Embrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl around in the frosty air with historic Wrigley Field in the backdrop. Admission to the rink … [Read more...] about Ice skating at Gallagher Way
Holidays
Rudolph’s Rooftop
Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through January 25, 2026. Head to the … [Read more...] about Rudolph’s Rooftop
Skate in the Clouds at Peninsula Sky Rink
Ice skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with sparkling lights and pine trees. The rink is open through February 16, 2026. Ride up to … [Read more...] about Skate in the Clouds at Peninsula Sky Rink
Chicago Artisan Market
Kick off your holiday shopping experience and discover the best in Chicago's handcrafted goods at the Chicago Artisan Market on December 14, 2025, in the West Loop. Shop for one-of-a-kind fashion, food, jewelry, art and home goods at this curated specialty marketplace. This flagship holiday market … [Read more...] about Chicago Artisan Market
Winter WonderFest at Navy Pier
Enjoy all that's jolly and bright during the festive season at the beloved Winter Wonderfest at Navy Pier. Slide, skate, ride and soak up holiday fun at this indoor fest from December 5, 2025, to January 4, 2026. Head to Navy Pier's Festival Hall and take in the 420-foot holiday … [Read more...] about Winter WonderFest at Navy Pier
Maggie Daley Park Skating Ribbon
Whirl around the twirling ice skating ribbon at Maggie Daley Park for the ultimate winter season experience. The Maggie Daley Park Ice Skating Ribbon is open every day from November 14, 2025, through March 8, 2026. Roll around the whimsical ice skating ribbon for a more exciting ride than … [Read more...] about Maggie Daley Park Skating Ribbon
Handmade Market at Empty Bottle
Head to a classic Chicago tradition to supply your shopping for the holidays and beyond at Handmade Market at the Empty Bottle. This month's market opens on December 14, 2024, but the market returns on the second Saturday of the month through April 2025. Handmade Market connects the makers of … [Read more...] about Handmade Market at Empty Bottle
Light up the Lake at Navy Pier
Chicago's largest indoor light experience is a family fun tradition. Light Up The Lake returns to Navy Pier from November 29 to January 5, 2025, for lots of interactive activities. Dive into twinkling holiday magic with Light Up The Lakes light displays, games, visits with Santa and more. This … [Read more...] about Light up the Lake at Navy Pier
McCormick Tribune Ice Rink
Glide under the sparkling beauty of the Chicago skyline at the McCormick Tribune Ice Rink in Millennium Park. The free rink is open from November 15, 2024, through February 2, 2025, weather permitting. Whirling around the McCormick Tribune Ice Rink under the city's official … [Read more...] about McCormick Tribune Ice Rink
Mercado Navideno at Museum of Mexican Art
Add the colors and traditions of Mexico to your holiday shopping with a visit to the Mercado Navideno at the National Museum of Mexican Art on November 29-December 1, 2024. Explore hand-crafted gifts from Mexico including ornaments, nativity scenes, art, jewelry, apparel and toys. You won't have … [Read more...] about Mercado Navideno at Museum of Mexican Art
Book Your Santa Photos in Chicago – Free Photo
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Celebrate the magic of the season with an unforgettable photo experience. With a jolly, authentic Santa and a friendly team that knows how to make families feel at home, you can skip the long lines and stress. The company behind the photos, Cherry Hill Programs, has been taking … [Read more...] about Book Your Santa Photos in Chicago – Free Photo
Halloween House Music Party
Halloween just got more spirited with a special Haunted House Music Halloween Party on October 31, 2024. Chicago's homegrown sound will pump through a night of ferocious beats and non-stop dancing. The legendary Farley Jackmaster Funk and Gene Hunt will spin records featuring some of their … [Read more...] about Halloween House Music Party
