Skip to main content

Ditch the Boring Ballroom:
The Ultimate Indoor Holiday Party in Old Town

The Festive Winter Jenga Chicago Didn’t Know It Needed.
A group of women in sparkly holiday party dresses smiling and holding drinks in front of a neon sign and champagne bottles inside the indoor private event space at Utopian Tailgate in Old Town, Chicago.

Perched above Second City in Old Town

Utopian Tailgate is Chicago’s premier indoor winter playground for corporate events and holiday bashes.
Our Events Team Works Closely with Our Partners at Second City Theaters to ensure a seamless experience for groups large & small.
A high-energy, wide-angle view of a crowded indoor holiday party at Utopian Tailgate in Old Town, Chicago, featuring a massive glowing disco ball casting starry light reflections across the ceiling, vibrant neon lights, and a white Christmas tree.

Exclusive Winter Buyouts & Holiday Group Packages in Old Town:

Packages start at just $65 per person

Prime Dates & Times Book Fast!
Lock in at a discounted rate when you secure your event prior to Labor Day.

Red Garland

Utopian Winter Tailgate | The Ultimate Indoor Holiday Party HQ 

Rooftop Views | Indoor Vibes | The Iconic Second City Theaters
Professional Events for younger audiences that want to have fun and break the holiday party mold. 

When the winter weather rolls into Chicago, our vibrant indoor oasis turns up the heat. A full buyout of Utopian Tailgate gives your team exclusive private access to our immersive light setup, expansive indoor footprint, and customizable entertainment layout. From high-stakes giant game tournaments under our massive disco ball to full-scale corporate holiday galas, we provide a high-production backdrop that feels miles away from a traditional boardroom.

Send Inquiry
Event Packages
Virtual Tour
FUN WINTER
COCKTAILS

.

SECOND CITY
Group Planning Assistance

VIP Show Access

A server carrying a tray of champagne flutes during a festive corporate holiday party at Utopian Tailgate's indoor rooftop venue in Chicago.

Transform our indoor playground into your company’s private winter gala.

FULLY CUSTOM MENUS

Order from the Utopian Tailgate, Professor Pizza, or Fifty/50 Group Corporate Events Menu.

FULLY CUSTOM MENUS

Order from the Utopian Tailgate, Professor Pizza, or Fifty/50 Group Corporate Events Menu.

Early Booking Discounts

20% off Drink Packages When You Book Prior to Labor Day

Fully Customizable Space

Any Floorplan Goes

Our Staff is So Much Fun!

And we can’t wait to take care of your people.

Send Inquiry
Event Packages
Virtual Tour

Chicago Holiday Party’s Are Right Here in Old Town at Utopian Tailgate

WE PLAN THE PERFECT PARTY –
YOU GET ALL THE CREDIT

Plan an unforgettable Chicago party! Our rooftop is the perfect spot for corporate events, birthdays, and social gatherings. We offer year-round fun with team-building games like Super-sized Jenga and a vibrant indoor bar.

For a complete entertainment package, combine your rooftop party with a legendary comedy show. Our team manages both Utopian Tailgate and the theaters at The Second City, ensuring a truly seamless event for your guests.

Inquire

Our team will be in touch by the end of the business day. If received after 5:00pm, we’ll reply no later than 12pm the following business day.
Private Event Software powered by Tripleseat