Chicago transforms into a winter wonderland during the holidays, offering festive traditions, dazzling lights, and unforgettable experiences for locals and visitors alike. From sparkling cruises along Lake Michigan to cozy pop-ups and vibrant holiday markets, the city and its surrounding suburbs deliver endless ways to embrace the magic of the season. Whether you’re sipping Glühwein at Christkindlmarket, strolling through illuminated trails, or enjoying gourmet dining with skyline views, these must-see destinations promise to make your holidays bright.
City Cruises
City Cruises, Chicago’s premier year-round provider of unforgettable on-the-water experiences, invites patrons to join one of their Holiday Fireworks Cruises this holiday season. Running on Saturdays throughout the month, these cruises combine gourmet dining, festive cocktails, DJ entertainment, and breathtaking views of Navy Pier’s fireworks. Guests can choose from elevated experiences, including the Holiday Fireworks Premier Dinner Cruise, Premier Plus Dinner Cruise, or Signature Dinner Cruise. Whether gliding along Lake Michigan or the Chicago River, these sailings offer the most dazzling way to celebrate the season with family and friends.
The LaSalle Chicago, Autograph Collection
Back by popular demand, The LaSalle Chicago, Autograph Collection has returned as the official hotel partner of Christkindlmarket Chicago 2025. Just four blocks from Daley Plaza, guests can cozy up in refined comfort and enjoy a special holiday package that includes Glühwein drink vouchers, collectible market mugs, and a luxurious stay in The Loop’s elegant hideaway. With live jazz, festive dining at Grill on 21, and easy access to Chicago’s most beloved holiday tradition, The LaSalle Chicago is a sophisticated home base for a season of sparkle. Visit their website here to learn more.
Randolph Street Market’s Holiday Market December
Randolph Street Market’s Holiday Market December 13+14 Deck the halls with all things vintage as the Randolph Street Market hosts its December Holiday Market at Plumbers Hall in the West Loop on Saturday, December 13 and Sunday, December 14. The two-day shopping event features more than 125 vendors offering an eclectic mix of vintage fashion, antiques, art, home décor, jewelry, and handcrafted holiday gifts. Guests can sip festive cocktails, enjoy live DJ sets, and browse one-of-a-kind treasures from Chicago’s top curators and makers, making it the perfect destination to find something truly special before the holidays. To purchase tickets, shoppers can visit their website.
Sonny Acres Farm
Sonny Acres Farm, 29W310 North Ave., is thrilled to ring in the holiday season with the return of the beloved Big & Bright Trail of Lights Festival, officially reopening Friday, November 21 through Sunday, December 21. The West Chicago family farm will transform into an illuminated seasonal destination featuring an enchanted mile-long walking trail, festive treats, fresh-cut Christmas trees, handmade wreaths and unique holiday experiences for families, couples and groups. Beginning November 21, the farm becomes a complete winter wonderland filled with immersive displays, cozy fire pits, treats and sweets, and special appearances from Santa Claus throughout the season. Tickets to the Big & Bright Trail of Lights are available online via Tixr.
Broken Oar Marina-Bar & Grill’s Arctic Winter Bar
Following another year of smashing success, the Arctic Winter Bar is back with even more festive fun, cozy vibes, and seasonal surprises. Running now through February 1, Broken Oar Marina-Bar & Grill in Port Barrington invites guests to experience its crowd-favorite Arctic Winter Bar – a one-of-a-kind enclosed outdoor bar, lounge, and barn that blends cozy comfort with holiday cheer. This year marks a major milestone for Broken Oar as they celebrate 40 years of unforgettable riverside hospitality, and this Arctic Winter Bar season is the most exciting yet. The pop-up has an ongoing lineup of live music on the Oar Stage every Thursday through Sunday. Other highlights this year include the incorporation of the Broken Barn, a spacious 3,000 sq. ft. heated barn, extended holiday hours through New Year’s Eve, and for the first time, full table reservations. Learn more or reserve your spot today by visiting here.
Hyatt Lodge Oak Brook’s Prancer’s Pub Pop-Up
Hyatt Lodge Oak Brook is transforming into a winter wonderland with a full lineup of festive experiences for guests and locals alike. Returning November 28 through January 1, the beloved Prancer’s Pub Pop-Up will once again dazzle visitors with twinkling décor, an all-new menu by Executive Chef John Borras and a reimagined lineup of holiday cocktails. Guests can also reserve one of the hotel’s new outdoor Alpenglobes, private heated domes overlooking the wooded grounds and lakefrnt, for an intimate seasonal dining experience. Families can join the fun during the hotel’s Deck the Halls event running December 6, 13, and 20 featuring gingerbread cookie decorating, build-your-own cocoa mix and reindeer food stations, a coloring corner, and a Hot Cocoa Bar with both classic and spiked options. The hotel’s signature Santa Suite also returns, transforming a one-bedroom guestroom into a storybook holiday escape complete with festive décor, cozy amenities, and floor-to-ceiling views of the property’s picturesque landscape. In the spirit of the season, Hyatt Lodge is also serving as a Toys for Tots donation hub through December 13, collecting new, unwrapped toys for children in need. For more information, visit the hotel’s website.
Lincolnshire Marriott Resort’s Embers Christmas Grille
The Lincolnshire Marriott Resort concludes its 50th anniversary by offering a one-of-a-kind holiday experience at its signature Three Embers Restaurant, coinciding with the award-winning Marriott Theatre’s milestone season. The resort’s newest pop-up, Embers Christmas Grille, transforms Three Embers into a festive retro holiday lounge, complete with bold visual nods to rock ‘n’ roll legends. Guests can savor a themed menu crafted by the restaurant’s culinary team, designed to transport diners into the world of the stage while enjoying seasonal flavors and creative cocktails.
Marriott Theatre’s Million Dollar Quartet Christmas
Across the hall, the Marriott Theatre presents Million Dollar Quartet Christmas, a high-voltage musical celebration of four legendary voices – Johnny Cash, Jerry Lee Lewis, Carl Perkins, and Elvis Presley – coming together for a holiday jam session at Sun Records. This Tony-nominated hit brings energy, nostalgia, and holiday cheer to every performance. To book your tickets, please click here.
