10. Kick out 2011 in style at EMERALD LOOP BAR & GRILL. Located in the heart of downtown, this New Year's bash includes premium open bar and premium appetizer buffet, party favors and champagne toast. 8pm-1am. $75. 216 N. Wabash. Make reservations at 312/263-0200 or 312/867-7717. 9. Ring in the New Year in style at VERTIGO SKY LOUNGE with incredible rooftop views, signature plush robes, crystallized fire pit and fur blankets. Enjoy premium open bars, live DJ entertainment, passed hors D'oeuvres, late night snacks, and a champagne toast at midnight. Open bar 9pm-1am (party goes until 3am). $105 (price to increase based on availability). 2 W. Erie. 312/202-6060. 8. If it's New Year's Eve in Chicago, veteran rockers Big Head Todd and the Monsters must be playing a party nearby; this year, the balloon drop takes them to the HOUSE OF BLUES. 8pm. $62.50. 329 N. Dearborn. 312/923-2000. 7. Each year, tens of thousands of locals and visitors alike descend upon the lakefront for prime viewing of NAVY PIER'S annual fireworks extravaganzas. Navy Pier offers up a preliminary round of fireworks at 8:15pm, then once the clock strikes midnight, the Pier will again be illuminating the night sky with more fireworks. FREE. 600 E. Grand. 312/595-PIER. 6. Countdown to new resolutions more than 1,000-feet up at The JOHN HANCOCK OBSERVATORY and enjoy the sizzle of Navy Pier's early family-friendly New Year's Eve firework spectacular at 8:15pm and midnight show. Adults $15 (12+), complimentary youth admission with each adult ticket purchased. 875 N. Michigan. 888/875-VIEW. 5. Kick out 2011 at the recently revamped LASALLE POWER CO. The night's festivities include premium bar, hors d'oeuvers, balloon drop, live digital countdown, champagne toast at midnight, and more. 9pm-midnight. $100 ($50 early bird ticket). 500 N. LaSalle. 312/661-1122. 4. Kentucky garage-punk quintet Cage the Elephant brings its live-wire energy to a New Year's Eve bash at the ARAGON BALLROOM. 8pm. $40. 1106 W. Lawrence. 773/561-9500. 3. Ring in the New Year aboard the ODYSSEY, SPIRIT OF CHICAGO, OR MYSTIC BLUE New Year's Eve Fireworks Cruises. Includes food, drinks, dancing and a fireworks display off of Navy Pier. Boarding at 8:30pm. $219.90 for Odyssey, $159.90 for Spirit of Chicago and $147.90 for Mystic Blue. 600 E. Grand. 866/273-2469. 2. Kids in tow? Jump-start your NYE festivities aboard SPIRIT OF CHICAGO. Their New Year’s Eve Family Lunch Cruise features a holiday lunch buffet, DJ entertainment, special countdown to New Year’s Eve at noon, and party favors. Sat, Dec. 31. Boards at 11am, cruises from 11:30am-1:30pm. Adults $47.90, children (age 3-12) $25.95. Departs from Navy Pier, 600 E. Grand.866/273-2469. 1. Spend New Year's Eve laughing with Chicago's hottest interactive improv experience, COMEDYSPORTZ. With suggestions and comments from the audience, the red and blue teams sing, dance, and deliver improved scenes in this no-holds-bar battle of comedy. All shows feature a countdown, party favors, and toast. Check out the early family-friendly shows at 5pm & 7pm. $22. 929 W. Belmont. 773/549-8080.
Start the day’s activities with a trip to Macy’s flagship store (111 N. State; 312/781-1000) on State Street. The eye-catching animated window displays have been a tradition here for 44 years and are a destination in and of themselves for many visitors. On display through January 8, 2012, this year’s widows showcases the story behind “The Wish Factory.” Another centerpiece of Macy’s holiday celebration, The Great Tree rises 45–feet into the rarified air of the world-famous Walnut Room—and is decorated with over 2,000 themed ornaments and 15,000 dazzling LED lights.
That iconic, El-encircled downtown hub otherwise known as “the Loop” provides a classic holiday experience unlike any other. Should the queue at the Walnut Room prove too intimidating, however, there are a number of other nostalgic holiday dining options nearby. For authentic German favorites – not to mention a chance to find the pickle ornament in the Christmas tree (go ahead, ask them) – head over to the venerable Berghoff Restaurant(17 W. Adams; 312/427-3170). Find traditional German dishes and Dortmunder-style beer that made the restaurant famous alongside new contemporary sensations.
A more recent holiday tradition for many Loop visitors has been a trip downtown to see a show in the Downtown Theater District. Among the popular choices, especially at this time of year, are two genuine Chicago holiday landmarks –A Christmas Carol at the Goodman Theatre (312/443-3800) and the Joffrey Ballet’s Nutcracker at the Auditorium Theatre (800/982-2787). Those who prefer a new holiday offering will want to check out Donny and Marie belting out your favorite holiday hits in Christmas in Chicago at the Oriental Theatre (800/775-2000) or follow Ralphie Parker as he makes his journey through the holiday season in search of the gift of his dreams, a Red Ryder BB Gun, in A Christmas Story, The Musical!at The Chicago Theatre (800/745-3000).
