January and February are traditionally slow months for Chicago restaurants. Cold weather, post-holiday budgets and Dry January can empty dining rooms across the city. In Old Town this winter, however, Wednesday nights have taken on new life thanks to a neighborhood-wide experiment: Progressive Dinner Wednesdays.
Running weekly through the end of February, the event invites diners to hop from restaurant to restaurant, sampling $5 food specials at participating Old Town establishments between 5 and 8 p.m. Organizers said the idea is simple, and intentionally affordable, encouraging guests to build their own multicourse meal down Wells Street.
Restaurants included in the promotion are Benchmark, Cal’s Corner, Declan’s Irish Pub, Fireplace Inn, Glunz Tavern, Happy Camper, Kamehachi, Moon Star Kitchen & Bar, Old Town Pub, Orso’s, Rabbit Hole, The VIG, Winnie’s, Woodie’s Flat and The Scout.
Priyanka Acharya, 23, opted to start the night at Moon Star Kitchen & Bar with her friends for appetizers. As a group, they ordered two flatbreads, one topped with kale, Parmesan and truffle, and the other with pear, whipped feta and caramelized onions. Each were $5.
“That’s really cheap for all of us,” Acharya said. “We’re kind of just looking at this as a way of exploring a new area, exploring new restaurants.”
The program is run by the Old Town Merchants & Residents Association, which serves as both a chamber of commerce and community development organization. Executive Director Marcy Huttas said the concept was born out of inspiration from a friend who lives near Estes Park, Colorado, where a similar restaurant special is held.
A diner reaches for a slice of flatbread with kale, Parmesan and truffle at Moon Star Kitchen & Bar at 1617 N. Wells St., Chicago, as part of the $5 Old Town Progressive Dinner event on Feb. 4, 2026. (John J. Kim/Chicago Tribune)
“This has been a particularly cold winter, so we wanted to do something to get people outside, support local restaurants and give residents a special reason to come out,” Huttas said.
Each participating restaurant offers a $5 course or specialty item, with menus rotating weekly. Every Saturday, OTMRA publishes a list of each restaurant’s offerings for the following Wednesday on social media and on their website.
Huttas said feedback from both diners and business owners has been overwhelmingly positive, with participation growing week to week as word spreads.
For lesser-known restaurants, the progressive dinner has served as a visibility boost during an otherwise challenging season. Moon Star, which opened in August, has seen some of its busiest nights thanks to the event.
“The progressive dinner has been really good for our new business,” said Halle Grotewold, the restaurant’s general manager. “We’ve seen college-age kids, parents with kids — demographics we don’t usually get.”
Two weeks ago, the upscale restaurant and bar served wagyu cheeseburger sliders. According to Grotewold, every table and bar seat was filled with people ordering multiple rounds of the normally $25 dish.
“Some people are on a mission to hit multiple spots, and others just come in to hang out. That’s exactly what this is for,” Grotewold said.
At Declan’s Irish Pub, owner Dave Miller admitted he was initially unsure how much traction the promotion would get.
“You never know how these things are going to go,” Miller said. “But it’s been above and beyond what we thought — 100% success for us, we love it.”
Server Megan Johns balances plates of chicken Caesar wraps at Declan’s Irish Pub as part of the $5 Old Town Progressive Dinner event on Feb. 4, 2026, in Chicago. (John J. Kim/Chicago Tribune)
Declan’s has featured rotating $5 entrées and large plates, including chicken nachos, wraps and burgers that normally cost $16 or $17. Other restaurants serving generous portions include Old Town Pub, which featured personal pizzas (regularly $15-$19) throughout January, and the Rabbit Hole, which has consistently offered a smashburger that isn’t on their regular menu.
“A $5 item is a little unusual in this day and age with food costs so high,” Miller said. “It gets people in, lets them see what we do well and hopefully brings them back.”
Miller has noticed that many diners are following the intended model, stopping at several locations in one night.
As part of the promotion, customers can request a punch card at any participating restaurant. Each $5 dish earns a punch, and once diners complete all 10 spots, they can enter a raffle for gift cards to local Old Town businesses.
Acharya’s final stop for dessert was Orso’s, a family-owned Italian restaurant and one of the oldest establishments in Old Town. For the progressive dinner, owner Agnese Milito chose to feature the house-made tiramisu, one of her longtime favorites.
“January is gray and depressing, and people are tight on money,” Milito said. “This gives them an excuse to build a little experience in Old Town, restaurant hopping instead of bar hopping.”
Diners share plates of tiramisu at Orso’s at 1401 N. Wells St., Chicago, as part of the $5 Old Town Progressive Dinner event on Feb. 4, 2026. (John J. Kim/Chicago Tribune)
Milito said the impact has been tangible.
“We’ll have 15 to 20 extra people just eating tiramisu who maybe wouldn’t have come in at all,” she said. “It keeps our servers busy, keeps the kitchen busy and gives people something fun to do until spring.”
Across the board, restaurant owners reported repeat customers and strong staff feedback. Several said it fosters a sense of community and that they would eagerly participate again if the event returns next winter.
The Old Town Progressive Dinner event runs Wednesdays through Feb. 25; more information at oldtownchicago.org.
Big screen or home stream, takeout or dine-in, Tribune writers are here to steer you toward your next great experience. Sign up for your free weekly Eat. Watch. Do. newsletter here.
https://www.chicagotribune.com/2026/02/11/old-town-wednesday-dinner-special/
