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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

Yesterday: Demolition begins at Holiday Club site

Overview

Updated Yesterday

The Holiday Club, the Rat Pack-themed bar that anchored Uptown nightlife for 25 years, is being demolished. A seven-story, 91-unit apartment building with ground-floor retail will replace it at 4000 N. Sheridan Road.

The project is by-right, so it needed no rezoning. It won a variance to cut parking from 91 spaces to 38. The building adds density half a block from the Sheridan Red Line stop. It also removes a 1905 structure with a 1925 Gothic terra cotta storefront that preservationists wanted saved.

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 from the caissons permit issued in April 2026; may cover all construction permits.
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.

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People Involved

Organizations Involved

Timeline

1993 October 2026

10 events Latest: Yesterday
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. Holiday Club closes

    Closure

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

  3. Closing date set for May 17

    Announcement

    The bar reveals its last day of service on Instagram.

  4. Caissons permit issued

    Construction

    First construction permit cleared for the 91-unit development.

  5. Holiday Club announces spring closing

    Announcement

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

  6. Zoning Board approves variances

    Regulatory

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

  7. Block Club reports apartment plan

    Reporting

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

  8. Redevelopment plan announced

    Announcement

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

  9. Holiday Club moves to Uptown

    Relocation

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

  10. 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 wraps up in 2027. Construction of the seven-story building proceeds without major delays, and units at the projected $1,700-$2,500 monthly rents 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: Block Club Chicago (owner Sonny Domingo said he's exploring relocation)

Domingo finds a venue in Uptown or a nearby neighborhood and reopens the Rat Pack-themed bar. This mirrors Double Door's relocation after its 2017 Wicker Park closure.

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

(4)