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$50 Off
Chicago HO HO Holiday! December 3-5, 2026

Celebrate the holidays with a festive weekend getaway to Chicago! Explore the beautifully decorated Macy’s on State Street and the elegant Driehaus Museum, stay two…
1 Person
Duration 1 Day
From $1049 $999 You save $50
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$10 Off
Broadway in Chicago: Operation Mincemeat -OPEN for Registration! Save your spot today!

Sunday, October 11, 2026
1 Person
Duration 1 Day
From $339 $329 You save $10
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$10 Off
Don’t Miss Your Chance! Come From Away at the Marriott Theatre –On hold – please email: holly@hollitudeholidaytravel.com

Wednesday, October 14, 2026
1 Person
Duration 1 Day
From $189 $179 You save $10
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$10 Off
Lessons of Hope: Anne Frank at the Griffin Museum

Tuesday, October 27, 2026
1 Person
Duration 1 Day
From $199 $189 You save $10
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$10 Off
Inside Wisconsin’s Food & Farm Story

Thursday, October 22, 2026
1 Person
Duration 1 Day
From $169 $159 You save $10
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$10 Off
Cranberry Craze~! Visit to Warren’s Cranberry Festival

Friday, September 25, 2026
1-30 People
Duration 1 Day
From $159 $149 You save $10
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$10 Off
Monuments & Masterpieces: History Behind Sacred Stones and Tiffany Glass — This trip is currently full. Please email Holly@hollitudeholidaytravel.com to be placed on the waitlist. If I have enough on the waitlist, I will open a new trip date.

Thursday, September 10, 2026
1-14 People
Duration 1 Day
From $159 $149 You save $10
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$10 Off
Broadway in Chicago: “Oh, Mary!”

Saturday, February 6, 2027 Matinee
1-29 People
Duration 1 Day
From $339 $329 You save $10
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$150 Off
Roses, Racing, & Bourbon: A Derby Getaway April 29 – May 2, 2027

Back by popular demand, Holly and James invite you back to Kentucky for an unforgettable blend of excitement, education, and Southern charm—centered around the most…
Medium 1 Person
Duration 1 Day
From $3899 $3749 You save $150
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$50 Off
Great River Getaway

Sept 13-15, 2026
1-35 People
Duration 3 Days – 2 Nights
From $1039 $989 You save $50
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