The one-story building at 2280 N. Milwaukee Ave. housed a Family Dollar for more than 25 years. The store closed in 2023 because of dangerous building conditions, and the building has been empty since. Less than three blocks south, the former CVS at 2053 N. Milwaukee Ave. has been empty since 2017. Several grocery proposals for it have failed over the years, including a 2021 deal with independent grocer Farmer's Best Market.
In October, both buildings got grocery news within two weeks of each other. A Trader Joe's is planned for the old CVS, and a Whole Foods is in development in the old Family Dollar. The two projects are being described in very different terms. The Whole Foods is being pitched to people who arrive on foot from the Blue Line. The Trader Joe's is being planned around its parking lot.
The Whole Foods Is Pitched to the Train
A Whole Foods spokesperson confirmed to Block Club Chicago on Oct. 27 that a store is in development at 2280 N. Milwaukee. The company shared no other details. Ald. Daniel La Spata of the 1st Ward told the outlet that it will be a smaller-format store, like the one Whole Foods confirmed earlier this year for Wicker Park. In a text message, he described it this way: "I'm excited to see more transit-oriented grocers coming to the 1st ward. The opportunity to step off the train and into a grocery store is a great one for our residents."
The smaller format La Spata is comparing it to is Whole Foods Market Daily Shop. In a May 13, 2026 announcement, Whole Foods said Daily Shop would open in Chicago, Boston and Philadelphia over the next two years. The company described the format as a "streamlined footprint" built around meals, pantry staples and grab-and-go food. Each store is meant to carry produce, meat and seafood, prepared foods, bakery items, a curated selection of 365 by Whole Foods Market products, and goods from local and regional suppliers. Whole Foods started the concept in New York City in 2024 and had eight Daily Shops at the time of the announcement, in the New York City area, Arlington, Virginia, and London. One New York location, at 1175 Third Ave., is 9,101 square feet, according to Progressive Grocer.
The only Chicago lease named in the May announcement was 1200 N. Ashland Ave. in Wicker Park. That store is going into the ground floor of the landmarked Home Bank and Trust Company Building, another former CVS, which closed in early 2023. The Logan Square store is the second Chicago Whole Foods to go into a former chain-store box in La Spata's ward this year.
The Logan Square site already has some work behind it. A building permit issued in April covered an updated brick facade and roof upgrades, and Block Club reported crews working there over the summer. The lot runs from 2274 to 2280 N. Milwaukee and includes a large parking lot next to the building, directly across Milwaukee from the MiCa Towers.
The Trader Joe's Is Pitched to the Parking Lot
The plans for the old CVS at 2053 N. Milwaukee show more than 130 parking spaces. That is a lot for a Trader Joe's in Chicago, where several stores have little or no parking. La Spata joked 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."
The building's layout explains part of it. In September, the City Council passed an ordinance allowing the property to be split into a "strip center" with two retail spaces. The ordinance amends a city plan from 2024 that named this building, along with others on an 11-mile stretch of Milwaukee Avenue, as ready for redevelopment. Trader Joe's will take one space. The other, about 12,000 square feet, is being marketed to a second retail tenant. The exterior permits also include a new pedestrian connection to Milwaukee Avenue, so foot traffic from the sidewalk is part of the plan, alongside the expanded lot.
Both sites are a few blocks from the California Blue Line station at 2211 N. California Ave. Both are at the south end of Logan Square's stretch of Milwaukee. The alderman describes one as a stop on the way home from the train and is aiming the other at people coming by car, even though the two sites are less than three blocks apart.
| 2280 N. Milwaukee Ave. | 2053 N. Milwaukee Ave. | |
|---|---|---|
| Previous tenant | Family Dollar, closed 2023 | CVS, empty since 2017 |
| Incoming grocer | Whole Foods, smaller format | Trader Joe's |
| How it's described | A "transit-oriented grocer," per La Spata | More than 130 parking spaces |
| Building work so far | Facade and roof permit issued April 2026 | Two exterior permits filed spring and summer 2026, under city review |
| Company's public timing | In development, no details shared | Confirmed, no timeline shared |
| Alderman's timing | Not given | Early 2027 target |
The Steps Before Either Store Opens Are Public
Each store has approvals and announcements to clear before it opens, and Trader Joe's has spelled out its own order of steps. A company spokesperson told Block Club that new stores go on the Trader Joe's store search page three to six months before they open, and that hiring doesn't start until a store is listed. As of mid-October, Logan Square was not on that page. The Uptown and North Park stores were, and the company said the Uptown store will open next year.
