Holidays at Skydeck!
Jan2
Festivals, Fairs & Special Events

Holidays at Skydeck!

HOLIDAYS @ SKYDECK CHICAGO! Celebrate the season from 103 stories above the city at Holidays @ Skydeck! Skydeck’s lower-level Chicago museum and observation deck will…

Friday January 2, 2026
Skydeck Chicago
233 S Wacker Dr.
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.
Not a Soft Thing: A Group Exhibition by Artist Mothers
Jan2
Museums, Galleries & Exhibitions

Not a Soft Thing: A Group Exhibition by Artist Mothers

Not a Soft Thing is a multifaceted exhibition by 15 artist/mothers spanning diverse cultural backgrounds, disciplines, and stages of caregiving. Together, this artist collective challenges…

Friday January 2, 2026
10:00 a.m.4:45 p.m.
Chicago Cultural Center
78 E Washington St
Homeschool Days at PEPPA PIG World of Play Chicago
Jan2
Tours & Attractions

Homeschool Days at PEPPA PIG World of Play Chicago

Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…

Friday January 2, 2026
10:00 a.m.5:00 p.m.
Peppa Pig World of Play Chicago
5 Woodfield Mall
Illinois Holocaust Museum presents Experience360
Jan2
Museums, Galleries & Exhibitions

Illinois Holocaust Museum presents Experience360

Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…

Friday January 2, 2026
10:00 a.m.5:00 p.m.
Illinois Holocaust Museum presents Experience360
360 N State St
Take Care with Peanuts: The Exhibit
Jan2
Museums, Galleries & Exhibitions

Take Care with Peanuts: The Exhibit

Good grief! Join Charlie Brown and the Peanuts Gang at Chicago Children’s Museum! Step into Take Care with Peanuts: The Exhibit and be transported into…

Friday January 2, 2026
10:00 a.m.5:00 p.m.
Chicago Children’s Museum
700 E. Grand Ave.
American Prophets: Writers, Religion, and Culture
Jan2
Museums, Galleries & Exhibitions

American Prophets: Writers, Religion, and Culture

American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…

Friday January 2, 2026
10:00 a.m.5:00 p.m.
American Writers Museum
180 N. Michigan Ave.
Museum of Ice Cream’s Pinkmas
Jan2
Museums, Galleries & Exhibitions

Museum of Ice Cream’s Pinkmas

Pinkmas at Museum of Ice Cream is officially back for the season, step into the sweetest holiday celebration of the season, happening now through January…

Friday January 2, 2026
10:00 a.m.7:00 p.m.
435 N Michigan Ave Suite G, Chicago, IL 60611
435 N Michigan Ave. Suite G
Pilsen Day Trip
Jan2
Festivals, Fairs & Special Events, Tours & Attractions

Pilsen Day Trip

We’re excited to host a Pilsen Day Trip Passport for visitors to shop local, shop small for their holiday shopping needs or for anyone who…

Friday January 2, 2026
10:00 a.m.7:00 p.m.
Pilsen Commercial Corridor, 18th Street from Damen to Morgan
W 18th St & S Damen Ave
McCormick Tribune Ice Rink
Jan2
Sports & Recreation

McCormick Tribune Ice Rink

Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…

Friday January 2, 2026
11:00 a.m.10:30 p.m.
Millennium Park
201 E Randolph St
Seadog Architecture Tour on the Chicago River
Jan2
Tours & Attractions

Seadog Architecture Tour on the Chicago River

Soak in unobstructed views of Chicago’s world-famous architecture with an exciting 45-minute ride on our Seadog Chicago River Architecture Tour! Starting right on the Chicago…

Friday January 2, 2026
12:30 p.m.1:30 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
The Beauty of Chicago
Jan2
Museums, Galleries & Exhibitions

The Beauty of Chicago

An ongoing showcase celebrating the people, places, and stories that define our city. Forum 301 Chicago will be hosting local Chicago artist to showcase their…

Friday January 2, 2026
2:00 p.m.9:00 p.m.
Forum 301 Chicago
301 W Ohio
Champagne Row, by Park Hyatt Chicago
Jan2
Festivals, Fairs & Special Events

Champagne Row, by Park Hyatt Chicago

CHAMPAGNE ROW, by Park Hyatt Chicago Thu – Sat, 3-8pm Reserve Your Seat   |   View Menu   Park Hyatt Chicago hosts an intimate champagne experience…

Friday January 2, 2026
3:00 p.m.8:00 p.m.
Park Hyatt Chicago
800 N. Michigan Ave
Holiday Magic
Jan2
Festivals, Fairs & Special Events

Holiday Magic

We’re lighting up the night this holiday season! Returning with a brand new light display, celebrate more than 40 years of Holiday Magic. Now with…

Friday January 2, 2026
3:00 p.m.9:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
The Glenlivet 55 Legacy Experience, by Park Hyatt Chicago
Jan2
Festivals, Fairs & Special Events

The Glenlivet 55 Legacy Experience, by Park Hyatt Chicago

Park Hyatt Chicago presents a singular offering centered on The Glenlivet 55 Year Old – Edition No. 1 of The Eternal Collection. Matured for more…

Friday January 2, 2026
5:00 p.m.7:00 p.m.
Park Hyatt Chicago
800 N. Michigan Ave
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
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
Chicago Bulls vs. Orlando Magic
Jan2
Friday January 2, 2026
7:00 p.m.8:30 p.m.
United Center
1901 W Madison St,
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Jan2
Theatre & Performing Arts

Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival

Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen.  For nearly four decades,…

Friday January 2, 2026
7:00 p.m.9:30 p.m.
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
Teatro Zinzanni
Jan2
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Friday January 2, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Krampus: The Fright Before Christmas
Jan2
Festivals, Fairs & Special Events, Tours & Attractions

Krampus: The Fright Before Christmas

We have transformed our haunted house into a Christmas wonderland, although it won’t be all glitter and snowflakes. You better watch out. You better not…

Friday January 2, 2026
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd