Christmas Magic in Chicago: A 4-Day Holiday Itinerary Itinerary

Indulge in a festive brunch at The Signature Room at the 95th, offering stunning views of the city. Afterward, take a leisurely walk along the Chicago Riverwalk and enjoy the holiday decorations.

For lunch, head to Gibsons Bar & Steakhouse for a classic Chicago dining experience. Spend the afternoon exploring the Art Institute of Chicago, home to a world-class art collection.

In the evening, take a magical Christmas lights tour of the city, where you can see the most beautifully decorated neighborhoods. For dinner, enjoy a festive meal at Girl & The Goat, known for its innovative cuisine.

Start your day with a delicious brunch at Au Cheval, famous for its indulgent burgers. Afterward, visit the Christkindlmarket in Daley Plaza, where you can shop for unique gifts and enjoy traditional German treats.

For lunch, experience the vibrant atmosphere of Xoco, a top spot for Mexican cuisine. Spend the afternoon ice skating at Millennium Park Ice Rink and taking in the festive surroundings.

Enjoy a magical evening at the Chicago Symphony Orchestra's Merry, Merry Chicago!, a holiday concert that will fill you with joy and cheer. For a late-night bite, head to Lou Malnati's Pizzeria for some of the best deep-dish pizza in the city.

On this peaceful Christmas Eve morning, start your day with a serene walk along the Chicago Lakefront Trail, taking in the beauty of Lake Michigan. For a festive brunch, enjoy the holiday menu at The Publican, known for its farm-to-table cuisine.

Spend the afternoon exploring the 360 Chicago Observation Deck, where you can enjoy panoramic views of the city. For a late lunch, head to Frontera Grill for a taste of authentic Mexican flavors.

Conclude your Christmas in Chicago with a special holiday dinner at Alinea, a culinary experience that will truly be the highlight of your trip. Afterward, take a leisurely walk through the city to enjoy the Christmas lights and decorations one last time.