312 Chicago On December 11, pastry chef Kimberly Schwenke leads a cooking class that teaches how to put a modern twist on classic Christmas desserts. Hotel Allegro, 136 N LaSalle St (312-696-2420). 12–2pm. El: Brown, Pink, Orange, Purple (rush hrs) to Washington/Wells. Bus: 14, 20, 56, 60, 124, 157. Brunch (Sun), lunch (Tue–Fri), dinner. Class: $45 per person.
Ann Sather Ann Sather has the sweetest cinnamon rolls in the Midwest. And since Ann Sather is open every year on Christmas Eve and Christmas Day, there’s no excuse not to gift yourself one. 909 W Belmont Ave (773-348-2378). El: Red to Belmont. Bus: 8, 22, 77. Breakfast, lunch. Average main course: $10.
Artopolis Bakery & Café Greeks exchange gifts on Jan 1, courtesy of St. Basil, who gave his name to vassilopita, a sweet bread into which a coin or other trinket is baked. Whoever gets the slice with the prize is promised good fortune in the next year, so test your luck all holiday season long at this colorful Greektown café. 306 S Halsted St (312-559-9000). El: Blue to UIC/Halsted. Bus: 7, 8, 60, 126, 156, 157. Breakfast, lunch, dinner.Average main course: $7.
Blue Sky Bakery & Café On Dec 11 and 12, pick and choose products from Rare Bird Preserves, Jo Snow Syrups and Pasta Puttana for one-of-a-kind gift baskets. 3720 N Lincoln Ave (773-880-9910).Noon. El: Brown to Addison. Bus: 81, 93. $25–100.
Café Ba-Ba-Reeba! On Tue 30, expect festive crowds at Ba-Ba-Reeba as it holds its Holiday Craft Beer Bodega. More than 30 beers will be offered and paired with tapas, such as cured duck breast over apple toast. 2024 N Halsted St (773-935-5000). 6–8pm. El: Brown, Purple (rush hrs) to Armitage. Bus: 8, 73. Holiday Beer Bodega: $25.
Club Lucky This old-school, family-style Italian joint decks itself out with blinking electronic snowflakes outside, hundreds more snowflakes (and thousands of Christmas lights) inside and special Christmas martinis. 1824 W Wabansia Ave (773-227-2300). El: Blue to Damen. Bus: 50, 56, 72. Lunch (Mon–Sat), brunch (Sun), dinner. Average main course: $16.
Deca Restaurant & Bar The more casual restaurant in the Ritz Carlton celebrates the Ten Days of Christmas (Dec 13–24) with daily specials including complimentary half-dozen oysters with the purchase of a glass of champagne on Tuesdays. 160 E Pearson St (312-573-5160). El: Red to Chicago. Bus: 3, 10, 26, 66, 125, 143, 144, 145, 146, 147, 151. Breakfast, lunch, dinner. Average main course: $19.
Geja’s Café December 1 through February 23 marks the 31st Annual Champagne Festival at what’s considered one of the city’s most romantic restaurants. 340 W Armitage Ave (773-281-9101). Bus: 11, 22, 36, 73, 151, 156. Roederer Estates tasting Dec 5 at 1pm: $30, average fondue dinner: $50.
Joe’s Seafood Just one more excuse to eat sweet-potato-pecan pie: For each carryout pie sold through the end of 2010, Joe’s will donate $1 to the Greater Chicago Food Depository. 60 E Grand Ave (312-379-5637). El: Red to Grand. Bus: 29, 36, 65. Takeaway pies are $29.95, average main course: $30.
M Burger When are burgers and fries appropriate holiday foods? When they’re served with the current secret shake flavor: Peppermint. 161 E Huron St (312-254-8500). El: Red to Chicago. Bus: 3, 66, 151, 157. Average main course: $4.
Mundial Cocina Mestizo A traditional winter dish in the Yucatan (and an annual offering at this Pilsen favorite), chiles en nogada take on extra meaning around Christmas, when the fried poblano pepper—stuffed with seasoned pork and beef and topped with a nut-cream sauce—is said to represent the infant Jesus in swaddling clothes. 1640 W 18th St (312-491-9908). El: Pink to 18th. Bus: 9, 18, 168. Brunch (Sat–Sun), lunch, dinner (closed Mon). Average main course: $21.
Nacional 27 The centerpiece of Nacional’s Cuban holiday dinner is a roast suckling pig marinated in a spicy, citrusy mojo. 325 W Huron St (312-664-2727). El: Brown, Purple (rush hrs) to Chicago. Bus: 11, 22, 66. Dinner (closed Sun). Christmas dinner: $45.
Old Town Social Head here for a holiday feast made up of chef Jared Van Camp’s charcuterie. And when you’re done, take some of those meats home to give as a gift. 455 W North Ave (312-266-2277). El: Brown, Purple (rush hrs) to Sedgwick. Bus: 9, 11, 72. Mon–Fri 5pm–2am; Sat 11am–3am; Sun 11am–midnight. Charcuterie gift set: $40.
Osteria Via Stato On Christmas Eve, chef David DiGregorio presents a traditional Italian Feast of Seven Fishes. 620 N State St (312-642-8450). El: Red to Grand. Bus: 22, 36, 65. Lunch (Sat, Sun), dinner. Average main course: $18.
