What To Do In Chicago During The Holidays
Cities take on a certain magical quality during the holidays. The lights and decorations transform the urban landscape into a glittering space that brings joy to even the Scroogiest of hearts. An air of nostalgia tickles the brain in just the right way so that not even the gloomiest days can ruin the experience. Chicago is no stranger to the magic of the holiday season. While the city is known for soaking up every minute of summer, locals also love to embrace every moment that celebrates this festive time of year.
The “unofficial” kick-off to the holidays in Chicago is the weekend before Thanksgiving with the Magnificent Mile Lights Festival. The Christkindlmarket begins that very weekend, and the official Tree Lighting Ceremony in Millennium Park takes place as well. Macy’s unveils their seasonal decorations, the Chestnut Room’s massive Christmas Tree makes its debut, the ice skating rink below the Bean opens, and the city is alive with an energy you can’t experience anywhere else this time of year. Native Chicagoans have likely experienced these main holiday festivities growing up, but the real spirit of the season lies beyond the central downtown hub and in the neighborhoods.
In between parades and lighting ceremonies, venture around the city to a few of these local favorites:
For the richest, dreamiest, most delicious hot cocoa…
Head to Mindy’s Bakery in Wicker Park for hot chocolate with a marshmallow. The brainchild of Mindy Segal, Mindy’s Bakery is the 2nd concept from the James Beard Award-winning chef. Her first, Mindy’s HotChocolate, was deeply mourned by locals after its closing in 2020. However, that grief didn’t last long when she opened Mindy’s Bakery, which thankfully offers her classic Hot Chocolate with a housemade marshmallow, just like before. Warm up with a cup of the good stuff or one of their other signature drinks like the Hot Chocolate Grand au Lait and a delicious pastry.
We’d be remiss not to mention Cocoa + Co. in Old Town, whose entire personality is chocolate. Try one of many drinking chocolates with a pastry on the side. Bittersweet Pastry, with two locations (Lakeview & Pilsen), has a 30-year-old signature Hot Chocolate recipe that feeds the soul. Finally, Bombobar will forever be one of our favorite spots to grab a treat. Enjoy a simple hot cocoa or get one of their signature hot chocolate drinks. Regardless, don’t leave without trying a bombolini. It’s well worth the sugar rush.
Bombolini from Bombobar
For holiday shopping away from the downtown chaos…
Head to Lincoln Square, specifically the strip of Lincoln Avenue from Lawrence to Leland. This small but mighty area is essentially the “heart” of the Lincoln Square neighborhood, with a Christmas tree in Giddings Plaza, a variety of cafes and restaurants, and lots of small shops. With a vibe similar to Stars Hollow from Gilmore Girls and small towns in every single TV holiday movie, this area of Lincoln Square enthusiastically indulges in the season.
Start by grabbing a warm beverage at Oromo Cafe, a Turkish coffee shop serving traditional Turkish coffee, as well as a full menu of classic and specialty coffee and tea options and dozens of homemade sweet and savory pastries. Pop into Merz Apothecary for a knowledgeable staff who will gladly guide you toward the best self-care items to gift this season. Head across the street to eco-friendly shopping at Planet Access, a store featuring sustainable clothing and accessories where each purchase supports an important mission. The Book Cellar is the perfect neighborhood bookstore with staff recommendations that will keep you browsing for hours. Keep the day going with a stop at Gene’s Sausage Shop & Delicatessen. Grab something for dinner later, or treat yourself to a snack from countries around the world (don’t miss the French and Italian sweets!). They’re also a great spot to grab a gift for a party you’re going to. If you want to dine out, finish the day at Barba Yianni Grecian Tavern for a cozy dinner and a great selection of Greek wines.
