Oak Street's Newest Tables Are Upstairs and Behind a Theater Marquee

The two biggest dining stories on Oak Street this year are both in rooms that were already restaurants. Arla opened in June on the top floor of the old Barneys building, in the space Fred's at Barneys once occupied. Esquire, a steakhouse still marked as coming soon, is set to open inside the Esquire Theater at 58 E. Oak, where two restaurants have already come and gone.

Both stories point the same way. The block between Michigan Avenue and Rush Street has new places to eat, but they aren't taking over the boutique storefronts at sidewalk level. They're reopening the large, unusual rooms that only a restaurant can fill: a full floor six stories up, and a 1930s movie palace.

The Sixth Floor Was Already a Dining Room

Arla opened on June 18, 2026, at 15 E. Oak Street. It takes up the entire sixth floor of the former Barneys building at the corner of Oak and Rush. Time Out described the space as an 8,500-square-foot rooftop restaurant in the former Fred's at Barneys space. For years, that room paired one of the city's best views with a shopping trip.

The menu is Mediterranean-Japanese, with sushi, live-fire cooking, and lake views. The team behind Adalina and Adalina Prime runs it, and chef-partner Soo Ahn told Time Out the two cuisines have more in common than you might expect.

If you live nearby, the history is what matters here. A dining room on the top floor at Oak and Rush is an arrangement the building had before. Arla brought it back with a new kitchen and a new menu, and nobody had to turn a street-level shop into a restaurant to do it.

A Theater on Its Third Menu

Farther down the block, the Esquire Theater shows how hard one of these big rooms can be to keep full.

Crain's Chicago Business reported on May 29, 2026, that a luxury steakhouse would open in the old Esquire Theater space. That makes it the third restaurant in less than 15 years to take over the sprawling 1930s building.

The most recent tenant is the one many neighbors will remember. Cooper's Hawk, the wine-focused chain based in Downers Grove, opened its only Chicago location there in November 2019. The goal was to give wine club members, especially visitors, a downtown home near Michigan Avenue. The restaurant brought in visiting chefs such as Tom Colicchio and Tyler Florence for events. In May 2023, the company said the location was underperforming and announced it would close. Founder and CEO Tim McEnery told Crain's that tourists did come, but not enough to support a 24,000-square-foot space. The last service was Monday, July 17, 2023.

Size is the problem the next tenant takes on. A 24,000-square-foot room is more than most Oak Street storefronts, and it has to fill seats night after night. Here is how the building has changed hands:

1. November 2019. Cooper's Hawk opens its only Chicago restaurant at 58 E. Oak.
2. May 2023. Cooper's Hawk announces it will leave, citing underperformance.
3. July 17, 2023. Final service.
4. May 29, 2026. Crain's reports a luxury steakhouse is planned for the space.
5. September 11, 2026. Eater Chicago lists Esquire as a late-fall opening.

What the New Esquire Plans to Put Inside

The new restaurant comes from M Street Collective and takes its name from the building. Eater describes it as a 265-seat, Japanese-influenced steakhouse with a wagyu program, sushi, caviar, and seafood prepared with fish-aging techniques.

One feature carries over from the last tenant. The multi-story, 5,000-bottle wine tower that stood in the space during the Esquire by Cooper's Hawk years is staying, and Eater reports the menu will also offer rare and reserve whiskies and an extensive sake list. According to Eater, the design draws on Hollywood's Golden Age, with custom lighting and sculptural pieces. A retractable glass window will look out over Oak Street. The building will also hold ŌakSho, a private club with a 12-seat omakase.

The plan suggests how the operators intend to fill the space. The building is divided into several experiences: a main dining room, a wine and spirits program built around the existing tower, and a 12-seat counter for a much smaller crowd. The building and the wine tower stay the same. What's new is how the space is split up.

The Sidewalk-Level Glass Is Still Mostly Retail

While the larger rooms change menus, the storefronts along the block have kept shifting between fashion labels. Here is what the most recent reporting shows, address by address:

The newest change on the list is a closing. NBC Chicago reported that the Tory Burch store at 45 E. Oak was closed as of September 18, 2026. It was the brand's only store in Chicago, and its website now says the location is closed. The exact last day wasn't clear. NBC pointed shoppers to the brand's suburban stores at Oak Brook Mall, Old Orchard in Skokie, and Fashion Outlets of Chicago in Rosemont. No report so far says what will replace it.

The arrivals before that were also fashion. Chicago YIMBY's January 2025 report described Bottega Veneta's new flagship at 41 E. Oak and Loewe's new-concept store at 51 E. Oak. It called the street boutique-forward, with vacancy under 10% at the time. WWD reported in June 2025 that Akris had opened a boutique at 101 E. Oak, near the Michigan Avenue end. That vacancy figure is from early 2025, and no newer Oak Street survey turned up in our research. It shows the street's footing going into this year, not a current count.

Eater's fall preview treats the restaurants as additions to the designer boutiques Oak Street already has, not replacements for them. The addresses back that up. Both 2026 restaurant arrivals went into spaces that once held restaurants. The storefront that opened up this fall belonged to a clothing brand, and the replacements reported over the past two years have also been clothing brands.

Reading "Late Fall" on the Esquire Calendar

If you've been watching the theater windows for signs of life, the timeline has already moved once. Crain's described the steakhouse in May as set to open "later this summer." Eater's June 11 summer preview listed a late-summer ETA. By the September 11 fall preview, that had changed to late fall. The restaurant's own website lists 58 East Oak Street with "Coming Soon 2026" and gives no month or day.

As of early October, no newer opening date has been published. For neighbors, that means Esquire is still on the way. Arla is the Oak Street dining room you can book today.

What This Means for the Block You Walk

Oak Street has long been where people in the Gold Coast walk past windows they may never go into. The 2026 changes add two dining rooms to that walk, in places easy to miss from the sidewalk. One is six floors above the corner of Oak and Rush. The other is behind a theater facade that has housed two restaurants before and is getting ready for a third.

The theater's history explains the slow pace. A 24,000-square-foot room needs a plan big enough to fill it. The last tenant brought national chefs and a wine club, and it closed after less than four years. The new team is betting on 265 seats, a private omakase club, and a wine tower already built into the walls.

At 45 E. Oak, a shop window is now dark, and no report so far says what comes next. If the past two years are any guide, the people watching that address are fashion brands. The street's newest restaurants are going into the big rooms upstairs and behind the marquee.

If you live in the Gold Coast and want a clear picture of how changes like these on your own block connect to your building and your plans, I'm happy to talk it through. My Chicago neighborhood page at buyandlistwithliz.com/neighborhoods/chicago is a good place to start, and you can always reach me directly. Let's Connect with Lizanne Pilot.