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Big Bus Tours’ Hop-On, Hop-Off Tour
Dec29
Tours & Attractions

Big Bus Tours’ Hop-On, Hop-Off Tour

Big Bus Tours’ daily Hop-On, Hop-Off tours offer visitors a convenient way to explore Chicago’s vibrant downtown, including historic landmarks, cultural institutions and hidden gems.…

Monday, December 29th
10:00 a.m.5:00 p.m.
The Phantom of the Opera
Dec30
Theatre & Performing Arts

The Phantom of the Opera

THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…

Tuesday, December 30th
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
By A Thread: Nature’s Resilience
Dec30
Museums, Galleries & Exhibitions

By A Thread: Nature’s Resilience

By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…

Tuesday, December 30th
10:00 a.m.4:00 p.m.
Big Bus Tours’ Hop-On, Hop-Off Tour
Dec30
Tours & Attractions

Big Bus Tours’ Hop-On, Hop-Off Tour

Big Bus Tours’ daily Hop-On, Hop-Off tours offer visitors a convenient way to explore Chicago’s vibrant downtown, including historic landmarks, cultural institutions and hidden gems.…

Tuesday, December 30th
10:00 a.m.5:00 p.m.
Tuesday Good Show
Dec30
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, December 30th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
The Phantom of the Opera
Dec31
Theatre & Performing Arts

The Phantom of the Opera

THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…

Wednesday, December 31st
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
By A Thread: Nature’s Resilience
Dec31
Museums, Galleries & Exhibitions

By A Thread: Nature’s Resilience

By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…

Wednesday, December 31st
10:00 a.m.4:00 p.m.
Big Bus Tours’ Hop-On, Hop-Off Tour
Dec31
Tours & Attractions

Big Bus Tours’ Hop-On, Hop-Off Tour

Big Bus Tours’ daily Hop-On, Hop-Off tours offer visitors a convenient way to explore Chicago’s vibrant downtown, including historic landmarks, cultural institutions and hidden gems.…

Wednesday, December 31st
10:00 a.m.5:00 p.m.
Tropical Wednesdays
Dec31
Tours & Attractions

Tropical Wednesdays

Immerge yourself in a cultural experience as Latin dances come alive on Taylor street – Salsa, Bachata, Cumbia, and Cha Cha Cha with margarita!

Wednesday, December 31st
6:00 p.m.8:00 p.m.
Vintage Bar Chicago
1449 W. Taylor St.
Hooch & Holler Comedy Show
Dec31
Music & Comedy, Theatre & Performing Arts

Hooch & Holler Comedy Show

Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…

Wednesday, December 31st
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Phantom of the Opera
Jan1
Theatre & Performing Arts

The Phantom of the Opera

THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…

Thursday January 1, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
By A Thread: Nature’s Resilience
Jan1
Museums, Galleries & Exhibitions

By A Thread: Nature’s Resilience

By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…

Thursday January 1, 2026
10:00 a.m.4:00 p.m.
Teatro Zinzanni
Jan1
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Thursday January 1, 2026
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Improvsed DCOM
Jan1
Music & Comedy, Theatre & Performing Arts

Improvsed DCOM

Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…

Thursday January 1, 2026
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Phantom of the Opera
Jan2
Theatre & Performing Arts

The Phantom of the Opera

THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…

Friday January 2, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Comedy Hour at Annoyance Theatre
Jan2
Jan3
Theatre & Performing Arts

Comedy Hour at Annoyance Theatre

Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…

Friday January 2, 2026
12:00 a.m.Saturday January 3, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
By A Thread: Nature’s Resilience
Jan2
Museums, Galleries & Exhibitions

By A Thread: Nature’s Resilience

By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…

Friday January 2, 2026
10:00 a.m.4:00 p.m.
Wicker Park Bucktown’s “First Fridays” Art Walk
Jan2
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday January 2, 2026
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
Teatro Zinzanni
Jan2
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Friday January 2, 2026
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
Jan2
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Friday January 2, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Jan2
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday January 2, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Jan2
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday January 2, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Improvised Shakespeare Company®
Jan2
Theatre & Performing Arts

The Improvised Shakespeare Company®

The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…

Friday January 2, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
Jan2
Music & Comedy

Devil’s Daughter

The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday January 2, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
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