Logan Square's New Grocery Stores Will Show Up in City Paperwork Before They Open

In February a sign went up on the old CVS at 2053 N. Milwaukee Ave. announcing a Trader Joe's. It has since come down. The building has been vacant since 2017.

A few blocks south, the former Family Dollar at 2280 N. Milwaukee Ave. is now slated to become a small-format Whole Foods. Next door, the Dollar Tree at 2252 N. Milwaukee closed in late October. Neither grocery store has an opening date yet. Both projects are moving through a public sequence of permits, licenses and corporate listings, though, and each step can be checked. Taken together, those steps give a better read on timing than any one announcement.

Nine Years of Grocery Plans at 2053 N. Milwaukee

The old CVS has been a grocery site on paper for years. In 2021, the independent grocer Farmer's Best Market was set to take over the building, but that deal fell through, Block Club Chicago reported. In 2024, James "Jimmy" Dremonas, owner of the Pete's Fresh Market chain, bought the building for $10.5 million. A Pete's never came. Dremonas still owns the property and, according to Ald. Daniel La Spata (1st), is leasing the storefront to Trader Joe's.

In September the city passed an ordinance that lets the building be split into a "strip center" with two retail spaces. It amends the special zoning plan the city approved in 2024, which flagged this building and others along an 11-mile stretch of Milwaukee Avenue for redevelopment. Trader Joe's will take one space. The other 12,000 square feet are being marketed to a second retail tenant.

Parking is what will set this store apart. Unlike several other Trader Joe's locations in Chicago, it will have a large lot, and plans show more than 130 spaces. La Spata talked about it in February, as quoted by Block Club Chicago:

"We're going for the record of largest Trader Joe's parking lot in the city."

Down the Street, One Developer Bought Both Buildings

The Whole Foods site has a shorter history. Family Dollar closed the store at 2280 N. Milwaukee in 2023 because of building problems, after more than 25 years there, and the building has been empty since. It sits directly across from the MiCa Towers. In April, a limited liability company tied to Shapack Partners, a Fulton Market-based developer, bought the site for $5.6 million. In March, Shapack had already bought the neighboring Dollar Tree building at 2252 N. Milwaukee for $2.2 million.

That puts one company in control of two adjoining retail sites on this part of Milwaukee Avenue. Whole Foods goes into one. According to La Spata, the plan for the other, the 10,739-square-foot former Dollar Tree, is to divide it among new businesses. Shapack worked on the revamp of Fulton Market's retail district, which gives some idea of the kind of tenants a subdivided building might attract.

The store itself will be one of Whole Foods' smaller "Daily Shop" locations. In May, the company announced the format for Chicago, Boston and Philadelphia over the next two years, aimed at dense neighborhoods near public transit. A Wicker Park store is also in the works in the former CVS at 1200 N. Ashland Ave. La Spata explained the location in a text message to Block Club Chicago: "The opportunity to step off the train and into a grocery store is a great one for our residents."

Where Each Site Stands This Month

The Whole Foods building is a little further along physically than the paperwork shows. A permit issued in April covered a new brick facade and roof upgrades, and crews were working there over the summer. The two October filings cover a further roof replacement and a renovation with new facade openings, interior remodeling and landscaping outside.

The Filings That Come Before Opening Day

La Spata says Trader Joe's is aiming for early 2027. The company has confirmed the store is still happening. Before a ribbon-cutting, though, several things still have to happen, and each one is public:

1. Exterior permits approved. The two applications filed in spring and summer cover facade remodeling, roof work, an upgraded parking lot, barrier curbs, a pedestrian connection to Milwaukee Avenue and a new truck delivery area. They have been through several city agency reviews.
2. Interior renovation permit filed. As of mid-October, none had been filed.
3. Liquor or packaged goods license. According to the city's Business Affairs and Consumer Protection Department, none was pending for the address in mid-October.
4. The store appears on the company's store list. Trader Joe's typically adds new stores to its store search page three to six months before they open.
5. Hiring begins. A company spokesperson said hiring does not start until a store is on that list.

Step four is the one to watch. In mid-October, two other Chicago stores, Uptown and North Park, were already on the company's list, and Logan Square was not. Because a listing usually comes three to six months ahead of opening, an early-2027 opening would need the Logan Square store to show up on that page within the next few weeks. Once it does, it's fair to start planning around a date. Until then, early 2027 is a target.

The Whole Foods follows a similar path, beginning with approval of the two October permits. Both owners have one practical advantage over the last decade of grocery proposals at the old CVS: each building is already bought, and for each a grocery tenant is either signed or confirmed.

Saturdays at 2800 N. Milwaukee Until Then

The neighborhood's most reliable source of fresh food this winter is up Milwaukee Avenue from both construction sites. The Logan Square Farmers Market ended its outdoor season on Oct. 25 after Sundays at 2620 N. Milwaukee Ave. Its indoor season runs from Nov. 28, 2026, through March 27, 2027, on Saturdays from 10 a.m. to 2 p.m. on the first floor of Avondale Collective, 2800 N. Milwaukee Ave. The market's website notes that it is open on holidays, so it stays on the schedule through Thanksgiving weekend and the December holidays.

That makes two schedule changes from the warm-weather market. It moves from Sunday to Saturday, and from 8:30 a.m. to 10 a.m. This is the market's second winter at Avondale Collective. The Logan Square Chamber of Commerce listed the same Saturday 10-to-2 hours there starting Nov. 29, 2025. The winter before that, the indoor market came back after a two-year break and ran Saturdays from 9 a.m. to 1 p.m. at Breakfast for Dinner, 2537 N. Pulaski Road, as Block Club Chicago reported at the time.

Last winter's food stops included Zeitlin's Delicatessen and Kikwetu Coffee, along with vendors selling fresh meat and eggs, according to a Block Club Chicago weekend guide from January. The vendor lineup can change from season to season. The market's vendor app shows who is selling, and it's worth checking before Nov. 28.

Trader Joe's appearing on its own store list is likely to be the first clear sign that either grocery building is close to opening.

When the new stores on Milwaukee Avenue start affecting how people want to live nearby, whether that means a condo near the California Blue Line or a home within walking distance of a Saturday market, Fogel Slate Group can show you how that block compares with the rest of Logan Square. Schedule a consultation and we'll go through it with you.