Why Winter's Better In Chicago: Beat The Blues With These Local Picks

Winter may be here, but the fun doesn’t slow down in Chicago. From family outings to seasonal events and easy day trips, there’s plenty around town to keep your calendar full. Just remember to double-check hours, weather updates and ticket details before heading out. And if you want even more local winter ideas, keep scrolling — you’ll find a way to get personalized suggestions based on what you love to do.

McCormick Tribune Ice Rink – Outdoor Ice Skating

Address: 1 N Michigan Avenue, Chicago, IL 60602
Phone: (312) 742-5222
Details: Ice skating is back at Millennium Park daily through February 1, 2026 (weather permitting), from 11 a.m. to 10:30 p.m., offering skating sessions beneath the city skyline and near seasonal holiday attractions. Bring your own skates for free during select sessions, or rent onsite. Sessions are released two weeks in advance. Visit the website to reserve tickets online.

Hot Tub Boat – Winter River Cruise Experience

Address: 300 North State Street, STE EE, Chicago, IL 60654
Phone: (312) 644-6411
Details: Bundle up and soak in a heated hot tub boat while cruising the Chicago River on a one-of-a-kind winter adventure designed for groups of up to six passengers. Each private 90-minute cruise offers a warm, relaxing way to take in city views, even in cold weather. Visit the website to view pricing and reserve your cruise.

Museum Of Illusions Chicago – Interactive Exhibits & Optical Illusions

Address: 25 E. Washington Street, Chicago, IL 60602
Phone: (312) 722-6780
Details: Step into a one-of-a-kind indoor experience where more than 60 interactive exhibits, holograms and immersive rooms challenge how you see the world and trick the mind. Located in the heart of Chicago, the Museum of Illusions offers a fun, educational outing for all ages — perfect for a warm winter escape. Visit the website to purchase tickets online.

Gwen’s Winter Curl & Chill – Rooftop Curling & Seasonal Cocktails

Address: 521 North Rush Street, Chicago, IL, 60611
Phone: (312) 645-1500
Details: Head to The Gwen for a festive winter rooftop experience featuring outdoor curling paired with cozy firepit seating. Curling reservations include one hour on the court, a firepit table and a featured seasonal treat, with boozy hot chocolate, mulled wine and handcrafted cocktails available. Visit the website to explore the menu and book your spot.

McFetridge Sports Center – Indoor Ice Skating, Pickleball, Dance Classes & More

Address: 3843 N California Avenue, Chicago, IL 60618
Phone: (773) 478-2609
Details: Home to Chicago Park District’s premier indoor ice rink, McFetridge Sports Center offers year-round ice skating and hockey alongside indoor tennis courts, fitness and wellness programs, dance studios and more. Open daily from 6 a.m. to midnight, the fully accessible facility stays busy with youth programs, recreational activities and special events for all ages. Visit the website for schedules and program details.

Chicago Botanic Garden – Outdoor Walks & Indoor Greenhouses

Address: 1000 Lake Cook Road, Glencoe, IL 60022
Phone: (847) 835-6801
Details: Explore 385 acres of scenic paths, seasonal garden walks and natural beauty or warm up inside the Garden’s greenhouses with year-round blooms. With family-friendly spaces like the Nature Play Garden, plus on-site dining and shopping, the Chicago Botanic Garden is a cozy winter destination. Visit the website for hours, admission and parking details.

The Second City – Live Comedy & Indoor Entertainment

Address: 230 W North Avenue, Chicago, IL 60614
Phone: (312) 337-3992
Details: A Chicago institution since 1959, The Second City is the birthplace of modern improv and sketch comedy, rooted in the groundbreaking games of Viola Spolin. The iconic venue has helped shape generations of performers while continuing to deliver sharp, fast-paced shows year-round. Visit the website for current performances and ticket information.

I|O Godfrey Roofscape – Rooftop Lounge & Winter Igloos

Address: 127 West Huron at Lasalle, Chicago, IL 60654
Phone: (312) 374-1830
Details: Chicago’s largest year-round rooftop lounge features a retractable roof that creates a true indoor-outdoor experience in any season. Guests can enjoy chef-crafted cocktails and small plates daily, with brunch served Saturdays and Sundays from 11 a.m. to 2:30 p.m., and warm up in signature Winter Wonderland igloos during the colder months. Visit the website to reserve an igloo or plan your rooftop experience.

Want ideas that fit your family and your budget? Enter your ZIP code and preferences — kid-friendly, outdoor, educational and more — for winter getaway recommendations made for you.

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