Another great neighborhood for holiday shopping is the Southport Corridor, home to both independent businesses and larger mainstream stores like Gap, Sephora, and Anthropologie. Start the day with coffee and a bite from one of several places, including Southport Grocery & Cafe, a local favorite serving breakfast and lunch, Steingold’s of Chicago, a counter-service Jewish deli with delicious bagels, or Bombastic Cafe, a trendy coffee shop featuring single-origin specialty coffee and other beverages like color-changing lemonade.
Dive into your shopping spree, but make sure to check out some of the smaller, independently-owned boutiques while you’re at it. There are several options for clothing, gift shops, and even a candle bar where you can create your own scents. If you get hungry, grab a snack at Cafe Tola – some of the best empanadas around – but save room for dinner at one of many incredible restaurants along Southport. Stephanie Izard’s Little Goat Diner is always a good choice with unique flavor combinations like the Bull’s Eye French Toast + Fried Chicken or Sloppy Chicken Sammie. Crosby’s Kitchen is another solid option with traditional American comfort food. The Mini Filet Sliders and Skirt Steak Frites are hearty options that warm you up on a cold day. For traditional tavern-style pizza, D’Agostino’s is arguably the best in the city. Finally, it would be a tragedy not to mention the star of Southport Corridor – the Music Box Theatre. This landmark shows the classic holiday films It’s a Wonderful Life and White Christmas through December, including sing-a-long screenings. Don’t sleep on tickets because it’s a tradition for many people, and seats go quickly in advance.
The Christmas Tree at Wrigley Field’s Gallagher Way
Enjoy a pop-up or two…
Chicago loves its seasonal pop-ups. Whether it’s the holidays, Halloween, Valentine’s Day, St. Patrick’s Day, or just a great theme that happens to be trending, the city has embraced the idea with open arms. While this statement isn’t fact-checked, it’s safe to assume the holiday season sees the largest concentration of pop-ups at any given time. If you’re looking for a bar crawl vibe where you can hit up as many pop-ups as possible in one night, Clark Street in Wrigleyville has over a dozen along the strip, including Santa Baby Christmas Bar, Elf’d Up, and the Christmas Club. The Nutcracker Pop-Up in the Commons Club at the Virgin Hotel is an over-the-top experience with Instagram-worthy cocktails, treats, and endless photo opportunities. Winter Wonderland at The Godfrey Hotel transforms its terrace into an indoor-outdoor holiday dream with igloos, firepits, delicious cocktails, bites, and more.
If you’re staying central to downtown Chicago…
The easiest way to enjoy what the city offers during the holidays is by simply walking around. Stroll down State Street for iconic views of the Chicago Theater and to see the window displays at Macy’s. Michigan Avenue, south of the River (Lake to Roosevelt), has spectacular views of Millennium and Grant Parks. Michigan Avenue, north of the River, is the famous Mag Mile, beautifully lit up for the season. There are festive trees in multiple locations, including the Wrigley Building plaza and the lower plaza at the Hancock Tower. All three areas have plenty of shopping, dining, and hotels for every budget.
…see a show!
Theater season is in full swing during this time of year. Broadway in Chicago typically hosts at least two or three major touring productions or shows being workshopped. In 2024, you can expect Harry Potter and the Cursed Child, which has been running since October, and & Juliet in the first half of December, followed by Les Miserables. The Joffrey Ballet and Lyric Opera take turns with holiday-themed performances, including The Nutcracker, which runs yearly along with The Goodman Theater’s production of A Christmas Carol. Second City, the famous comedy troupe, additionally puts on a holiday production for a laugh-filled evening. Many of the annual productions and screenings (like the previously mentioned films at the Music Box) are traditions for local families in the general Chicagoland area, which means tickets sell out. If you’re visiting and interested in any of these shows, purchase tickets sooner rather than later. It’s also wise to keep an eye out for holiday shows. Many artists and musicians with holiday tours will stop in Chicago, frequently performing at The Chicago Theater, Chicago Symphony Orchestra, and other mid-sized venues. Past performers include Idina Menzel, Mariah Carey, Michael Bublé, and Harry Connick Jr.