Prairie Fire Chefs Sarah Stegner and George Bumbaris have dreamt up a conceit for an over-the-top holiday meal: Order Italian truffles through them, they’ll cook you a meal using the Piedmont delicacy, then you take home any extras. 215 N Clinton St (312-382-8300). El: Green, Pink to Clinton. Bus: 38, 56, 125. Brunch (Sat, Sun), lunch (Mon–Fri), dinner. Truffles are $1,200–$2,000; average main course: $20.
Pupuseria y Restaurante Cuscatleco During the holidays, this Albany Park restaurant cranks out Salvadoran–style tamales, a Christmas tradition throughout Latin America. 3125 W Lawrence Ave (773-539-0977). El: Brown to Kedzie. Bus: 81, 82. Lunch, dinner. Average meal: under $10.
Russian Tea Time A classy choice for anybody doing the holiday thing downtown. Skip the wine and order a flight of house-infused vodkas. 77 E Adams St (312-360-0000). El: Brown, Green, Orange, Pink, Purple (rush hrs) to Adams; Red, Blue to Jackson. Bus: 3, 4, 6, 7, 14, 26, 145, 147, 148, 151. Lunch, dinner. Average main course: $20.
Shaw’s Crab House This fishhouse gets decked out for the holidays with poinsettias, wreaths, garland, white lights—and lobsters! 21 E Hubbard St (312-527-2722). El: Red to Grand. Bus: 29, 36, 62, 65. Average main course: $28.
The Signature Room at the 95th Brunch favorites are accompanied by holiday tunes on the piano and, of course, the view at this restaurant’s Sunday buffet. 875 N Michigan Ave (312-787-9596). 10am–2pm. El: Red to Chicago. Bus: 33, 143, 144, 145, 146, 147, 148, 151. $45 (children 4–12: $25).
Sixteen This year, Trump Tower’s opulent restaurant offers an equally opulent six-course Orient Express–themed New Year’s Eve dinner. 401 N Wabash Ave (312-588-8030). El: Red to Grand. Bus: 29, 36, 65. NYE dinner: $225 per person ($325 with wine).
Smak Tak Poland, like many other predominantly Catholic countries, traditionally observes Christmas Eve (Wigilia) with a fish dinner—and so will this homey, hunting lodge–like restaurant on the Northwest Side. 5961 N Elston Ave (773-763-1123). Bus: 56A, Pace 270. Lunch, dinner. Average main course: $10. BYOB.
Sunda Drop off a new toy at Sunda to benefit a Meadowdale Elementary School student, and you’ll receive a $20 gift card to the restaurant. Through Dec 10. 110 W Illinois St (312-644-0500). El: Red to Grand; Brown, Purple (rush hrs) to Merchandise Mart. Bus: 22, 65, 156 Brunch (Sun), lunch (Mon–Fri), dinner. Average main course: $22.
Tre Kronor From the smorgasbord to the Santa Lucia singers with candles on their heads, this Swedish restaurant’s Julbord dinners are as charmingly old-fashioned as yuletime dining in Chicago gets. 258 W Foster Ave (773-267-9888), El: Brown to Kedzie. Bus: 81, 92, 93. Julbord dinner: $49.95, reservations recommended.
The Walnut Room No holiday shopping trip to Macy’s is complete without a meal (or at least a drink) here, the home of “The Great Tree” (that’s a Christmas tree, natch). 111 N State St, seventh floor (312-781-3125). Lunch, dinner. Average main course: $15.
Celebrate the season withholiday tea.
Atwood Café The daily Mad Hatter’s tea should put even the most exhausted shopper back on her feet. Nov 26–Dec 31 from 2–3:30pm. 1 W Washington St (312-368-1900). Tea: $25 (children: $18).
The Art Institute Every weekend between Nov 27 and Dec 19, the AIC hosts carolers for tea (and songs) in the Stock Exchange Trading Room. 111 S Michigan Ave (312-553-9675). 2–4pm. Tea: $25 (children: $12).
Palm Court at The Drake Carolers and decorations adorn this lavish room during the holidays. The Drake Hotel, 140 E Walton Pl (312-932-4619). Holiday Tea begins Fri 26 from 11am– 4:30pm. $33 (children under 12: $18).
Peninsula The Peninsula’s “Fashion Afternoon Teas” feature informal fashion shows. 108 E Superior St (312-573-6685). Nov 26, Dec 3, 4, 10 and 17, at 2:30pm and 4:30pm. Tea: $40, $49 with a glass of Champagne.
Pensiero Enjoy scones and finger sandwiches in the “grand parlor room” at a special holiday tea. 1566 Oak Ave, Evanston (847-475-7779). Fri, Sat and Sun (except Dec 25) through Jan 2 from 1–5pm. Tea: $19.
Seasons Restaurant Children get complimentary tea service here when you bring a toy to donate to Toys for Tots. Four Seasons Hotel, 120 E Delaware Pl (312-649-2349). Tea: $32 (children: $15).
November 25–December 1 | Dec. 2–8 | Dec. 9-15 | Dec. 16-22 | Dec. 23-29 | Dec. 30-New Year's Eve