Oakton Street Is Turning Into Downtown Skokie's Restaurant Row, One Storefront at a Time

Backlot Bash wrapped up Sunday night, which means the three blocks of Oakton Street in front of Village Hall are open to traffic again for the first time since Friday. This is the 19th year the village has shut that stretch down for a weekend of carnival rides, a 5K, and a lineup that ran from Rod Tuffcurls & The Benchpress to a Santana tribute act. The festival's name is a nod to Skokie's stint as a filming backlot for Chicago's Essanay Film Manufacturing Company back when the village was still called Niles Center, and every August the same blocks get closed off in the same way they have for nearly two decades.

What's different this year is what those blocks looked like once the carnival rides came down. Anyone who walked Oakton Street for Backlot Bash passed at least three storefronts that didn't exist, or didn't serve food, a year ago. That's not a coincidence tied to festival timing. It's the tail end of a slower story that's been playing out at specific addresses since January, and it says something about how downtown Skokie actually fills in that a weekend festival calendar can't.

The Building That Sat Half-Empty for Years

The clearest example is the Highpoint at 8000 North, the mixed-use building at Lincoln Avenue and Oakton Street that anchors the middle of downtown. It finished construction in 2022, and part of its ground-floor retail space sat raw and unfinished for years after that, the kind of vacancy that's easy to walk past without noticing because there's no "for lease" sign screaming for attention, just blank glass.

The building now holds two restaurants. Ascione Bistro and Bar was first into the space, run by Alex Argirov and Lauren Lucchesi, who also operate a bistro of the same name in Hyde Park. The Skokie location serves handmade pastas and Lucchesi's family recipes from Southern Italy out of a 5,000-square-foot space with a 24-seat bar and a patio. Lucchesi has said they picked the location partly because it let them do something close to home for their own neighbors.

A few doors down in the same building, Amy Feldman opened Hummingbird Bowls this year. Feldman is a third-generation Skokie resident who spent six years as vice president of food sales at Lifeway Foods before deciding to build something of her own, drawing on relationships with brands like POM Wonderful and Enjoy Life Foods along the way. Getting the space at 5118 Oakton Street usable required roughly $356,000 in buildout costs, which is a real number for a raw retail shell that had been sitting untouched since the building topped out. The Skokie Village Board voted unanimously in January to help close that gap with a $45,600 grant from the village's Downtown Tax Increment Financing Rehab Program, the kind of incentive that exists specifically because finishing out a raw commercial shell costs more than most new operators expect.

"Hummingbird is the first one I'm launching as my own, and it's rooted in the place that made me."

That's Feldman's own framing for why the restaurant is where it is. But the more useful fact for anyone walking past the Highpoint this fall is that a building with a long stretch of unfinished retail space now has two full restaurants running inside it. That's not incremental turnover. That's a building catching up all at once.

The Storefront That's Been Empty the Longest Is About to Reopen

A few blocks away at 5017 Oakton Street, the space that used to hold Rich's Britches, a family-owned clothing store that closed after years downtown, is being rebuilt into Dewey's BBQ Market. The man behind it, Robert Fitzpatrick, grew up around his father's barbecue pit. Dewey Fitzpatrick Jr. ran a place called The Spare Rib outside Dallas for 53 years starting in 1951, smoking brisket and pork rib over hickory logs until he retired in 2004. Robert spent years in the Navy and then as a tech consultant in Illinois, all the while selling his father's barbecue sauce online, before deciding to open a permanent location. A former fraternity brother who now sits on the Village Board encouraged him to look at Skokie specifically.

The buildout is backed by a Retail Enhancement Program grant from the village, the same kind of tool that helped get Hummingbird Bowls off the ground a few blocks over. When it opens this fall, the space will hold a 70-seat dine-in restaurant plus a 30-seat waiting area built around deli-style service, where customers order meat by the pound the way barbecue markets have worked in northeast Texas for generations. The menu runs brisket, sliced pork, smoked ham, hot links, Polish sausage, chopped beef, and rotisserie chicken, with sides like fried okra and desserts including sweet potato and pecan pie.

What makes this worth tracking isn't just the menu. It's that downtown Skokie now has two different village-backed rehab grants funding two different restaurant buildouts inside two different long-vacant storefronts in the same calendar year, on the same street, within walking distance of each other. That's a specific and repeatable pattern, not a lucky run of unrelated openings.

The Rest of the Village Is Filling In Too

Not everything new is happening on Oakton Street itself. Over on Dempster Street, Redhot Ranch, a Chicago-style burger and hot dog spot with existing locations in Bucktown and Lakeview, moved into the space at 4811 Dempster that most recently held Oberweis Ice Cream and, before that, That Burger Joint. Owner Jeff Greenfield has said the Skokie location wasn't part of a planned expansion so much as an opportunity that came together quickly. It sits on the same side of the street as Kaufman's Bagel & Delicatessen, one of the longer-running names in that part of town.

Near Old Orchard Road, Caribana Island Grill opened in February inside the Hampton Inn & Suites, a 170-seat spot serving what its owner Bret Paul calls island-soul fusion. Paul grew up in Skokie and has run a handful of businesses since he was a teenager. He's said he picked the location for its access to the expressway and the mall, plus the mix of people who live in Skokie, Evanston, and Chicago nearby. It's open every day from 4 to 9 p.m.

So the pattern isn't confined to one block. It's spread across at least three separate commercial strips in the village at the same time, which means residents who used to drive toward the mall or into the city for something new now have reasons to stay closer to home no matter which part of Skokie they're in.

Here's the corridor as it stands heading into fall, in order along Oakton Street:

• Ascione Bistro and Bar — Highpoint at 8000 North, Lincoln & Oakton, Southern Italian
• Hummingbird Bowls — 5118 Oakton St, same building, acai bowls and smoothies
• Dewey's BBQ Market — 5017 Oakton St, opening this fall, Texas barbecue

And elsewhere in the village:

• Redhot Ranch — 4811 Dempster St, Chicago-style burgers
• Caribana Island Grill — inside the Hampton Inn & Suites near Old Orchard Road, island-soul fusion

What This Means for the Rest of the Year

The Skokie Farmers' Market still runs Sundays at Village Green through early November, and this past Sunday it briefly relocated to Oakton Street in front of the library to make room for the last day of Backlot Bash. That's a small detail, but it's a useful one. Downtown Skokie's calendar and its storefronts are more tied together than they look from a distance. The same blocks that host a 19-year-old street festival are the blocks where two separate village incentive programs just financed two separate restaurant buildouts in the same year, with a third on the way this fall.

If you live here, that means the next few months are worth walking through rather than driving past. Ascione and Hummingbird Bowls are already open. Dewey's BBQ Market should be smoking its first brisket downtown sometime this fall. None of it required new construction. It just required someone deciding the empty storefronts were worth finishing.

We spend our days in these neighborhoods, tracking which storefronts fill in and why, because that's the same groundwork that goes into pricing a home correctly or knowing what a buyer is actually walking into. If you're curious what any of this means for your own property in Skokie or nearby, Chicagoland Real Estate Advisors offers a free home valuation whenever you're ready to talk.