As 5 o’clock nears, the crowd in Daley Plaza grows as thick as a North Woods forest. Vendors at the open-air Christkindlmarket tout their wares—Polish pottery, hand-knitted parkas, soaps made with honey—to their captive audience on this night before Thanksgiving. Chicago’s annual Christmas tree lighting is just minutes away, and until then, anyone who was strolling among the dozens of vendors basically gets stuck. TV trucks prep for live shots. A helicopter hovers, its chop drowned out by the crowd’s chatter. Claustrophobia sets in, and I can’t help but think, Why did I want to come here for Thanksgiving?
Then, across the street, the clock on the 568-foot Chicago Temple tolls.
One. Two. The crowd hushes. Three. Four. Hundreds of cell phones reach above the throng, trained on the darkened 55-foot Colorado spruce. Five.
Mayor Rahm Emanuel flips a switch, lighting the vertical strands of red, white and green lights. Cheers roll through the Loop like a summer wave on nearby Lake Michigan. Eventually, I can move as people funnel through the streets in search of dinner.
I love cooking a Thanksgiving spread. But for the first time, my husband, son and I met my mom, who lives near Cincinnati, for a holiday weekend in Chicago. We snagged a $34 round-trip fare for Mom on Megabus and settled into a two-bed, two-bath River North condo, where we can pad around in our jammies and watch football like we would at home in Iowa. (Except our house isn’t perched 20 floors above the Chicago River.)
On Thanksgiving Day, a bitter wind whips down State Street just in time for the start of the parade. No matter how many times we’ve watched this parade on TV, nothing prepares us for seeing a roughly 50-foot-tall pilgrimized Garfield balloon muscle its way between skyscrapers. Bundled-up crowds clap and wave at the multicultural mishmash: marching bands playing Lady Gaga tunes, dancers moving in Bollywood style, girls doing an Irish jig. I inhale the scent of evergreens laying in the raised beds along State Street, and as Santa wraps up the procession, I realize it’s time for an early dinner.
We walk three blocks to the Palmer House Hilton, where we have reservations at Lockwood (it books up a month in advance) for our first time eating out on this special day. Any worries about it feeling weird melt away when we walk into Chicago’s oldest hotel. Poinsettias, lit trees and waiters carrying trays of mimosas fill the lobby with warm hospitality, while chefs cook more than 120 turkeys and present lavish dessert buffets. Patrons linger over creamy butternut squash soup, turkey, dressing and sweet potato soufflé. All of it tastes better than anything I’ve made myself.
Drowsiness sets in as we continue our Thanksgiving football-watching tradition, laying around in the condo until darkness falls. Then we bundle up and walk the 11 blocks to the Magnificent Mile. White lights ring the trees along Pearson Street, where patrons holding cups of hot cocoa spill out of Ghiradelli and climb into carriages for rides through the tony Gold Coast. As the horses wind past Chicago’s old limestone water tower, the simple clip-clop of hooves gives the neighborhood’s trendy boutiques a historic veneer.
The next morning, we watch as workers climb scaffolding to hang bushy evergreen wreaths around the lions guarding the Art Institute of Chicago. Hundreds of art lovers pack the sidewalk, cameras in hand, to snap the moment, while a gospel choir sings praise on the front steps. Created for the 1893 Columbian Exposition, the bronze lions stand outside of the South Michigan Avenue entrance. We funnel inside and make our way to the Art Institute’s Ryan Education Center, where families already have settled at tables to make art inspired by the amazing collection.
Mike and Lisa Shydlowski bring their three children to the Wreathing of the Lions every year, carrying on a tradition that started when Mike was a kid and his family decorated their replica lion bookends with wreaths. Today, alongside us, they make tissue paper wreaths patterned after Marc Chagall’s cerulean stained-glass windows and talk about their plans to see the Zoo Lights in Lincoln Park and go ice-skating in Millennium Park. “I didn’t have any of these things growing up in a small town,” Lisa says. “I like getting our kids excited for what they have here. The city has so much to offer.”
