Holidays in the Windy City | Chicago, Illinois

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As one of the most populous cities in America, Chicago is a bustling destination that’s full of charm. While many travelers flock to warmer climates in the winter, the holiday season is one of the best times to visit the famous windy city. Explore the sights, soak in the culture, and marvel at the stunning architecture. 

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Kinzie Hotel – Explore Chicago Package

The Kinzie Hotel is a stylish boutique property that puts you in the heart of Chicago’s downtown hub. Situated along the iconic city skyline, you’re just minutes away from incredible dining, world-class museums, and popular attractions. Unwind in your chic guestroom and take in sweeping views of the city. The hotel offers a free continental breakfast each morning and a cocktail reception in the evenings. Discover the city’s unique culture and flavor with the Explore Chicago Package. It includes a CityPASS to Chicago’s famous museums, local Fannie May Chocolate and Garrett Popcorn, and free Wi-Fi for unlimited devices.

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Art Institute of Chicago

Founded in 1978, the Art Institute of Chicago is one of the largest and oldest art museums in the country. Its permanent collection spans nearly 300,000 works and they host over 30 special exhibitions a year. The museum is open year-round, but the holidays are even more spectacular. The famous lion statues out front are decorated with festive wreaths, and special holiday exhibitions are on display. See the elaborately decorated Holiday Thorne Rooms in Gallery 11. The miniature displays are decked out with beautifully detailed seasonal decorations.

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Millennium Park/Ice Rink

No visit to Chicago is complete without a trip to the renowned Millennium Park. The modern park is full of state-of-the-art architecture and stunning outdoor art. During the holidays, the park transforms into a winter wonderland complete with decorations, caroling, a lavish tree, and a free ice-skating rink! Stroll around the park and spend your afternoon people watching, then pick up a snack and quench your thirst at the Goose Island Beer Garden.

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Revival Food Hall

Revival Food Hall is a lively, all-local dining concept that highlights the best of Chicago’s culinary scene. Find the 24,000 square foot marketplace on the ground floor of The National in the center of Chicago’s business district. Eat your way through 15 fast-casual stalls featuring some of the city’s favorite neighborhood eateries. Don’t miss the “All Hall Happy Hour” every afternoon, where select vendors offer discounted specials. Warm up with Mindy’s famous hot chocolate at HotChocolate Bakery, the perfect treat for the holiday season.

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360 Chicago and the Signature Lounge

Make your way to the top of the John Hancock Building to experience the 360 Chicago Observation Deck. The observatory is located on the 94th floor and offers unmatched views of the city and Lake Michigan. While you’re up there, visit The Signature Lounge on the 96th floor and unwind with a drink as you gaze over Chicago. They serve a variety of specialty cocktails, wine, craft beer, and small bites.