The Holiday Hop
Dec6
Festivals, Fairs & Special Events, Music & Comedy, Tours & Attractions

The Holiday Hop

~a festive multi-tavern experience that will knock your stockings off~  Get ready to make merry at the 2nd annual Holiday Hop! This spirited event will…

Saturday, December 6th
12:00 p.m.7:00 p.m.
Wells St & Schiller St, Old Town
Seadog Architecture Tour on the Chicago River
Dec6
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…

Saturday, December 6th
12:30 p.m.1:30 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
The Art Deco Nutcracker: Chicago’s Sparkling Holiday Tradition Returns for Its 10th Anniversary
Dec6
Theatre & Performing Arts

The Art Deco Nutcracker: Chicago’s Sparkling Holiday Tradition Returns for Its 10th Anniversary

The stage lights are calling, and the magic is about to unfold. The award-winning A&A BALLET announces the return of its critically acclaimed Art Deco…

Saturday, December 6th
1:00 p.m.3:00 p.m.
Athenaeum Center for Thought & Culture
2936 N. Southport Ave. , Chicago, IL, 60657
Chicago River Sleigh Rides with Santa!
Dec6
Tours & Attractions

Chicago River Sleigh Rides with Santa!

🎅🚢 Set sail on the iconic Chicago River this holiday season with our Santa Claus Sleigh Ride Cruises! 🌟 Join us for an unforgettable experience…

Saturday, December 6th
1:00 p.m.7:00 p.m.
DuSable Harbor 200 N Breakwater Access
DuSable Harbor 200 N Breakwater Access
A Christmas Carol
Dec6
Theatre & Performing Arts

A Christmas Carol

“I will honor Christmas in my heart, and try to keep it all the year.” Rediscover a Dickens’ classic with an adaptation that “makes you…

Saturday, December 6th
2:00 p.m.
Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601
That’s Weird, Grandma: Holiday Party!
Dec6
Theatre & Performing Arts

That’s Weird, Grandma: Holiday Party!

It’s an annual holiday tradition! PlayMakers Laboratory’s is pleased to welcome back its original sketch show That’s Weird, Grandma: Holiday Party! Playing five performances only…

Saturday, December 6th
2:00 p.m.3:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Uniting Voices Chicago Presents Winter Glow! a Festive Concert at Chicago Symphony Center
Dec6
Music & Comedy

Uniting Voices Chicago Presents Winter Glow! a Festive Concert at Chicago Symphony Center

Uniting Voices Chicago performs the festive Winter Glow concert at Chicago Symphony Center, 220 S. Michigan Ave, on Saturday, Dec. 6 for two shows only,…

Saturday, December 6th
2:00 p.m.3:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
The Taming of the Shrew
Dec6
Theatre & Performing Arts

The Taming of the Shrew

Deception, disguise, and desire. What if we want to be tamed? The richest man in town has two daughters and one big problem: he refuses to marry…

Saturday, December 6th
2:00 p.m.4:00 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Much Ado About Nothing
Dec6
Theatre & Performing Arts

Much Ado About Nothing

Just in time for the holiday season, Shakespeare’s wittiest rom-com is “as merry as the day is long!” Beatrice is living it up as a…

Saturday, December 6th
2:00 p.m.4:30 p.m.
Chicago Shakespeare Courtyard Theater
800 E. Grand, Chicago, IL, 60611
Gingerbread Jubillee
Dec6
Festivals, Fairs & Special Events

Gingerbread Jubillee

Step into the magic of the season at Somerset’s Gingerbread Jubilee, a delightful winter celebration where holiday dreams come to life! Perfect for families, friends,…

Saturday, December 6th
2:00 p.m.5:00 p.m.
Somerset
1112 N State St
Holiday Market at The Digs Chicago
Dec6
Festivals, Fairs & Special Events

Holiday Market at The Digs Chicago

We’re so excited to invite you to the Digs Holiday Market! Save the date for Saturday, December 6th, from 2-6pm. Check out new pieces by…

Saturday, December 6th
2:00 p.m.6:00 p.m.
The Digs Chicago
333 N Oakley BLVD Suite #305
Superior Donuts
Dec6
Theatre & Performing Arts

Superior Donuts

Arthur Przybyszewski owns a decrepit donut shop in the Uptown neighborhood of Chicago. Franco Wicks, a black teenager who is his only employee, wants to…

Saturday, December 6th
3:00 p.m.5:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Oil Lamp Presents “It’s A Wonderful Life: A Live Radio Play”
Dec6
Theatre & Performing Arts

Oil Lamp Presents “It’s A Wonderful Life: A Live Radio Play”

Oil Lamp Theater is proud to present the final production in its 2025 season, It’s A Wonderful Life: A Live Radio Play, November 20 –…