We find a counterbalance to the zoo’s energy on Friday night at Cloud Gate, the bean-shape sculpture in Millennium Park. Luminarias in paper bags outline a “stage” in front of the Bean where a choir stands. Nearly 1,000 visitors grow quiet as the conductor raises his baton. It takes only a few bars of a simple carol written in an Austrian church nearly 200 years ago to create a sense of peace over the throng. We sing “Silent Night,” and our memories of holidays past blend with the ones we’re making right now.
Top holiday stops
Whether you’re in Chicago for the day or the weekend, these destinations shine at Christmastime.
American Girl Place Yes, it’s a madhouse on Black Friday and beyond. But the store, cafe and Celebration Screen draw generations of girls and women together at Water Tower Place. shopwatertower.com 
Chicago Symphony Orchestra The CSO's Merry Merry Chicago with the Von Trapp's debuts one week before Christmas day and features the great-grandchildren of the original Von Trapp family. cso.org 
Christkindlmarket Dozens of vendors create an open-air community of shopping on Daley Plaza, from mid-November through Christmas Eve. christkindlmarket.com 
Holy Name Cathedral Anyone who has admired grand churches in Europe will see stunning similarities in this River North Roman Catholic church. holynamecathedral.org 
360° CHICAGO Take in four-state views from the 96th floor of this Mag Mile icon (formerly the John Hancock Observatory); the holiday model train display delights kids and trainiacs. 3 60chicago.com 
Lincoln Park Zoo More than 1,000 animals live at this free attraction on the North Side, and the 1 million Zoo Lights brighten an already stellar spot. lpzoo.org 
Millennium Park Free caroling takes place at 6 p.m. on Friday nights during the season. Though crowded, the ice-skating is free, too. millenniumpark.org 
Museum of Science and Industry The annual Christmas Around the World showcases holiday cultures. msichicago.org 
Walnut Room You can’t make reservations, but the wait for a table at dinnertime is shorter than at lunchtime at Macy’s on State Street. Ask for a table under the restaurant’s enormous tree, and order the chicken potpie. visitmacyschicago.com 
For more information: Choose Chicago, (312) 567-8500; choosechicago.com 
What to do
The Art Institute of Chicago The nation’s second-largest art museum parties the day after Thanksgiving during the annual Wreathing of the Lions. (312) 443-3600; artinstituteofchicago.org 
Chicago Children’s Museum Creative play spaces, including a Snow Much Fun exhibit, entertain young kids at Navy Pier. (312) 527-1000; chicagochildrensmuseum.org 
McDonald’s Thanksgiving Parade The annual jaunt down State Street runs from Congress Parkway to Randolph Street; park in the garage at Wabash and Randolph. (312) 239-0457; chicagofestivals.org 
Where to eat
Farmhouse Tavern New in 2011, the hole-in-the-wall River North spot celebrates Midwest beer, farms and flavors, dotting its menu with Wisconsin cheese curds, a winter salad and a chocolate brownie dessert that takes Michigan’s U.P.’s meat and potato concept to new heights. farmhousechicago.com 
The Gage Just north of the Art Institute, the gastropub balances a casual, friendly atmosphere with thoughtful dishes and excellent service. The menu changes every eight weeks or so, but our grilled Buffalo chicken sandwich, burger and creamy pumpkin bisque were outstanding. thegagechicago.com 
Lockwood Inside the Palmer House Hilton, Lockwood’s premier chefs cook up a Thanksgiving feast that is scrumptious and stress-free. lockwoodrestaurant.com 
Portillo’s Christmas decorations and cool Chicago sports memorabilia deck the storied hot dog spot in River North. It also serves killer Italian beef. portillos.com 
Where to stay
Condo rentals For an alternative to hotels, consider a condo rental. The pros: You get more space than a hotel room and save money on meals, and some offer parking. The cons: Property owners don’t always get back to you during your search, and you have to pay for your stay up front. But over a holiday and for families, it’s a welcome alternative. homeaway.com ; vrbo.com 
Chicago River Hotel A freshly styled boutique hotel along the river puts guests within easy walking distance of holiday fun. chicagoriverhotel.com 
Inn of Chicago North of the river in Streeterville, this simple but classy lodging in a landmark building has a small lobby and elevators, but well-appointed rooms and a beautiful rooftop patio. innofchicago.com 
(A version of this story appeared in Midwest Living® November/December 2012.)