktails—Indian sangria with cumin and mango or “maharitas” with ginger and cumin—come in pitcher form. If you want to be able to stand after that pitcher is gone, though, you’re going to need a few cumin-rubbed steak kebabs in your stomach. 844 W Randolph St (312-491-0844).
Work off some of that paratha by fighting the crowds at White Sox manager Kenny Williams’s sports megabar. It only opened May 1, which means it will be crawling with scenesters, Sox fans and—well, you. Why are you here when the place is such a madhouse? Because Market is big enough to handle it. No less than three outdoor spaces beckon: a sidewalk café; an enormous, tree-enclosed beer garden; and the coup de grâce, a rooftop lounge. With views of downtown, loungey wicker chairs and luxe cabanas, the rooftop is surely the spot’s most coveted area—so you’ll need sharp elbows to cut through the crowd and grab a seat. 1113 W Randolph St (312-929-4787).
And so it comes to this—a beer to close the night. After all the drinking you’ve done, the wisest beer choice would be root beer. But that’s not going to work here. The beer list—oodles of bottles, plus a lineup of 16 microbrews and Belgians on tap—is too comprehensive for you to order just one. Nursing them on this bar’s rooftop, you’ll see a sparkling skyline in the not-far-off distance. Under normal circumstances, it would beckon to you for further cavorting. But not now. This is where the West Loop ends. And so, too, does your night. 1375 W Lake St (312-666-6775).