“If you’ve ever been to the Sky Ride Tap, you’ve undoubtedly seen Kyriakos ‘Carl’ Damianides. Since he bought the bar in 1972, he’s been a near-constant presence inside.

“‘For the first 25 years, I worked from 7 a.m. to 2 a.m., seven days a week,’ he said. Since then, Damianides has slowed down a bit. Currently, the Sky Ride, 105 W. Van Buren St., is open on weekdays, usually 10 a.m.-8 p.m., but if the doors are open, he’s there tending bar, stocking the coolers and chatting with the regulars.

“Besides the shorter hours, not much else has changed about the bar since Damianides took over. It still doesn’t take credit cards. There’s no cocktail list. Renovations have been kept to an absolute minimum. He did add floor tile in 1974, but he learned early on not to make too many changes.

“His self-proclaimed biggest mistake was putting up wood paneling back in 1978. ‘The wall was crumbling and dusty, so I put in the paneling,’ he said. ‘Immediately, I lost 50 percent of my business. The regulars felt like this was their house. And they didn’t like the change.’

“Located under the ‘L’ tracks a block from the LaSalle Street station, the Sky Ride always had a committed commuter crowd in need of a quick drink or two before the ride home. Early on, the bar also catered to the many men’s-only hotels that used to operate around the southern end of the Loop. A dedicated morning crowd would line up out front waiting for Damianides to open the doors.

“That’s changed as the hotels closed. Though the Sky Ride still draws people getting off overnight shifts, now it’s mostly an after-work spot. And more change may be on the horizon for Damianides and the bar: The Holabird & Roche-designed building it’s in, which dates to 1898, is for sale.

“The Sky Ride Tap’s history stretches back to 1933. That’s the year Chicago held its second world’s fair, the Century of Progress Exposition. As a main attraction, the planners concocted a massive aerial tramway dubbed the Sky Ride. Designed to transport visitors across the lagoon to Northerly Island, its scale was striking. To cover the 1,850-foot span, organizers constructed two massive metal towers, each 628 feet tall. Visitors took elevators up, before boarding rocket-shaped cars that traversed the span on massive cables connected to the towers.

“While the Sky Ride hasn’t changed much in the 54 years Damianides has run it, business has slowed lately, he said. The rise of people working from home since the pandemic has been especially rough.

“‘Even the ones that come down to work two or three days a week, when they get off work, they don’t stop here,’ he said. ‘People used to stop by, have a beer, and then catch the train. Friday was always the best day. Now it has become the worst.’

“The Sky Ride Tap’s building, the Yukon Building, is also facing an uncertain future. This year, Preservation Chicago included it on its ‘Chicago 7 Most Endangered’ list.

“Originally known as the Yukon Building, the two-story structure was constructed in 1898 by Holabird & Roche, a Chicago firm best known for designing local landmarks like the Marquette Building, the Old Colony Building and the southern section of the Monadnock Building.

“Preservation Chicago Executive Director Ward Miller said the building is on the endangered list because there are so many vacancies, and the entire building was recently put up for sale. He acknowledged it’s not in the best shape and needs lots of updates, but he thinks it’s worthy of landmark status.

“‘Though small, it’s a really forward-thinking building,’ said Miller. ‘In some aspects, it was 50 years ahead of its time. It has bands of windows that allow in a tremendous amount of light, and the cornice is all original.’

“Miller said the nonprofit is encouraging prospective buyers of the building to retain the Sky Ride Tap because of its legacy.” (Kindelsperger, Block Club Chicago, 7/6/26)

“The two-story Yukon Building, later renamed the Bock Building, was financed and developed by the Brooks Brothers of Boston in 1898. It was designed by Holabird & Roche. Initial plans were for a much larger building. The simplicity of the building’s design, integration of continuous glass storefronts and bands of continuous windows on the second floor make it truly modern for its era. Most likely conceived as a reasonably priced improvement of the property, the building’s iron and glass facades and bands of ribbon-windows at its second floor anticipate designs popularized decades in the future.

“The Yukon Building is considered an early example of — and oldest extant — ‘taxpayer building’ in the central area of Chicago. The term ‘taxpayer building’ describes a modest-scale structure that earned enough funds to cover the yearly tax bill and give the owners a small profit or monetary return. For many decades, these smaller structures have been repeatedly targeted for redevelopment projects across the Loop, often replaced with large office buildings or, as on Van Buren Street, multi-story parking garages.

