"Black hole" is what Ald. Daniel La Spata called the vacant CVS at the Armitage end of Milwaukee Avenue in September 2021. In Block Club Chicago's report that month, he also said what neighbors kept asking him about the site: "When I was running [for office], probably every third door the question was: What can we do to bring a grocery store to this location?"
Five years later the question has an answer. Trader Joe's has a lease at 2053 N. Milwaukee Ave. Palmer Square is often described as a pocket of Logan Square bounded by Fullerton, Armitage, Kedzie and Milwaukee, which puts this building on the neighborhood's southeastern edge.
Demand at this corner was never in doubt. Paperwork has been the obstacle all along, first a lease that outlasted the store and now a list of permits and filings. Each step of that paperwork is public, so anyone can follow the store's progress without waiting for a press release.
Nine years, three grocers
The building's story since the pharmacy left goes like this:
- 2007 to 2017: A CVS operates at the site.
- 2017: CVS closes the Milwaukee Avenue store to focus on its nearby locations at 2434 N. Sacramento Ave. and 2656 N. Elston Ave.
- September 2021: Farmer's Best Market, an independent grocer with stores in the Brickyard Mall and suburban Northlake, says it is "90 percent sure" of a deal and hopes to open by the following spring. The deal later falls through.
- Early 2024: The property sells for $10.5 million. The buyer is later identified as James "Jimmy" Dremonas, owner of the Pete's Fresh Market chain. A Pete's store was rumored for the site but never opened.
- July 2024: City Council approves a special zoning district along an 11-mile stretch of Milwaukee Avenue, and the city-led plan names this building as ripe for redevelopment.
- February 2026: La Spata says Trader Joe's lease is "fully executed."
- September 2026: An ordinance passes allowing the building to be split into two retail spaces.
- October 2026: La Spata says the store is aiming for an early 2027 opening.
Before Trader Joe's, two grocery stores were linked to this site. One was an announced deal that collapsed, and the other was a rumor that never turned into a store. The deal that collapsed tells you the most.
The lease that outlasted the store
When Farmer's Best was negotiating in 2021, CVS had already been gone for four years but still held the lease for several more. La Spata explained the problem to Block Club at the time: "If you're going to start a business of this scale, you're hoping to be there for the longterm. An eight-year sublease can make it hard to justify the level of investment it takes to get a space like this up and running."
Grocery stores spend heavily on refrigeration, build-out and fixtures before they make any money. Farmer's Best planned to redo the building inside and out, glass facade included. That spending only makes sense if the store can stay long enough to earn it back. Block Club's reporting doesn't say the lease is why the deal died, but it was the stated sticking point while talks were underway.
What changed is who controls the property. A grocery operator now owns the building and is leasing the storefront to Trader Joe's, according to La Spata. The September ordinance creates a second space, about 12,000 square feet, that is being marketed to another retail tenant. That second tenant hasn't been announced.
Meanwhile the demand has only grown more specific. In 2021, Block Club noted that locals wanted more grocery stores, and a Trader Joe's in particular. By February 2026, La Spata told Block Club that the question he heard most while knocking on doors was "What can we do to bring a Trader Joe's to Logan Square?"
Five signals, in the order they tend to appear
The early 2027 date comes from the alderman. When Block Club checked in mid-October, a Trader Joe's spokesperson confirmed the store is still happening but had no timeline to share. Between the city's records and the company's own habits, though, there is a clear sequence to follow. Here is where each step stood in Block Club's October 14 report:
| Signal | Where it shows up | Status as of Oct. 14, 2026 |
|---|---|---|
| Exterior renovation permits | City permit database | Two filed in spring and summer, reviewed by several city agencies, not yet approved |
| Interior renovation permit | City permit database | Not yet filed |
| Liquor or packaged goods license | City Business Affairs and Consumer Protection | None pending |
| Store added to company's store list | Trader Joe's store search | Not listed |
| Hiring | Trader Joe's | Won't start until the store is listed |
The fourth row matters most. The company usually adds a store to its website three to six months before it opens, and the spokesperson said hiring doesn't begin until a store is listed. If the Milwaukee Avenue store appeared on that page this week, the company's usual window would put its opening sometime between late January and late April 2027. If the listing doesn't show up until after the new year, early 2027 gets harder to reach.
There is a point of comparison nearby. Trader Joe's planned Uptown store is already on the company's list, and the company confirmed this month that it will open next year. That store has cleared the step the Milwaukee Avenue store hasn't reached yet.
The permit rows follow their own order. The interior permit covers the build-out work, so an exterior permit approval followed by an interior filing would mean construction is close to starting. A packaged goods license application would mean the company is setting up the store's day-to-day operations, which suggests opening day is close.
What the corner will look like when it opens
The exterior permits describe how much of this stretch of Milwaukee will change. The planned work includes:
- Facade remodeling and roof work
- An upgraded parking lot with barrier curbs
- A new pedestrian connection to Milwaukee Avenue
- A new truck delivery area
Many of the city's Trader Joe's stores have little parking, and this one will be different. Plans in the property's marketing materials show more than 130 spaces. "We're going for the record of largest Trader Joe's parking lot in the city," La Spata said in February, laughing, as reported by Block Club Chicago.
The pedestrian connection matters for anyone walking over from the Palmer Square side. The building was designed around a car-oriented pharmacy lot. A direct path from the Milwaukee Avenue sidewalk changes how people on foot get in, and the people who have waited longest for this store live within walking distance.
The redesign also falls under the Milwaukee Avenue special character district the City Council passed in 2024. The district runs between Western and Ridgeway avenues and sets design guidelines for changes to existing buildings and for new construction. Its goals are to keep the corridor's character and to formalize community input. The September subdivision ordinance amends that plan to turn the building into a "strip center" with two retail spaces, and its text is available through the Chicago City Clerk's legislative portal.
The trade-off neighbors are already weighing
On Feb. 24, as she walked past the vacant building, a Logan Square neighbor stopped to photograph it and told Block Club how she felt about the trade-off a large grocery store brings to its street:
"It could get busier on the street. But other than that, I think it'll be nice. It's nice to have something within walking distance for the people that are local."
Both halves of that quote describe this corner. A lot with 130-plus spaces and a new truck delivery area will bring more traffic to the Milwaukee, Western and Armitage intersection than an empty building did. The walkable store that Block Club's 2024 reporting described neighbors as anxiously waiting for is also the reason that traffic will come. The empty lot's quiet came from nine years of vacancy.
The second retail space is still open. About 12,000 square feet sits next to the grocery store, and no tenant has been announced. Block Club reported that a real estate agent representing the owner didn't reply when asked whether another tenant had been secured. Whoever takes that space will have a lot of shoppers walking past on their way to the grocery store.
For now, the clearest early sign will be a new listing on a company web page. Once the Milwaukee Avenue store shows up in the Trader Joe's store search, the three-to-six-month window starts, and hiring can begin.
If you own near Palmer Square and want to know how this corner, and the Milwaukee Avenue frontage around it, could affect the way buyers see your street, Lucyna Wrucha follows changes like this block by block. Get Access to My Private Listings, and let's talk about what's moving near you before the store opens.
