Oak Street's Old Theater Gets a Third Restaurant, and a Members Club to Go With It

The address at 58 E. Oak St. has carried a Del Frisco's Double Eagle sign, then an Esquire by Cooper's Hawk sign, and now carries an Esquire sign again. Crain's Chicago Business counted the new restaurant as the third in less than 15 years inside the 1930s-era movie house. Each tenant filled a big room with a big idea. Cooper's Hawk has publicly discussed the reasons for its closure.

Its CEO told Crain's that tourists showed up, but that wasn't enough for a 24,000-square-foot space. The building on Oak Street is the same, and so is the block. What has changed is the plan for who fills it and how often they return.

Three tenants, one room

The sequence is short enough to lay out.

1. Del Frisco's Double Eagle Steak House, with its Esquire Champagne Room bar, occupied the former theater first.
2. Esquire by Cooper's Hawk opened there in November 2019. It had a three-story wine tower, a tasting room and rotating menus from visiting chefs, including Tom Colicchio. The pandemic closed it within months, and it reopened in March 2022.
3. Cooper's Hawk announced the closure in May 2023, and the final service was Monday, July 17, 2023. It was the chain's only restaurant in Chicago proper. Its CEO said the pandemic and rising costs contributed to the decision, and the company said the location was underperforming.

The Cooper's Hawk concept was built to give wine club members a downtown destination, and to draw the tourists among them. The visiting-chef events were designed to generate buzz. The concept paired a large room with a visitor-oriented draw.

What the second floor changes

MStreet Collective announced the new Esquire on May 29, 2026. It is a 265-seat restaurant led by founder and CEO Chris Hyndman, whose portfolio includes Kayne Prime and Virago. Hyndman said the restaurant was conceived specifically for this historic building on this prestigious block.

The first floor looks like a large steakhouse, with a wagyu program that starts in Japan and extends to Australia, New Zealand and the United States. Seafood and sushi get equal billing, with a fish-aging program and a caviar list. Retractable glass opens the dining room to Oak Street, and there are several private dining rooms. The wine tower stays as a centerpiece. The press release describes four levels holding up to 5,000 bottles, with depth in Burgundy and Bordeaux, while The Infatuation describes three stories. Whichever count is right, the room keeps the vertical wine display that Cooper's Hawk installed.

The upstairs is where the plan departs from the last tenant. The second floor holds 58 Club, a private members club overlooking the boutiques of Oak Street. Membership is by invitation from its founding members. Inside it is ŌakSho, a 12-seat omakase counter offering a 16-course format, five nights a week with two seatings a night. The omakase is $285, and availability for non-members is limited.

A membership club, private dining rooms and a reservation-only counter share a feature. Each one depends on the same guests coming back. Cooper's Hawk also had a membership, but its wine club was national and the Chicago room was meant to be the trip a member made. Here the membership sits in the building itself, on the floor above the dining room. That is how the address is being reorganized around return visits.

Crain's said in May that the restaurant was set to open later this summer. The Infatuation now lists Esquire among its fall 2026 openings, though the outlet says it has not yet visited or rated it. The restaurant's own website is the place to confirm current reservations before planning a dinner around it.

One block over, a different bet

The corner of Oak and Rush already has a new room. ARLA opened June 18 on the entire sixth floor of 15 E. Oak St., in the former Barneys New York building where Fred's once operated. It comes from the team behind Adalina Italian on Walton Street and Adalina Prime in Fulton Market, now organized as Hospitality Included. Chef and partner Soo Ahn, who earned a Michelin star at Band of Bohemia in 2019, runs a Mediterranean-Japanese kitchen built around a live-fire grill.

ARLA's draw is the view, and it does not depend on a membership. The two terraces sit above one of Chicago's busiest intersections, one looking toward Mariano Park and one over the corner itself. A dinner there works as a night out on the block. Esquire is set up so that the building is the reason to return. The two rooms sit about a block apart on the same street and make different arguments about what keeps a large restaurant full.

Together the two rooms hold 555 seats, counting Esquire's 265 and ARLA's 230 indoor and 60 terrace seats. The old Cooper's Hawk room alone held a tasting room, a full dining floor and a retail store.

The season the address gets tested

Timing matters here. Chicago's beach swimming season ended September 7, and lifeguards are off duty until next summer. The lakefront is quieter now that the summer crowds have thinned, and October brings the Chicago Marathon, the Chicago International Film Festival and Open House Chicago to the city.

A fall walk fits the block well. Start at North Avenue Beach, which has one of the city's classic skyline views, and follow the lakefront south to Oak Street Beach. From there it is a short walk west to Oak and Rush. Lincoln Park Zoo's Fall Fest, which runs through October, sits at the northern end of the same route. It is free, with ticketed rides, and its October programs include a haunted history walking tour led by Adam Selzer and a golden-hour fall color program. The zoo's calendar lists the current times.

Esquire arrives after the beach season with a plan that rests on the second floor and the private rooms filling with guests who come back. ARLA opened in June, so its terraces are now meeting their first cool weather.

Questions about what the new rooms on Oak and Rush mean for a Gold Coast building you own or manage? Rhonda Hoff of Jameson Sotheby's International Realty follows these openings block by block and is glad to talk them through. Let's Connect.