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What to Eat and Drink in Chicago This Week

A Bears game, bourbon, and pumpkin spice truffles make for a very autumnal edition of your weekly dining itinerary.

Truffles at Katherine Anne Confections   Photo: Courtesy Katherine Anne Confections

Monday, September 22

Chili out before the Bears play the Jets tonight at a cook-off and pre-game tailgate at Lottie’s Pub (1925 W. Cortland Ave., Bucktown, 773-489-0738). Guests will get free samples of amateur chili creations and get to vote on their favorites before kickoff (as well as nab stadium cups of Miller and Coors beer for $4).

Tuesday, September 23

In honor of its one-year anniversary, CH Distillery (564 W. Randolph St., West Loop, 312-707-8780) is bringing back its most controversial cocktail for one night only. The Oxycontin cocktail (a mix of CH’s London Dry gin steeped in Lapsang Suchong tea and combined with ginger syrup, honey, and lemon) appeared on the bar’s menu until the drug manufacturer served the bar with a cease-and-desist letter. They winkingly renamed the drink the Cease and Desist, but they’re bringing back the copyright-infringing name for the night—and everyone who orders one of the $11 drinks will get served with a cease-and-desist letter of their own.

Thursday, September 25

Get your pumpkin fix in an acceptably artisanal format at a fall-flavor preview party at Katherine Anne Confections (2745 W. Armitage Ave., Logan Square), where for $25 you can get tastes of all the chocolatier’s autumnal treats—including four kinds of pumpkin-flavored truffles, several spiced caramels, and chai-infused marshmallows. Reserve your spot at the open house, running from 5:30 until 8:30 p.m., here.

Friday, September 26

It’s a month that ends in ‘r,’ which means it’s finally oyster season—and time for Shaw’s Crab House to throw their Oyster Fest Block Party (560 W. Grand Ave., River North). Twenty-five bucks will get you in to the party, though you’re on your own to purchase East Coast and West Coast bivalves to slurp while listening to live music. Pick up tickets here.

Sunday, September 28

Learn everything you’ve ever wanted to know about bourbon while also drinking bourbon at Fountainhead’s (1970 W. Montrose Ave., North Center, 773-697-8204) brunch with historian Michael Veach. He’ll walk through the liquor’s stories and myths over a family-style meal with appropriate drink pairings (such as an heirloom tomato panzanella with chevre and a fried egg alongside a fig-infused Few bourbon), and the whole thing will be followed by a rooftop roundtable discussion. Snag a $40 ticket here.


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