Black Wednesday | Nov 21
Thanksgiving can be a stressful time, what with family members asking about your post-graduation plans and a turkey that needs to be basted every hour—but today the ball is in your court, so to speak. Head to Timothy O’Toole’s downtown Chicago location for their Third Annual Turkey Testicle Festival. The objective should be self-explanatory, and the winner walks away with a free turkey. The event is followed by the bar’s Pumpkin Pie Eating Contest at 11 p.m. and the entire affair is complimented by pool, Jumbo Jenga and very reasonably priced beverages. 622 North Fairbanks Court. Starts at 9 p.m., free.
Thanksgiving | November 22
’Tis the season for news outlets everywhere to tout fantastic new strains of Tofurkey and vegetal Turducken. This time around, though, put your faith in the Chicago Diner’s 30th Annual Vegan Thanksgiving, rather than some sad, shrink-wrapped object from your local grocery store. Entrée options include Veggie Turkey (seasoned tofu roast stuffed with wild rice and topped with country gravy), Pumpkin Ravioli, and Beefy Wellington (the secret is there is no beef, only seitan). 3411 North Halsted Street. Takeout only, orders accepted 9 a.m.–noon, prices vary.
A Thanksgiving filled with southern hospitality is always best—how else will you get that turkey in the fryalator? Andersonville’s Big Jones pays homage to the sizzle and spice of Cajun cookery with a comforting, three-course prefix menu. Appetizer options include Cajun Pork Boudin Fritters and Charleston She-Crab Soup, your entrée can be anything from Wood Grilled Snake River Sturgeon to King Trumpet Mushrooms & Wild Rice Pie, and for dessert, brussels sprouts. Just kidding, they’ve got Bourbon Bread Pudding with Cinnamon Streusel and Coconut Cream Cake, of course. Additional perks include a relish tray and selection of veggies served family-style. 5447 North Clark Street. 11 a.m.–7 p.m; $48 for adults, $20 for children under 12.
If your family is in town, why not serve them their turkey and sweet potatoes with a slice of Chicago’s skyline? Sure, it won’t taste exactly like pumpkin pie, but it might facilitate the taking of an embarrassing group photograph. Odyssey Cruises is offering special Thanksgiving Day trips up and down Lake Michigan. Guests are treated to breathtaking views of the Loop and a buffet chock full of classy holiday dishes like Walnut-Crusted Turkey Breast, Cheddar Cheese Mashed Potatoes, and Strawberry Pecan Salad. Leaves from Navy Pier. Boarding at 1:45 p.m., $49.90 per adult, $29.95 per child (lunch cruise).
Staying in Chicago over break? Here’s your chance to branch out. The Morton Arboretum, just a 45-minute drive from campus, is waiving the cost of admission today so visitors can explore its 16 miles of trails (plus nine miles of paved roads). You can stop by the quaintly named Meadow Lake, and frolic through the wildflowers of the Schulenburg Prairie. Still not enough trees for you? Be sure to check out the arboretum’s Fragrance Garden, Ground Cover Garden, and Hedge Garden as well. It’s unbe-leaf-able! 4100 Lincoln Avenue, Lisle, IL. 7 a.m.–sunset, free.
Give thanks as good as you get at the Kit Kat Lounge and Supper Club where Diva Sunny Dee-Lite will be reigning supreme. At Give and Get Thanksgiving, bring any nonperishable food item to benefit the Vital Bridges Food Drive and you will be rewarded 50 percent off your entire bill, which, if you’re smart, will include a special holiday prefix menu decked out with turkey, mashed potatoes, and a pumpkin martini. 3700 North Halsted Street. 5:30 p.m.–2 a.m., $40 prefix. Reservations strongly suggested; call 773-525-1111.
Black Friday | November 23
It’s sort of sad, really, but with cranberry sauce still sloshing around in our stomachs we’re moving on from turkeys to large, stationary felines. Grab some complimentary hot chocolate and gather around the steps of the Art Institute for its 21st Annual Wreathing of the Lions. While there, sit back and listen to the sounds of the Maxwell Street Klezmer Band, and kids who have genuinely convinced themselves that they are lions. You are also encouraged to head to the Ryan Education Center to decorate your very own wreath, though, if you haven’t already guessed, everyone else there will probably be a small child. 111 South Michigan Avenue. 10 a.m., free.
At Barrio Urban Taqueria you can shop till you drop so long as you save some room for dessert (in your stomach, not on your bill). In an act of extremely delicious holiday goodwill, Barrio Urban Taqueria is offering tres leches, flan Napolitano, or sorbet on the house for those Black Friday consumers who are thrifty enough to bring a copy of their receipts to the restaurant. 714 West Diversey Parkway. 4–11 p.m., average main course $11.