Chicago Loop Holiday Gift Guide
2 MIN READ – Crossing items off your holiday shopping list can be hard, especially when you’re drawing blanks. Get inspired by this Loop holiday gift guide that’ll surely draw nothing but smiles this holiday season.
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Chicago Loop Insights
Your insider's guide to the best things to do, see, and experience in Chicago.
What's Happening
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Chicago Architecture Center River Cruise Aboard First Lady
March 15, 2026
Chicago’s top-rated architecture boat tour, 90 minutes with expert CAC guides, stunning skyline views, open-air seating, and onboard amenities.
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Creepy Cruise
March 21, 2026
Explore Chicago’s haunted past on a nighttime river cruise featuring ghost stories, mob history, and eerie secrets of the Windy City.
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Sightseeing River & Lake Cruises
April 17, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
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Chicago by Night River & Lake
April 17, 2026
Experience Chicago at night on a 90-minute river and lake cruise, featuring a glittering skyline, cool breezes, and lively, family-friendly commentary.
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Theater of the Mind - with The Goodman
April 22, 2026
Directed by Andrew Scoville. Co-created by Academy, Grammy, and Tony Award-winning artist David Byrne* and writer Mala Gaonkar, Theater of the Mind is a new theatrical…
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THE MAGIC PARLOUR - Presented by The Goodman and Petterino's
September 4, 2026
Experience Jaw-Dropping Magic. Enter through the doors at 50 West Randolph to discover a hidden world where the impossible becomes…
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Jekyll & Hyde
September 8, 2026
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse…
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DEAD GIRL'S QUINCEAÑERA
September 26, 2026
Sept 26 - Nov 1, 2026 By Phanésia Pharel Directed by Melia Bensussen Detective skills: unverified. Determination: unmatched. FACT: Maria…
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The Chicks: Taking The Long Way 20th Anniversary
October 3, 2026
Thirteen-time Grammy® Award winners The Chicks celebrate two decades of the critically acclaimed album that topped the Billboard 200 chart…