March 10-19, 2025
April 5-12, 2025
April 9-14, 2025
April 29 - May 8, 2025
SOLD OUT
June 17-26, 2025
July 7-19, 2025
SOLD OUT
July 29-August 2, 2025
August 7-22, 2025
August 24-30, 2025
September 2-4, 2025
September 2-4, 2025
September 8-13, 2025
SOLD OUT
October 1-3, 2025
October 7-11, 2025
October 20-26, 2025
November 2-8, 2025
November 2025
November 24-29, 2025
December 6-7, 2025
Embrace the magic of the holiday season with an unforgettable overnight stay on Chicago’s iconic Magnificent Mile. Stroll through the twinkling lights, shop to your heart’s content, and soak in the festive energy of the Windy City.
Visit Chicago’s Christkindlmarkt, a charming European-style Christmas market where you can savor mulled wine, find unique gifts, and enjoy the warmth of holiday traditions. With plenty of free time to explore the Magnificent Mile, this trip offers the perfect blend of relaxation and holiday cheer.
Don’t miss your chance to experience Chicago at its most magical—reserve your spot today!
December 12-14, 2025
Embrace the magic of the holiday season with an unforgettable overnight stay on Chicago’s iconic Magnificent Mile. Stroll through the twinkling lights, shop to your heart’s content, and soak in the festive energy of the Windy City.
Visit Chicago’s Christkindlmarkt, a charming European-style Christmas market where you can savor mulled wine, find unique gifts, and enjoy the warmth of holiday traditions. With plenty of free time to explore the Magnificent Mile, this trip offers the perfect blend of relaxation and holiday cheer.
Don’t miss your chance to experience Chicago at its most magical—reserve your spot today!
December 13-14, 2025
Embrace the magic of the holiday season with an unforgettable overnight stay on Chicago’s iconic Magnificent Mile. Stroll through the twinkling lights, shop to your heart’s content, and soak in the festive energy of the Windy City.
Visit Chicago’s Christkindlmarkt, a charming European-style Christmas market where you can savor mulled wine, find unique gifts, and enjoy the warmth of holiday traditions. With plenty of free time to explore the Magnificent Mile, this trip offers the perfect blend of relaxation and holiday cheer.
Don’t miss your chance to experience Chicago at its most magical—reserve your spot today!
January 25-29, 2026
February 1-5, 2026
March 1-10, 2026