“Originally conceived as an eight-story or a twelve-story building, the Yukon Building was designed by noted Chicago architectural firm Holabird and Roche in March of 1898. In the months that followed, published plans reflected a more modest two-story development, the building now anchoring the southwest corner of Clark and Van Buren Streets. A financial panic in the mid-to-late 1890s, along with construction of the Union Loop Elevated structure along Van Buren Street in 1897, most likely impacted the desirability of the site for a tall commercial office building.

“The project was financed by Peter Chardon Brooks III and Shepherd Brooks, known as the Brooks Brothers of Boston, who had financed a number of remarkable early Chicago steel-framed buildings that are recognized as some of the earliest skyscrapers. These innovative and remarkable buildings include Burnham & Root’s Rookery Building (1885) and Holabird & Roche’s Montauk Block (1882-1902), the Monadnock Building (1891), and the Marquette Building (1893). Several of them are published frequently in the annals of skyscraper construction and have been designated as Chicago Landmarks.

“Importantly, the Yukon Building is a survivor of Chicago’s ‘Old Chinatown,’ predating the movement of the Chinese Community and businesses further south to 22nd Street/Cermak Road and Wentworth in the 1920s.

“Several other small historic businesses have also been impacted by fallout from the Covid Pandemic and the potential sales listing of the Yukon Building, including two Chicago Legacy Businesses, Boni Vino Italian Restaurant and the Sky Ride Tap.

“Preservation Chicago is of the opinion that the Yukon Building stands as a fine and rare example of a small commission by one of Chicago’s most recognized and prolific architecture firms. The building also captures a history related to Chinese culture in an age where we are now recognizing and protecting historic Chinatowns across the nation. As the Yukon Building remains as one of the last structures of Chicago’s ‘Old Chinatown,’ before its move southward in the 1920s to the Armour Square Community, we are of the opinion that the building should be protected and given a Chicago Landmark designation, noting its architectural, historical and cultural significance to our city.” (Yukon Building, a Preservation Chicago 2026 Chicago 7 Most Endangered Chapter)

Carl Damianides is a remarkable Chicagoan, and the Sky Ride Tap is a remarkable Chicago Legacy Business. The bar has served as a neighborhood gathering place in the heart of the Loop for more than 90 years. But the bar’s fate is tied to the building that houses it, and the building’s future is genuinely uncertain.

The Yukon Building (Bock Building) has now been named to the Preservation Chicago Chicago 7 Most Endangered list twice — in 2016 under the category of “Old Chinatown,” and again in 2026.

Its remarkable iron-and-glass façade, its bands of ribbon windows, and its two-story civic modesty make it an outlier in the Loop that has only grown more distinctive as the surrounding blocks have been transformed by parking garages, federal buildings, and large institutional additions over the past half century.

Preservation Chicago is actively encouraging prospective buyers of the Yukon Building to embrace and restore its architecture and embrace and preserve its long-term tenants — specifically the Sky Ride Tap. We urge stakeholders to move forward with Chicago Landmark designation for the Yukon Building to protect this irreplaceable piece of the Loop’s commercial and cultural history.

The Sky Ride Tap holds a special place for us as we celebrated Preservation Chicago’s 21st birthday with a joyful happy hour celebration on Friday, October 21, 2022 at the Sky Ride Tap to recognize 21 years on the preservation front lines.

Read the full story at Block Club Chicago and Preservation Chicago

• Meet The Man Behind The Sky Ride Tap, The Loop’s Last Real Dive Bar; Kyriakos “Carl” Damianides has run the Sky Ride Tap since 1972. While business has slowed and the building’s future is uncertain, “I’m still healthy,” he said, Nick Kindelsperger, Block Club Chicago, 7/6/26
• The Yukon Building; a Preservation Chicago 2026 Chicago 7 Most Endangered chapter
• These Are Chicago’s Most Endangered Buildings In 2026; Block Club Chicago, 3/4/26
• Preservation Chicago’s 21st Birthday Old-School Happy Hour at the Sky Ride Tap 10/31/22
• Yukon Building at 111 W Van Buren Street Listed For Sale 
• This Time Capsule Downtown Block, Once Called Chicago’s Worst, Is ‘Run Down And Real’ — And Home To A Community; Block Club Chicago, 8/2/19