Saturday, December 6th
3:00 p.m.5:00 p.m.
Oil Lamp Theater
1723 Glenview Rd, Glenview, IL, 60025
Friends with Guns by Stephanie Alison Walker
Dec6
Theatre & Performing Arts

Friends with Guns by Stephanie Alison Walker

November 7 – December 7 | The Den Theatre written by Stephanie Alison Walker directed by Nathan Dale Short assistant direction by Emma Leeper You…

Saturday, December 6th
3:00 p.m.5:30 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Friends with Guns by Stephanie Alison Walker
Dec6
Theatre & Performing Arts

Friends with Guns by Stephanie Alison Walker

You think you know your friends, your neighbors, your spouse; but what happens when you suddenly find out they have a garage full of guns?…

Saturday, December 6th
3:00 p.m.5:30 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Falstaff, ossia Le tre burle
Dec6
Theatre & Performing Arts

Falstaff, ossia Le tre burle

Chicago Opera Theater (COT) presents the highly anticipated Chicago premiere of Falstaff, ossia le tre burle by composer Antonio Salieri and librettist Carlo Prospero Defranceschi.…

Saturday, December 6th
3:00 p.m.5:30 p.m.
Fine Arts Building – Studebaker Theater
410 S. Michigan Avenue
Falstaff, ossia Le tre burle
Dec6
Theatre & Performing Arts

Falstaff, ossia Le tre burle

Chicago Opera Theater (COT) presents the highly anticipated Chicago premiere of Falstaff, ossia le tre burle by composer Antonio Salieri and librettist Carlo Prospero Defranceschi.…

Saturday, December 6th
3:00 p.m.5:30 p.m.
Fine Arts Building – Studebaker Theater
410 S. Michigan Avenue
Holiday Magic
Dec6
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…

Saturday, December 6th
3:00 p.m.9:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Chicago Puzzle Club & The Chicago Wolves – Teams Speed Puzzle Competition & Hockey Game Package
Dec6
Sports & Recreation

Chicago Puzzle Club & The Chicago Wolves – Teams Speed Puzzle Competition & Hockey Game Package

Chicago Puzzle Club and the Chicago Wolves are excited to collaborate and bring speed puzzling and hockey together! Teams of 4 will race to complete…

Saturday, December 6th
3:30 p.m.9:30 p.m.
Allstate Arena
6920 Mannheim Road
It’s a Wonderful Life: Live in Chicago!
Dec6
Theatre & Performing Arts

It’s a Wonderful Life: Live in Chicago!

George Bailey – the Everyman from small town Bedford Falls whose dreams of escape and adventure were stopped by family obligation and civic duty –…

Saturday, December 6th
4:00 p.m.5:30 p.m.
American Blues Theater
5627 N Lincoln Blvd
Sleigh the Canvas at the Sheraton Sleigh Bar
Dec6
Festivals, Fairs & Special Events, Theatre & Performing Arts

Sleigh the Canvas at the Sheraton Sleigh Bar

Sip, paint, and sleigh your holiday masterpiece during this festive sip & paint experience inside our holiday-themed Sheraton Sleigh Bar activation. On Saturday, December 6 from 4…

Saturday, December 6th
4:00 p.m.6:00 p.m.
Sheraton Grand Chicago Riverwalk
301 E. North Water Street
The Art Deco Nutcracker: Chicago’s Sparkling Holiday Tradition Returns for Its 10th Anniversary
Dec6
Theatre & Performing Arts

The Art Deco Nutcracker: Chicago’s Sparkling Holiday Tradition Returns for Its 10th Anniversary

The stage lights are calling, and the magic is about to unfold. The award-winning A&A BALLET announces the return of its critically acclaimed Art Deco…

Saturday, December 6th
5:00 p.m.7:00 p.m.
Athenaeum Center for Thought & Culture
2936 N. Southport Ave. , Chicago, IL, 60657
Michael Blaustein Tour 2025: The Taste Me
Dec6
Music & Comedy

Michael Blaustein Tour 2025: The Taste Me

Comedian Michael Blaustein will perform live at Vic Theatre on Dec. 6, 2025.

Saturday, December 6th
5:00 p.m.10:00 p.m.
The Vic Theatre
3145 N. Sheffield
Sheraton Sleigh Bar, Presented by Shula’s Steak House
Dec6
Festivals, Fairs & Special Events

Sheraton Sleigh Bar, Presented by Shula’s Steak House

Celebrate the holidays in Chicago at the Sheraton Sleigh Bar, presented by Shula’s Steak House—a limited-time holiday pop-up bar located inside the Sheraton Grand Chicago Riverwalk. This festive…

Saturday, December 6th
5:30 p.m.9:00 p.m.
Sheraton Grand Chicago Riverwalk
301 E. North Water Street