Walk north on Wells past Schiller and you'll pass a storefront that's been sitting behind paper and plywood for so long that most people in the neighborhood have stopped registering it as anything but scenery. It was Treasure Island once, the local grocery chain that closed its doors here in 2018 and never came back. Eight years is a long time for a storefront that size to sit empty on one of Old Town's busiest blocks, long enough that an entire generation of new residents moved in never having shopped there at all.
That changed at the end of August. And if you only paid attention to that one headline, you'd miss the more interesting thing happening around it: the empty grocery store isn't filling in alone. It's filling in at the exact same time three other bets are landing on the same handful of blocks, which tells you something the vacancy notice alone never could.
The Building That Waited Eight Years
The building at 1639 N. Wells has a new tenant. Whole Foods Market signed a lease there, according to a statement from 2nd Ward Ald. Brian Hopkins in his weekly newsletter at the end of August. No opening date has been set yet, but the fact that a lease exists at all closes out a stretch of vacancy that outlasted a full presidential term and then some.
Hopkins had made the site a priority for years. In his statement announcing the lease, he said restoring a full-service grocery store to this location had to be a priority. That's not empty language from a local official. Old Town has gone most of a decade relying on smaller-format grocery, delivery apps, and trips outside the neighborhood for a real weekly shop, and everyone who's lived here through that stretch knows the difference between having a supermarket down the block and not having one.
What's easy to miss in the announcement is the second sentence: Whole Foods is also planning stores in Wicker Park and Lake View. That detail matters more than it looks like it should. A single grocery chain deciding to fill one stubborn vacancy is a real estate story. The same chain deciding to open three stores across three adjacent North Side neighborhoods in the same stretch is a company betting on the whole corridor, not doing a favor for one alderman's district.
Meanwhile, the Block Filled In Around It
Wells Street didn't wait for the grocery news to start moving. FARE, the fast-casual bowl-and-coffee concept that started from a single downtown food hall counter, opened a new location this summer at 868 N. Wells, on the same stretch, tucked into the ground floor of a new luxury apartment building. The spot sits near Layla & Ringo's Cafe, DJ's Great Room, and Petite Edith, which means the block now has a run of food and coffee options standing within a few doors of each other. Founders Kasia Bednarz and Britni de Leon met working in a Chicago restaurant back in 2010 before building FARE from that first counter into a chain with locations stretching into North Carolina, and choosing Old Town for their expansion says something about where they think foot traffic is heading.
A few blocks over, SHŌ Omakase, which opened in August 2025, was named a 2026 semifinalist for the James Beard Award for Best Chef in the Great Lakes region. That's not a neighborhood consolation prize. It's a national list, and it puts a year-old Old Town restaurant in the same conversation as the best chefs working anywhere between Chicago and Minneapolis.
Put those two openings next to the grocery lease and you get three completely different kinds of businesses, at three completely different price points, making the same read on the same three blocks inside of twelve months. Fast-casual bets on volume. Fine dining bets on reputation. A national grocery chain bets on rooftops and repeat trips. When all three land in the same stretch at the same time, that's not coincidence, that's three separate underwriting processes arriving at the same conclusion independently.
The Street Closes for Its Own Party, and That's Not an Accident Either
The clearest vote of confidence, though, might come from the people who already live and work here. Old Town Oktoberfest returns to Wells Street this year, September 18 through 20, for its second run. The Old Town Merchants and Residents Association debuted the festival in 2025 and is bringing it back bigger, which is worth noticing on its own. Plenty of first-year neighborhood festivals quietly disappear after one run. This one is expanding.
Here's how the weekend breaks down:
| Day | Hours | What's new this year |
|---|---|---|
| Friday, Sept. 18 | 5 to 10 p.m. | Opening night, live German-inspired music |
| Saturday, Sept. 19 | 11 a.m. to 10 p.m. | Full Masskrugstemmen stein-holding schedule |
| Sunday, Sept. 20 | 11 a.m. to 8 p.m. | First-ever Oktoberfest Doggie Parade |
That Doggie Parade is new for 2026, with entry categories running from Wee Wieners for small breeds up to Big Bratwursts for anything over 71 pounds. A merchants' association doesn't invent a new category of programming for a festival it isn't confident will keep drawing crowds. Adding an attraction is a bet that next year's turnout beats this year's, which beats last year's inaugural run.
What Three Different Bets Add Up To
None of this reads the same in isolation. A grocery lease is a real estate footnote. A new bowl shop is a restaurant blurb. A street festival adding a dog parade is a lifestyle calendar item. But look at the timing together and the story changes: a national grocery chain, an expanding fast-casual concept, a James Beard-recognized kitchen, and the neighborhood's own merchants association all independently decided, within the same year, that Wells Street was worth expanding into rather than pulling back from.
It's worth adding one more data point from just outside the neighborhood. Old Town Pour House, the sports bar concept that started on Wells Street in 2012 with 90 beers on draft, more than any bar in Chicago carried at the time, closed its original location here in 2024. This year its parent company, Bottleneck Management, chose to bring the concept back not in Old Town but downtown in the Loop, in a building where a Google office move is reshaping the surrounding block. The Old Town name still carries enough weight to anchor a Loop restaurant deal two years after the original closed. That's a strange kind of compliment to the neighborhood that birthed it, and it says the brand equity built on these blocks travels further than the blocks themselves.
For anyone who already calls Old Town home, the practical upshot is smaller than any headline: you'll likely be doing your weekly grocery run somewhere new before long, you have another breakfast option near Schiller, and you've got a whole weekend in September where Wells Street closes to cars and opens to bratwurst and a parade of dogs in dirndls. None of that requires you to be shopping for a house. It just means the block you already live on is being bet on by more people than it was a year ago, and that's usually a sign worth filing away, whether you're renovating your kitchen this fall or just deciding where to walk the dog on a Sunday.
If you're weighing what any of this means for your own place on these blocks, whether that's timing a sale around a changing corridor or figuring out what a listing near the new Whole Foods might be worth, Jimmy Styx has been watching Old Town's blocks long enough to read the signal underneath the headlines. Reach out for a conversation grounded in what's actually happening on the street, not just what the listing photos show.
