Rich's Britches sold clothes on Oakton Street for decades. By this fall, the same address will smell like hickory smoke instead of new denim. That single swap, at 5017 Oakton St, is the clearest sign of something that's been building in downtown Skokie all year: a run of new restaurants landing on the same few blocks, almost all of them replacing businesses that had been there just as long.
If you live near downtown Skokie and haven't walked Oakton Street in a few months, here's what's actually different, storefront by storefront.
The Corner at Lincoln and Oakton
The building doing the most work right now is The Highpoint at 8000 North, the mixed-use building that sits right where Lincoln Avenue meets Oakton Street. It's already home to Ascione Bistro and Bar, the Italian restaurant that opened there with owners Alex Argirov and Lauren Lucchesi, who also run the original Ascione in Hyde Park. Lucchesi has said they picked Skokie in part because they wanted something close to home, a place for friends and family in the area to enjoy, and the restaurant now fills the corner with handmade pastas, a 24-seat bar and a patio in a 5,000-square-foot space.
A few doors down in the same building, at 5118 Oakton St, Hummingbird Bowls opened this year from Amy Feldman, a third-generation Skokie resident who spent more than two decades in food marketing at brands like Lifeway and POM Wonderful before deciding to build something of her own. The acai and smoothie bowl concept took real money to get open, a build-out the village itself put at roughly $356,000 for a space that had sat unfinished since the Highpoint's construction in 2022. Skokie's Village Board helped close that gap with a $45,600 grant from the Downtown Tax Increment Financing Rehab Program, the kind of public assist that rarely shows up on a restaurant's menu but explains why a raw storefront finally got finished.
So one building, two storefronts, two restaurants that didn't exist in downtown Skokie two years ago. That's not typical turnover. That's a corner being rebuilt on purpose.
What's Replacing Rich's Britches
The bigger story sits half a block away. Robert Fitzpatrick has purchased 5017 Oakton St, the longtime home of Rich's Britches, and is turning it into Dewey's BBQ Market, with an opening planned for this fall. The name comes from his father, Dewey Fitzpatrick Jr., who ran a barbecue joint 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. Fitzpatrick, who spent years in Illinois as a tech consultant after serving in the Navy, is building a custom pit modeled on his father's original design and plans a 70-seat dine-in room alongside a 30-seat area for takeout and deli-style meat sold by the pound, the old Texas barbecue-market format where you point at what you want and walk out with it wrapped in butcher paper.
The project moved forward with help from Skokie's Retail Enhancement Program, a construction grant the Village Board approved specifically for the build-out. Fitzpatrick has talked about wanting the room to carry Motown and Chicago soul on the speakers alongside the smell of hickory, and about replacing one long-running family business with another rather than watching the storefront sit empty.
That's twice now this year that a Village of Skokie grant program has quietly underwritten a new restaurant's construction costs on this same stretch of Oakton Street. It's worth knowing if you're wondering why this particular corridor is filling in faster than others nearby.
A Few More Doors Down
Keep walking and the changes don't stop at two buildings. At 4853 Oakton St, a halal concept called Sizzle is under construction, planning smash burgers, bubble tea and soft serve. Directly across the street at 4854 Oakton, Chez Lu's Extraordinary Finds opened this spring with rare and vintage collectibles, retro clothing and memorabilia, not a restaurant but part of the same block filling back in.
Around the corner on Lincoln Avenue, The Spot has taken over 7909 Lincoln Ave, a space that used to be Robert's Office Supplies and Equipment, and is building out as a rotary hot pot restaurant. It's a different cuisine and a different format than anything else on this list, which is part of the point. Downtown Skokie isn't filling in with one type of concept. It's filling in with whatever the person who bought the storefront actually wanted to open.
A little further out, the momentum shows up in different forms. Caribana Island Grill opened this year on the ground floor of the Hampton Inn & Suites at 5203 Old Orchard Road, an island-soul fusion concept from Bret Paul, who grew up in Skokie and picked the location for its access to the expressway and the mall. On Dempster Street, Redhot Ranch, known for its Chicago-style burgers at locations in Bucktown and Lakeview, has a location in the space that used to be an Oberweis Ice Cream and Dairy Store, near Kaufman's Bagel & Delicatessen. Neither is on Oakton Street itself, but both are more evidence that eating in Skokie looks different than it did a couple of years ago.
Why This Is Happening Now
None of this started in 2026. The village's own record of new business openings shows more than a dozen storefronts filled in downtown Skokie in 2024 alone, including Slyce of NY, Sweet Reserve Cafe and Bakery, Don Julio Cafe, and Botanik Culture, the flower shop that later partnered with Blue Kale on a flower-arranging workshop. In February 2025, Pickledilly Skokie opened at 4919 Main St. with 11 indoor pickleball courts in what had been vacant industrial space near Sketchbook Brewing.
What's different in 2026 is where the energy landed. Last year's openings were scattered across downtown. This year's cluster tightly on Oakton Street between Crawford and the Niles border, in storefronts that used to house other small, family-run businesses rather than sitting vacant, and with at least two of them getting a direct assist from village grant money aimed at exactly this kind of build-out.
How to Actually Walk It
If you want to see all of this in one trip, the geography makes it easy. Start at the Highpoint at Lincoln and Oakton for Ascione or Hummingbird Bowls, walk west past Sizzle and Chez Lu's, and end at 5017 Oakton once Dewey's opens later this fall. The Skokie Farmers Market runs every Sunday through early November at Village Hall, a few blocks from all of it, so a Sunday morning market run and a late lunch on Oakton line up naturally through the rest of the season.
The Downtown Skokie Merchants Collaborative also runs a guided historical walking tour through downtown, stopping at businesses and landmarks that shaped the village, pizza slice and specialty drink included. It's a strange kind of timing that a tour built around Skokie's business history now passes storefronts mid-transition, but that's where downtown is right now. If you'd rather do it without a guide, the stretch from Lincoln and Oakton to the old Rich's Britches storefront is walkable in about ten minutes.
Oakton Street changing this fast, this concentrated, tells you something about the shape of downtown Skokie right now that a drive-by wouldn't. If you're curious what that kind of storefront-level activity tends to mean for property values nearby, or you just want a straight answer from someone who tracks this corridor closely, Summerville Partners can walk you through it with a Request a Free Home Valuation.
