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Christmas in Chicago

December 12-14, 2025

Book Now!

Trip Details

🎄 Experience Christmas in Chicago
​
Starting at $280 per person
Holiday Getaway by Train | Hosted by Baraboo Tours

🏙️ A Festive Escape to the Windy City
Join Baraboo Tours for a magical Christmastime experience in downtown Chicago. Travel by train and enjoy an overnight stay in the heart of the city, surrounded by lights, music, shopping, and seasonal joy.

🚆 What’s Included
  • Overnight Hotel Stay in Downtown Chicago
    A cozy, central location perfect for holiday exploring.
  • Amtrak Train Travel
    Depart from Milwaukee, Wisconsin Dells, or La Crosse and ride in comfort to Chicago.
  • Flexible Itinerary
    Shelley will help curate the perfect holiday experience just for you!

🎁 Suggested Activities
  • 🎄 Visit Christkindlmarket for German-style holiday shopping
  • 🌟 See the iconic Christmas Tree at Millennium Park
  • ⛸️ Go Ice Skating at the Bean
  • 🍹 Enjoy rooftop drinks in an igloo at The Godfrey Hotel
  • 🍵 Or warm up with high tea at The Peninsula Hotel
Shelley can help you plan the perfect festive itinerary!

💸 Pricing (Based on Double Occupancy)
  • $280 – Early bird rate, book by July 15
  • $300 – Book by August 1 ($400 single occupancy)
  • $350 – Book by September 1 ($450 single occupancy)
  • $400 – Last chance to book by October 1

🎅 Book Your Holiday Getaway! Travel light, sip hot cocoa, and feel the magic of the season — Baraboo Tours takes care of all the details so you can simply enjoy.
✨ Big-City Cheer. Small-Town Support.


Trip Insurance - Why you should consider getting trip insurance.

Trip insurance is a valuable safeguard that provides financial protection and peace of mind in case unexpected events disrupt your travel plans. It can cover a range of situations, such as trip cancellations, delays, lost luggage, medical emergencies, or unforeseen circumstances that may arise before or during your journey. Reaching out to Shelley for trip insurance ensures you get expert advice tailored to your needs and coverage options that align with your travel plans. Shelley is dedicated to helping you protect your investment and enjoy a worry-free experience, so you can focus on making lasting memories.

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