Before or after the show, many theatergoers will likely set out in search of a unique gift or a delicious snack at one of the city’s younger holiday traditions like the 16-year-old Christkindlmarket (50 W. Washington; 312/494-2175). This open-air German-style market features over 50 food and craft vendors selling everything from bratwurst to blown-glass ornaments, and provides the perfect setting for Chicago’s magnificent holiday tree at Daley Plaza. Beneath that tree, a line of anxious children is a sure sign you’ve come upon one of the city’s most beloved holiday staples – Santa’s House (312/744-3315).
Last but not least, Chicago Loop Alliance’s 3rd Annual Winter WonderLoop series, which takes place through year’s end, invites Chicagoans and visitors alike to enjoy more than 100 holiday events, traditional festivities, and special discounts at participating stores, restaurants, hotels and cultural institutions. Visit WinterWonderLoop.com for daily specials and holiday offers!
In terms of sheer numbers, the annual December Santa Claus roundup seems to favor the escalators and parking lots of suburban malls. But quantity and quality are two very different things. The success of Claus, after all, relies on authenticity, and you can’t spell “authenticity” without “city.”
Merrymakers visiting Chicago will find more rotund bearded men than they can shake a peppermint stick at during the holiday season. In fact, you can hardly take a break between checking out the holiday windows, shopping for gifts, and grabbing a steaming mug of hot chocolate in this town without finding yourself sitting upon an inviting red velvet lap. Everywhere you turn, it seems, a flying sleigh has deposited its portly pilot onto an elaborate throne, ready to hear Christmas wishes and dole out the cheer.
On the Magnificent Mile, children of all ages will find the big guy perched high above the city streets at the John Hancock Observatory (875 N. Michigan; 888/875-VIEW), and welcoming shoppers at the 900 North Michigan Shops (900 N. Michigan; 312/915-3916) and The Shops at North Bridge (520 N. Michigan; 312/327-2300). Meanwhile, the jolly old elf also covers the downtown “Loop” shopping corridor and Theater District with a post at the Macy’s Santaland (111 N. State; 312/781-1000), along with a prime spot under the city’s official Christmas tree Daley Plaza (50 W. Washington; 312/744-3315). You’ll also find old Kris Kringle greeting the kids outside of Winter Wonderfest on Navy Pier (600 E. Grand; 312/595-PIER) and bringing some joy to the animals during the ZooLights Festival at Lincoln Park Zoo (2001 N. Clark; 312/742- 2000).
From sugar plums to candy canes, nothing symbolizes the sweet, joyous nature of the holiday season quite like a great dessert or snack treat. Whether as a thoughtful token for someone else or a special indulgence for oneself after a day of hectic holiday planning, a little sugary something can be the perfect exclamation point on any Season’s Greetings!Eno Wine Room Can’t decide between a swanky wine bar and a decadent chocolate shop? No need to choose here – create a perfect pairing in this sleek, comfortable environment with the help of a knowledgeable staff and plenty of tasting opportunities. 505 N. Michigan. 312/944-4100 and 200 N. Columbus, 312/946-7000. CandyalityJust how happy is a kid in a candy store? Find out at this colorful bulk candy emporium that makes everyone feel like a kid again. From dozens of flavors of M&Ms, jelly beans and licorice to a wide assortment of retro confections, there’s something here for just about every sweet tooth. 520 N. Michigan. 312/527-1010. Eli’s CheesecakeThere’s a reason why these massively rich slabs of sweet goodness are among the best-selling items every year at the annual Taste of Chicago festival – they are, after all, part of the history of this city. At the company HQ, visitors can take a tour to see how the many flavors get made, then grab a slice in the café and a full pie to take home. 6701 Forest Preserve. 773/736-3417. Magnolia BakeryThe cupcake craze shows few signs of letting up, and this is one of the places that started it all. With dozens of flavors from which to choose – including several made special for the season – this is a perfect place for a quick afternoon pick-me-up or a full dozen to go. Inside Block 37 at 108 N. State. 312/346-7777. The Melting Pot Dip into something chocolatey. Fresh strawberries, cheesecake, Rice Krispies Treats®, marshmallows and brownies accompany delightfully decadent pots of chocolate-fondue including Flaming Turtle, Bananas Foster, and more. 609 N. Dearborn. 312/573-0011. The Fudge Pot They may have changed hands from father to son since opening in 1963, but their delectable fudge recipe has remained the same. Choose from 300 plus molds of old-fashioned chocolate fudge and an amazing assortment of other sweets, including their famous Chocolate Covered Strawberries. 1532 N. Wells. 312/943-1777.