As of the Oct. 14 report, 2053 N. Milwaukee had these steps left:
- Exterior permits approved. Two applications, filed in spring and summer, had gone through several city agency reviews but were not yet approved. They cover facade remodeling, roof work, parking lot upgrades, barrier curbs, the pedestrian connection to Milwaukee, and a new truck delivery area.
- Interior renovation permit filed. No application had been submitted.
- Liquor or packaged goods license applied for. None was pending with the city's Business Affairs and Consumer Protection Department.
- Store listed on the Trader Joe's website. This is the step that starts the company's own three-to-six-month window.
- Hiring begins. The company says this comes after the website listing.
Measured against that list, an early-2027 opening would require the first four steps to happen quickly. Early 2027 is the alderman's target. Trader Joe's itself has only said the store is still happening.
The Whole Foods site has had a different kind of head start. Its shell was repaired before the company confirmed the store at all, with a new brick facade and roof upgrades permitted in April. In Wicker Park, the city issued an interior demolition permit for nonstructural partitions in the same week Whole Foods confirmed that store. Whole Foods has said opening dates for its Daily Shop locations will be announced later. An interior permit on file for 2280 N. Milwaukee would be the next sign that the Logan Square store is moving forward.
Until Then, Logan Square's Groceries Are at the North End of Milwaukee
The two new stores are at the south end of the corridor. For now, Logan Square's grocery shopping on Milwaukee is mostly near the Logan Square Blue Line station at 2620 N. Milwaukee Ave.
Dill Pickle Food Co-op is at 2746 N. Milwaukee Ave. and lists hours of 8 a.m. to 9 p.m. every day. A block north, the Logan Square Farmers Market starts its indoor winter season at Avondale Collective, 2800 N. Milwaukee Ave., on Saturday, Nov. 28. It runs 10 a.m. to 2 p.m., with more Saturdays on Dec. 5, 12 and 19, according to the Logan Square Chamber of Arts event page. Off Milwaukee, Tony's Fresh Market has a store at 3607 W. Fullerton Ave.
The farmers market has one more outdoor date before the indoor season starts. Its regular Sunday season ended Oct. 25, in the market's first season at its permanent home on the redesigned square, where more than 100 rotating farmers and food vendors set up. The last "Surplus Sunday" pop-up is Sunday, Nov. 15, from 8:30 a.m. to 2 p.m. in the Erie Family Health Center parking lot at 2418 W. Division St. in Humboldt Park. Block Club Chicago reports that parking is available across the street. After that, there's a 13-day gap before the market reopens indoors on Nov. 28.
Here's this winter's lineup along Milwaukee, from south to north:
- 2053 N. Milwaukee Ave. Former CVS, planned Trader Joe's. Exterior permits under review as of mid-October.
- 2280 N. Milwaukee Ave. Former Family Dollar, Whole Foods in development. Facade and roof work permitted in April.
- 2620 N. Milwaukee Ave. Logan Square Blue Line station.
- 2746 N. Milwaukee Ave. Dill Pickle Food Co-op, open daily.
- 2800 N. Milwaukee Ave. Avondale Collective, indoor farmers market on Saturdays starting Nov. 28.
When the two new stores open, Logan Square will have grocery shopping at both ends of Milwaukee, with the Blue Line connecting them. At the south end, the new stores will fill two buildings that have been empty since 2017 and 2023.
Openings like these affect how people value homes nearby: a short walk to a new grocer is often one of the first things buyers ask about. If you own near the south end of Milwaukee and want to know how the new stores might factor into your home's value, Vesta Preferred Realty can walk you through it. Get a Home Valuation, and we'll keep you posted as each project moves forward.
