Christkindlmarket at Daley Plaza: il Porcellino
Once you’ve had your fill of glühwein and holiday shopping, head to il Porcellino for pillowy Whole Loaf Garlic Bread, hearty Italian comfort food like Burrata Lasagna, and 4 kinds of Negronis to warm you up from the inside out.
Make a reservation at il Porcellino
Ice Skating in Millennium Park: Joe’s Seafood, Prime Steak & Stone Crab
After skating under the skyline, glide on over to Joe’s Seafood for a taste of classic holiday tradition—from Oysters on the Half Shell and prime steaks to Alaskan Red King Crab and Florida Stone Crab—paired with irresistible sides like Potatoes Lyonnaise, recently crowned the #1 side at Chicago steakhouses by Chicago Magazine.
Make a reservation at Joe’s Seafood, Prime Steak & Stone Crab
Jack Frost Christmas Pop-Up: The Oakville Grill & Cellar
After you’ve captured all the perfect winter snapshots and enjoyed the frosty fun, pop across the street to The Oakville Grill & Cellar to trade the snow for sun at this California-inspired spot, with craveable signatures like Rigatoni alla Vodka and the Dry-Aged Steak Burger. Top it off with a glass from their curated wine list that will transport you straight to Napa Valley, featuring over two dozen wines by the glass.
Make a reservation at The Oakville Grill & Cellar
Lightscape at Chicago Botanic Garden: L. Woods Tap & Pine Lodge
Your illuminated garden stroll meets peak North Shore comfort at L. Woods, a supper-club–style cabin with French Onion Soup Au Gratin, Baby Back Ribs, Cheeseburgers, Smoked Barbecue Brisket Sandwich, and Pounded Chicken a la Sima, plus a selection of Old Fashioneds with a cozy, Midwestern-holiday vibe. Save room for a Warm Chocolate Chip Cookie Skillet for dessert!
Make a reservation at L. Woods Tap & Pine Lodge
Lincoln Park Zoo Holiday Lights: Mon Ami Gabi
After wandering through the zoo’s technicolor tunnels, slip into the Parisian warmth of Mon Ami Gabi, opening early every Friday until January 4 at 4:00 PM for Holiday Zoo Light Hours. Settle in with Steak Frites Classique, Onion Soup au Gratin, or kid-friendly favorites like Chicken Fingers and Frites. It’s a cozy, festive spot fit for the whole family.
Make a reservation at Mon Ami Gabi
Magnificent Mile Shopping: Tre Dita
A little gift shopping and a stroll beneath the Magnificent Mile’s shimmering lights deserves a meal that feels just as grand, and Tre Dita at the St. Regis Chicago more than delivers. Warm up with their handmade pastas—silky, rich, and crafted with Tuscan flair—and don’t forget to save room for dessert!
Brookfield Zoo Holiday Lights: Wildfire – Oak Brook
After taking in the zoo’s glowing displays, head to Oakbrook Center for a cozy meal at Wildfire. Think classic steakhouse favorites—juicy steaks, tender chops, and seafood—and don’t skip the famous Wildfire Chopped Salad that’ll keep you coming back for seconds.
Make a reservation at Wildfire – Oak Brook
Winterland at Gallagher Way: Ramen-san – Lincoln Park
After wandering the festive stalls and skating on the ice rink at Gallagher Way, fight off the chill with a steaming bowl of ramen at Ramen-san. Their 10-hour Tonkotsu with tender noodles hits the spot, and can’t-miss bites like Pork Belly Mantou Buns or Crab Rangoons make the perfect pre- or post-market treat. Pair it with a cup of Hot Sake for the ultimate cozy reward.
Make a reservation at Ramen-san – Lincoln Park
Winter WonderFest at Navy Pier: Three Dots and a Dash
Continue the winter wonderland fun with a tropical twist at Three Dots and a Dash’s River North Pole pop-up. Sip limited-edition holiday cocktails like Cookies for Santa or Hot Buttered Rum while surrounded by festive décor. A drink (or two) here and you can officially mark off a stop on the Chicago Holiday Cocktail Stroll!
