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Question

Hello! I have been having a difficult time planning my trip to Chicago! I want to know everyone's opinion on whether Christmas or New Year's is the best time to visit Chicago! Please help a girl out! Thank you!!!

Answer

Deciding between visiting Chicago at Christmas or New Year’s depends on what kind of experience you’re looking for, as both have their own unique charm, activities, and considerations.

Christmas in Chicago

Christmas is a magical time in Chicago, with festive decorations, holiday markets, and winter activities throughout the city. The city is beautifully lit, and there’s a cozy, festive atmosphere that makes it ideal for sightseeing and enjoying seasonal events.

Magnificent Mile Lights Festival — elaborate holiday lights, parades, and performances.
Christkindlmarket — a traditional German-style Christmas market at Daley Plaza, perfect for shopping for gifts, seasonal treats, and mulled wine.
Ice skating at Millennium Park or Maggie Daley Park — iconic and picturesque for photos and family fun.
Holiday displays at Macy’s and other department stores — great for browsing and soaking in the festive mood.
Musical performances, holiday-themed shows, and concerts — often easier to book than around New Year’s.

New Year’s in Chicago

New Year’s is more about celebrations, parties, and a high-energy atmosphere. Expect large crowds, special events, and fireworks at midnight. It’s an exciting time if you enjoy nightlife and big city celebrations.

Fireworks at Navy Pier — one of the biggest New Year’s events in the city.
Special restaurant and hotel packages for New Year’s Eve — can be pricier, so early booking is essential.
Bars, clubs, and music venues — lively atmosphere but often crowded and more expensive than usual.
Winter outdoor activities — ice skating and seasonal sights still available, though the focus is more on parties and countdown events.

Additional Considerations

Weather — both times are cold, often below freezing, with December having a slightly higher chance of snow around Christmas, which adds to the holiday charm.
Crowds — Christmas is busy with tourists enjoying family activities, but New Year’s is especially crowded downtown due to events and celebrations.
Accommodation costs — hotels may be more expensive for New Year’s Eve than Christmas week.
Family vs. social experience — Christmas is better for family-friendly sightseeing, markets, and festive décor, while New Year’s is better for social, nightlife-oriented experiences.

In summary, if you want a festive, cozy holiday atmosphere with opportunities for sightseeing, Christmas is ideal. If you want to experience the city’s vibrant celebrations and party scene, New Year’s is the way to go. Either way, Chicago in the winter offers iconic sights, lights, and activities, so plan ahead for weather and bookings.

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