Chicago Holiday Walking Tour: The Loop’s Festive Highlights

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This self-guided tour is perfect for guests that cannot join a scheduled Chicago Holiday Walking Tour.

Welcome to our self-guided Chicago Holiday Walking Tour! Experience the magic of the holiday season in the heart of the Windy City. This tour will take you through some of Chicago’s most iconic landmarks, all dressed up in their festive best. Along the way, you’ll discover rich histories, enchanting decorations, and heartwarming stories that embody the spirit of the holidays in Chicago.

Stop 1: Millennium Park Christmas Tree and Ice Skating Rink

201 E Randolph St, Chicago, IL 60602

What to See

  • Chicago’s Official Christmas Tree: Admire the towering Christmas tree adorned with thousands of twinkling lights and ornaments.
  • McCormick Tribune Ice Rink: Watch skaters glide under the city skyline or rent skates yourself for a memorable experience.
  • Cloud Gate (“The Bean”): Don’t miss this iconic sculpture reflecting the festive surroundings.

Points of Interest

  • Photo Opportunities: Capture the festive atmosphere with the illuminated tree and skyline as your backdrop.
  • Holiday Music: Enjoy seasonal tunes often played around the rink and tree area.

Stories to Share

  • Chicago’s Christmas Tree Tradition: In 1913, Chicago lit its first municipal Christmas tree, a 35-foot Douglas spruce, in Grant Park. Mayor Carter Harrison Jr. dedicated it as a symbol of hope and unity.
  • Transformation of Millennium Park: Once a desolate rail yard, the park opened in 2004 and has become a central hub for Chicago’s cultural and holiday festivities.
  • “The Bean” in Winter: Designed by Anish Kapoor, the Cloud Gate sculpture offers a unique view during the holidays, reflecting the lights and snow, creating a magical visual effect.

Stop 2: Chicago Cultural Center

Address: 78 E Washington St, Chicago, IL 60602

What to See

  • Preston Bradley Hall: Marvel at the world’s largest Tiffany stained-glass dome, measuring 38 feet in diameter.
  • Rotunda and Grand Staircase: Observe the intricate mosaics and marble detailing.
  • Holiday Exhibits: Check for seasonal art installations and free concerts.

Points of Interest

  • Warm Indoor Space: Take a break from the cold while enjoying the opulent interior.
  • Information Desk: Pick up brochures about current exhibits and events.

Stories to Share

  • A Palace for the People: Opened in 1897 as Chicago’s first public library, the building symbolized the city’s commitment to accessibility and education.
  • Architectural Marvel: The Beaux-Arts building was designed by Shepley, Rutan, and Coolidge, showcasing lavish materials and craftsmanship meant to inspire visitors.
  • Cultural Hub: Since 1991, it has served as the Chicago Cultural Center, hosting over 1,000 programs annually, all free to the public.

Stop 3: Macy’s on State Street (Formerly Marshall Field’s)

Address: 111 N State St, Chicago, IL 60602

What to See

  • Holiday Window Displays: Stroll along State Street to view the elaborate, themed displays enchanting visitors since the early 1870s.
  • The Walnut Room: Located on the 7th floor, it’s home to the Great Tree, a two-story Christmas tree decorated with hundreds of ornaments.
  • Tiffany Ceiling: Inside the store, look up to see the largest unbroken example of Tiffany Favrile glass in the world.

Points of Interest

  • Dining Experience: Consider making a reservation at The Walnut Room to dine next to the Great Tree.
  • Shopping and Souvenirs: Explore unique gifts and holiday specials throughout the store.

Stories to Share

  • Marshall Field’s Legacy: Established in 1852, the store became a retail pioneer, introducing concepts like the bridal registry and in-store dining.
  • Holiday Windows Tradition: The animated window displays began in the early 20th century, delighting generations with stories like “A Christmas Carol” and “The Nutcracker.”
  • The Great Tree: Since 1907, the Walnut Room has featured a grand Christmas tree, becoming a cherished Chicago tradition.
  • Transition to Macy’s: In 2006, Marshall Field’s was rebranded as Macy’s, sparking local debate but continuing the store’s holiday customs.

Stop 4: The Palmer House, A Hilton Hotel

Address: 17 E Monroe St, Chicago, IL 60603

What to See

  • Grand Lobby: Admire the French Baroque-style ceiling frescoes, chandeliers, and the majestic “Winged Angels” on the grand staircase.
  • Historical Displays: Find exhibits showcasing the hotel’s rich history and famous guests.
  • Lockwood Bar and Restaurant: A cozy spot to warm up with a drink or snack.

Points of Interest

  • Art and Architecture: Pay attention to the intricate designs by architect John M. Van Osdel.
  • Palmer House Brownies: Try the original brownie recipe created here.

Stories to Share

  • A Love Story Built in Stone: Potter Palmer built the original hotel as a wedding gift for his wife, Bertha Honore Palmer. After it burned down in the Great Chicago Fire of 1871, he rebuilt it grander than before.
  • Innovation and Luxury: The rebuilt Palmer House was the nation’s first fireproof hotel and featured modern amenities like electric light bulbs, telephones, and elevators.
  • Invention of the Brownie: In 1893, Bertha Palmer requested a portable dessert for ladies attending the World’s Columbian Exposition, leading to the creation of the chocolate fudge brownie.
  • Famous Guests: The hotel has hosted luminaries like Charles Dickens, Oscar Wilde, Judy Garland, and every U.S. president since Ulysses S. Grant.

Stop 5: Christkindlmarket Chicago at Daley Plaza

Address: 50 W Washington St, Chicago, IL 60602

What to See

  • Festive Market Booths: Explore over 50 vendors selling handmade ornaments, nutcrackers, cuckoo clocks, and other gifts.
  • Culinary Delights: Enjoy German specialties like bratwurst, schnitzel, potato pancakes, and Glühwein (hot spiced wine) served in collectible mugs.
  • Daley Plaza Christmas Tree: A beautifully decorated tree that serves as the market’s centerpiece.
  • The Picasso Sculpture: An untitled 50-foot steel sculpture by Pablo Picasso.

Points of Interest

  • Live Entertainment: Check the schedule for carolers, dance performances, and appearances by the Christkind.
  • Souvenir Mugs: Each year features a new mug design—great keepsakes!

Stories to Share

  • German Heritage in Chicago: In the 19th century, German immigrants were the largest ethnic group in Chicago, greatly influencing the city’s culture and traditions.
  • Origin of Christkindlmarket: Established in 1996, it was inspired by the 16th-century Christkindlesmarkt in Nuremberg, Germany. It’s now the largest Christmas market in the U.S.
  • The Christkind: A fairy-like being from German folklore who brings gifts to children. The market’s Christkind opens the event with a prologue.
  • The Picasso Sculpture: Unveiled in 1967, it was initially met with mixed reactions but has since become a beloved landmark. Its abstract form adds a modern contrast to the traditional market.

Additional Tips

  • Stay Warm: Between stops, consider warming up with a hot beverage from local cafes like Intelligentsia Coffee (53 E Randolph St) or Caffè Rom (200 S Michigan Ave).
  • Accessibility: The route is wheelchair and stroller friendly.
  • Plan Ahead: Check the operating hours of Christkindlmarket and The Walnut Room, especially if visiting on a holiday.

This festive tour showcases the heart and history of Chicago’s holiday celebrations. From glittering lights to timeless traditions, each stop offers a unique glimpse into what makes the season special in the Windy City. We hope this journey fills you with joy and creates lasting memories. Happy Holidays!