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Holiday Club razed to make way for Uptown apartment building

Holiday Club razed to make way for Uptown apartment building

Built World Chicago, IL local

Rat Pack-themed bar closed in May after 25 years; demolition clears site for 91-unit development

October 25th, 2026: Demolition begins at Holiday Club site

Overview

Updated Oct 27

Crews have nearly finished tearing down the Holiday Club and the two buildings beside it at Sheridan Road and Irving Park Road. Developer Catapult Real Estate Solutions will put a seven-story building there with 91 apartments, about 2,000 square feet of retail and 38 parking spaces.

Renderings released in October show a revised design that reuses terra cotta from the demolished buildings on a two-story section of the east facade, after Preservation Chicago put the corner on its 2023 list of threatened buildings. Nearly 300 pallets of brick have been hauled off for reuse, and a collector pulled three pieces of original terra cotta from the rubble. The bar closed May 17 after 25 years.

Why it matters

Uptown loses a 25-year nightlife anchor and gains 91 apartments, a trade-off playing out across Chicago as housing demand rises.

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Key Indicators

91
Apartments in new building
Seven-story residential development at 4006 N. Sheridan Road replaces the Holiday Club and two adjacent buildings.
$31.5M
Reported permit construction cost
Figure carried on the caissons permit issued in April 2026; the full building permit carried a reported $23 million.
25
Years Holiday Club operated in Uptown
Opened at 4000 N. Sheridan Road in 2001; closed May 17, 2026.
38
Parking spaces in new building
Reduced from the required 91 by a Zoning Board variance approved in February 2025.
~300
Pallets of brick salvaged
Nearly 300 pallets hauled off for reuse as of late October 2026, according to Chicago YIMBY.

Voices

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People Involved

SD
Sonny Domingo
Owner of Holiday Club
Was finalizing plans in May 2026 to move Holiday Club to 3044 N. Lincoln in Lakeview; no opening confirmed since
PD
Paul Dincin
Founder, Catapult Real Estate Solutions
Leading the 4006 N. Sheridan development

Organizations Involved

Catapult Real Estate Solutions
Catapult Real Estate Solutions
Real estate development firm
Developer of the 4006 N. Sheridan Road project

Developer of the 4006 N. Sheridan Road project, a 91-unit building replacing the Holiday Club.
HC
Holiday Club
Bar / music venue
Closed May 17, 2026; building being demolished

Rat Pack-themed bar that operated at 4000 N. Sheridan Road from 2001 to 2026.
Preservation Chicago
Preservation Chicago
Preservation advocacy nonprofit
Advocated to save the buildings from demolition

Nonprofit that pushed for a preservation outcome for the Holiday Club buildings.
BF
Built Form
Architecture firm
Designer of the 4006 N. Sheridan Road building

Designed the 4006 N. Sheridan Road building with 91 units and a terra cotta-inspired facade.

Timeline

1993 October 2026

13 events Latest: October 25th, 2026 · 2 weeks ago Showing 8 of 13
Tap a bar to jump to that date

  1. Demolition begins at Holiday Club site

    Latest Construction

    The bar building is razed along with two adjacent structures to make way for the apartment complex.

  2. Redesign reuses terra cotta from demolished buildings

    Design

    Chicago YIMBY reported a revised design for 4006 N. Sheridan with a two-story section of the east facade built from terra cotta salvaged off the old buildings. Nearly 300 pallets of brick had already been hauled off for reuse.

  3. Full building permit issued

    Construction

    Chicago YIMBY reported the city issued the full permit for the seven-story, 91-unit building, with demolition permits for the three existing buildings still pending at that point.

  4. Holiday Club closes

    Closure

    The bar serves its final night after 25 years in Uptown.

  5. Holiday Club looks at a Lakeview address

    Relocation

    Uptown Update reported the bar was finalizing plans to relocate to 3044 N. Lincoln in Lakeview, a one-story building that had recently held a Waxman Candles shop.

  6. Closing date set for May 17

    Announcement

    The bar reveals its last day of service on Instagram.

  7. Caissons permit issued

    Construction

    First construction permit cleared for the 91-unit development.

  8. Holiday Club announces spring closing

    Announcement

    Owner Sonny Domingo confirms the lease ends after April and the bar will close.

  9. Zoning Board approves variances

    Regulatory

    Approval cuts required parking from 91 spaces to 38 and waives truck loading zones.

  10. Block Club reports apartment plan

    Reporting

    Details emerge of a seven-story, 91-unit building; developer hopes Holiday Club returns.

  11. Redevelopment plan announced

    Announcement

    Plans surface to turn the Holiday Club building and adjacent properties into an apartment complex.

  12. Holiday Club moves to Uptown

    Relocation

    The bar settles at 4000 N. Sheridan Road, where it operates for 25 years.

  13. Holiday Club opens in Wicker Park

    Opening

    The Rat Pack-themed bar begins in Wicker Park.

Scenarios

1

91-Unit Apartment Building Opens by 2029

Likely Resolves by End of 2029

Discussed by: Chicago YIMBY (tracking the project's permits and construction)

Demolition finishes in late 2026. Construction of the seven-story building proceeds without major delays, and units start leasing by early 2029.

2

Project Stalls or Gets Downsized

Unlikely Resolves by Q2 2028

Discussed by: Constructed as a downside risk; not actively predicted by any outlet

Construction costs rise or interest rates climb, and Catapult pauses work or revises the plan. The site could sit partially demolished while financing is renegotiated.

3

Holiday Club Reopens in a New Location

Possible Resolves by End of 2027

Discussed by: Uptown Update (reported plans for a Lakeview address in May 2026)

Owner Sonny Domingo was finalizing plans in May 2026 to move the bar to 3044 N. Lincoln in Lakeview, a one-story building that had recently housed a Waxman Candles shop, Uptown Update reported. No opening has been confirmed.

Historical Context

2 moments from history that rhyme with this story — and how they unfolded.

May 2017

Double Door closes in Wicker Park (2017)

Double Door, a legendary Chicago music venue on Milwaukee Avenue, closed after 23 years when the building was sold to a developer. Bands like The Smashing Pumpkins and Led Zeppelin's Robert Plant had played its stage.

Then

The venue's owners announced relocation plans; Double Door eventually reopened in Uptown in 2022.

Now

The closure became a symbol of how Chicago's nightlife institutions lose space to real estate development.

Why this matters now

Same city, same pattern: a beloved venue displaced by redevelopment, with the brand later seeking a new home.

October 2006

CBGB shuts its doors in New York (2006)

CBGB, the Manhattan club where the Ramones and Talking Heads got their start, closed in October 2006 after a rent dispute with its landlord, the Bowery Residents' Committee. The club had operated at 315 Bowery since 1973.

Then

The venue's final show drew hundreds; the space later became a John Varvatos store.

Now

CBGB's closure became shorthand for how gentrification pushes out cultural landmarks.

Why this matters now

Holiday Club's demolition echoes a national pattern where rising property values displace music venues that defined a neighborhood's identity.

Sources

(7)
+3
Block Club Chicago Preservation Chicago Chicago YIMBY Uptown Update Block Club Chicago Chicago YIMBY Chicago YIMBY