Just because you're in a strange city doesn't mean you should be forced to wile away the evenings in your hotel bar. Even if you didn't spend weeks doing research on obscure cocktail joints before your travels, you still deserve a good drink. And while Chicago has plenty of great bars in out-of-the-way neighborhoods, you can get a darn good cocktail right in the middle of tourist-town.
Here are some of the best drinking destinations near major tourist attractions in Chicago. Some are full-on craft cocktail bars, while others might be slightly less obvious spots, like restaurants with great cocktail programs and a cozy spot to sit.
Museum Campus: Acadia
The Museum Campus is a bit of a hike from any major business area, and the South Loop hasn't gotten a really good bar yet. However, the neighborhood has one trump card—Michelin-starred Acadia. In addition to artfully plated tasting menus, Acadia boasts a substantial bar with its own menu of creative cocktails (all $13). Try the Maine Campfire, a smoky concoction made with Los Nahuales mezcal, High West rye, tobacco, cedar and juniper, or sip on barman Arunas Bruzas' newest addition to the menu, the Hotter Toddy. A twist on the traditional toddy, this is made with Filibuster bourbon, cider spice tea and honey and comes with a Scotch lollipop and a fiery float of overproof vodka.
Art Institute and The Loop: Tesori, Henri
Don't be intimidated by the posh surroundings at Henri, the tiny jewel box of a restaurant just steps from the Art Institute of Chicago. The food may be a bit pricey, but the bar is open to all comers. Sip on a signature Burnham Manhattan (named for architect Daniel Burnham who designed the building Henri is in) or go for a more adventurous Puritanical Ban, made with hot Flor de Cana 7-year rum, St. Elizabeth allspice dram, and gingerbread rooibos tea from Rare Tea Cellar. (All drinks $13)
If you're looking for more of an upscale happy hour vibe, head to Tesori, an Italian restaurant right next to the Symphony Center. While it gets pretty packed before concerts (and most diners are concerned with getting in and out fast), it boasts a huge, beautiful bar. The cocktail program (drinks $12-$16) has recently been revised by mixologist Tyler Lymer, and it's full of classics, some standard and some more obscure. Try a Vesper made with Carpano Bianco (Lymer is the first person in Chicago to stock it) or a Mary Pickford made with Brugal Extra Dry rum, Luxardo maraschino, pineapple, and grenadine. If you're brave, shots of Fernet Branca are on tap for just a dollar.
Michigan Avenue Shopping: Sable, Three Dots and a Dash
Chicago's cocktail geeks are pretty much unanimous on one thing: the best drinks in River North can be found at Sable Kitchen and Bar, the restaurant in the Palomar Hotel. Curated by mixer Mike Ryan, the drink list here is extensive. Don't let them give you the short menu—demand the full book of cocktails (all $13-16), which runs more than 10 pages and includes modern drinks and a wide selection of classics. Sable just revamped its drink list with a focus on whiskey cocktails for winter (Ryan released a whiskey "manifesto" for the new menu a few days ago), but this is one of the few bars in the city where you could close your eyes and point at the menu and be guaranteed something wonderful.
Three Dots and a Dash has been teaching visitors the true meaning of Tiki since it opened this summer. What better way to recover from a long day of shopping (especially if you're experiencing a signature Chicago sleet-storm) than by pretending you're in a tropical paradise for a few hours?
You can't go wrong with a classic Mai Tai, made with aged Rhum Agricole, Jamaican Rum (mixer Paul McGee won't disclose what kind), lime juice, curaçao, orgeat syrup, and mint. If you're not a run fan, try the Tall as a Tree and Twice as Shady, made with Scotch, Batavia Arrack, lemon and pineapple. You can even bring home a souvenir—their custom tiki mugs are all for sale. On second thought, maybe skip the shopping and just go straight here. (All cocktails $13)
Willis Tower: CH Distillery, Vera
CH Distillery is Chicago's only bar-distillery, and as such, it's a tourist attraction in itself. If you sit at the bar, you can see all of their stills, mash tanks and bottling equipment, and the cocktails (all $11) are made with liquor distilled on the premises. Our favorite drink? The Cease and Desist (formerly known as the Oxycontin, before a lawsuit threat) made with CH Distillery London Dry gin infused with lapsang souchong tea, ginger, honey syrup, and lemon juice. You can also buy bottles of gin and vodka to take home with you.
Vera is known for its Spanish bites and an incredible sherry selection, but many don't realize it also has a great cocktail menu. It's a warm, cozy space with a small bar, and if you have a friend who is a wine lover, Vera is the perfect place to split the difference. Be sure to try the Solera's Whip, which combines Whippersnapper Whiskey, oloroso sherry, and cava. (Cocktails $7-12)
Lincoln Park Zoo and the Peggy Notebaert Nature Museum: North Pond, Barrelhouse Flat
Steps from Lincoln Park Zoo, North Pond has one of the most overlooked cocktail menus in the city. It's a fine dining restaurant, and most of the focus is on wine, but if you sit at the tiny arts-and-craft style bar in the front, they've got a wonderful collection of spirits and a short but perfect cocktail menu (all $13). The most innovative drink on the list is the Gin, Red Pepper, made with red pepper and rosemary juice, Letherbee Autumnal Gin, cider, and lemon. They're also offering a selection of cheeses and charcuterie in the bar, if you're not quite ready to pay for a full meal. If you're a real fan of Lillet Blanc, they're barrel-aging their own (it's Chef Bruce Sherman's favorite drink) and it's available for $8 a glass.
Barrelhouse Flat's encyclopedic cocktail list has been delighting drinkers ever since the bar opened. You'll be tempted to steal the book, as it's more comprehensive than any cocktail guide we've ever seen. If you want to watch the mixers, head to the bar, but if you want a cozy spot to hang out, go upstairs, order some delicious popcorn and sink into a deep chair. (Cocktails $8-12)