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12 Must-Do, Fresh, And Unique Things To Do In Chicago This Winter 2025/2026

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Planning a trip to the Windy City? As of December 24, 2025, Chicago is buzzing with a mix of iconic landmarks and brand-new, must-see attractions that make it a premier destination, especially during the festive winter season. Whether you're a first-time visitor eager to see the famous "Bean" or a seasoned traveler looking for the latest hidden gems, this guide is packed with the most current and unique experiences to ensure your Chicago itinerary is unforgettable.

Forget the stale, outdated lists—we've researched the newest exhibits, hottest entertainment venues, and freshest culinary tours. From soaring above the skyline in a virtual flight experience to exploring world-class art and indulging in a Holiday Hike Festive Food Tour, prepare to discover the absolute best of what to do in Chicago right now, blending classic Chicago charm with exciting 2025 updates.

The Newest Must-See Chicago Attractions for 2025/2026

Chicago's landscape is constantly evolving, and a handful of new attractions and venues have recently opened or are featuring fresh exhibits that are essential viewing for any visitor in late 2025 and early 2026. Prioritize these unique experiences to make your trip truly current.

  • Experience Flyover in Chicago: The Ultimate Virtual Flight: Touted as Chicago's best new attraction by USA TODAY, Flyover Chicago offers an immersive flight ride experience. This attraction connects you with the sights, sounds, and spirit of the city from an entirely new perspective, using a massive screen and special effects to simulate soaring over the iconic skyline and landmarks.
  • Explore The Salt Shed and The Three Top Lounge: Goose Island has a new entertainment hub. The Salt Shed, a spacious indoor-outdoor event space, recently unveiled its new venue, which includes a stylish cocktail bar called The Three Top Lounge. This is the spot to catch a live show or enjoy a sophisticated drink in a cutting-edge setting.
  • Catch the New 2025 Museum Exhibits: Chicago's world-renowned museums are featuring fresh content. At the Field Museum, don't miss the highly anticipated Pokémon Fossil Museum exhibit. For families, the Chicago Children's Museum is hosting the charming Take Care with Peanuts: The Exhibit. These temporary features make a visit to these classic institutions feel brand new.

Essential Chicago Landmarks and Iconic Experiences

No trip to Chicago is complete without checking off the bucket-list items. These are the classic attractions that define the city, offering a mix of stunning architecture, world-class art, and unforgettable views.

The Thrill of the Skyline: Willis Tower and Millennium Park

The city's architecture is a key entity of the Chicago experience. You must see it from above and at ground level.

Willis Tower Skydeck: Head to the Willis Tower (formerly Sears Tower) and step out onto the Skydeck. The Ledge, a glass balcony extending four feet from the building, offers a heart-stopping view 1,353 feet above the city. It's the perfect spot for an adrenaline rush and unparalleled photo opportunities of the metropolitan area.

Millennium Park and "The Bean": A visit to Millennium Park is essential. The park is home to the iconic Cloud Gate sculpture, affectionately known as "The Bean." Stroll through the park, admire your distorted reflection in the stainless steel, and take in the surrounding skyscrapers. It’s a quintessential Chicago moment.

The Art Institute of Chicago: Located just steps from Millennium Park, the Art Institute is one of the oldest and largest art museums in the United States. It houses an extraordinary collection, including masterpieces like Grant Wood’s American Gothic and works by Monet and Van Gogh. Allow several hours to truly appreciate its depth.

Unique Winter Activities and Culinary Adventures

Visiting during the winter months of 2025/2026 unlocks a special set of activities, from festive markets and holiday cheer to deep-dive culinary tours. These experiences provide a local flavor that goes beyond the typical tourist traps.

  • Ice Skating at Maggie Daley Park: Skip the traditional rink and glide along the unique ice skating ribbon at Maggie Daley Park. This winding path offers a more scenic and dynamic skating experience surrounded by the beautiful city skyline. It’s one of the best winter things to do in Chicago.
  • Navy Pier's Winter WonderFest: From late 2025 through early January 2026, Navy Pier transforms into a festive holiday destination. The Winter WonderFest returns, offering a magical indoor experience complete with a towering 42-foot Holiday Tree, light displays, and endless holiday cheer, making it a perfect family outing.
  • Walk the Chicago Riverwalk: Even in winter, the Chicago Riverwalk is a stunning place for a stroll. This pedestrian path along the main branch of the Chicago River offers unique perspectives of the city's famous architecture. Many boat tours may be seasonal, but the walk itself is open year-round for a peaceful urban exploration.
  • Indulge in a Holiday Hike Festive Food Tour: For a truly unique and delicious experience, join a Holiday Hike Festive Food Tour. These gourmet tours allow you to sample the best of Chicago's culinary scene while enjoying the festive holiday decorations and learning about the city's rich history.
  • Dive into Deep-Dish and Culinary Tours: No Chicago trip is complete without deep-dish pizza. But to elevate your food journey, consider a dedicated culinary tour. Companies like Chef Driven Food Tours or Sidewalk Food Tours offer guided adventures to taste everything from authentic tapas to iconic American doughnuts, ensuring you get a true taste of the city's diverse food culture.

Neighborhood Exploration: Beyond The Loop

To gain topical authority and a genuine feel for Chicago life, you must venture into its distinct neighborhoods. Each area offers a different vibe, from historic architecture to trendy dining scenes.

The West Loop: Chicago's Restaurant Row: Once an industrial area, the West Loop has transformed into the city's premier dining destination. Explore Randolph Street, known as "Restaurant Row," where you'll find some of the nation's most acclaimed chefs and innovative cuisine. It’s a must-visit for any foodie.

Pilsen and Logan Square: Art and Culture Hubs: Head south to Pilsen (Little Mexico) to see vibrant street art and murals, a testament to its rich cultural heritage. Meanwhile, Logan Square offers a mix of historic boulevards, trendy bars, and independent boutiques, perfect for those looking for a laid-back, creative atmosphere.

Lincoln Park: Green Space and Zoo: Lincoln Park is an affluent neighborhood known for its vast parks, shopping, and the free-admission Lincoln Park Zoo. It's a beautiful escape from the downtown hustle, offering a blend of nature and city life.

Chinatown and Greektown: For a global culinary and cultural experience, visit Chinatown for authentic Chinese cuisine and architecture, or Greektown for a taste of the Mediterranean. These ethnic enclaves are vital entities in Chicago's cultural tapestry.

Chicago Entities and LSI Keywords for Your Trip

To enhance your travel planning, keep these key entities and LSI (Latent Semantic Indexing) keywords in mind for better search results and a deeper understanding of the city:

  • Transportation: CTA (Chicago Transit Authority), 'L' Train, O'Hare International Airport (ORD), Midway International Airport (MDW).
  • Architecture/Tours: Architecture River Cruise, Chicago Cultural Center, Tribune Tower, Wrigley Building.
  • Food & Drink: Deep-dish pizza, Italian beef, Chicago-style hot dog, craft breweries, speakeasies.
  • Culture: Second City Comedy Club, Chicago Theatre, Field Museum, Shedd Aquarium, Adler Planetarium.
  • Sports: Wrigleyville (Cubs), Soldier Field (Bears), United Center (Bulls/Blackhawks).

By focusing on these fresh attractions, classic landmarks, and unique neighborhood experiences, your 2025/2026 visit to Chicago will be filled with discovery, excitement, and unforgettable memories. Enjoy your time in the heart of the Midwest!

12 Must-Do, Fresh, and Unique Things to Do in Chicago This Winter 2025/2026
what to do in chicago
what to do in chicago

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