BUSINESS DEVELOPMENT
NOTE: For a description of the wide variety of businesses currently operating in Gladstone Park, go to Business in the Community Section. At its end are many photos of representative enterprises ranging from tax offices to auto repair shops to sport gyms to banquet halls to banks. The file here speaks of the history of the development of the commercial corridor in the community from the 1920s forward.
N. MILWAUKEE COMMERCIAL CORRIDOR
As the Gladstone Park Neighborhood Association and the Gladstone Park Chamber of Commerce work to strengthening the vitality, attractiveness and resilience of its Business District in the modern era, it looks to its past to build upon. That’s because even as they’ve aided and celebrated every new concern that has opened, it’s sometimes been difficult to encourage owners of some other small-scale historic commercial buildings to improve and adapt them for new uses. Regrettably, tear downs are more and more becoming the strategy of choice.
Because Gladstone Park’s main commercial corridor developed in fits and starts much later than the rest of Chicago, it has a very distinct appearance from that of most other city neighborhoods. The combination of a super wide main street (the 4-lane N. Milwaukee Avenue) running past one- and two-story buildings gives the community its own suburban look. It makes it function very differently as well. True, there are no imposing churches or historic theaters to draw people. But there is a lot to attract visitors, whether it’s unique stores and restaurants not found elsewhere or the free parking along streets or in lots that make it easy to drive here and galavant around.
Many of the community’s differences boil down to the fact that Gladstone Park’s pattern of development was always at least slightly out of sync with the rest of Chicago. Its Far Northwest location, 10-11 miles from the Loop and lightyears away than almost any of its other 76 neighborhoods, created two special circumstances. First, because it was not yet built out so little business activity in the community at the time the city began implementing the 1909 Plan of Chicago’s road widening initiative, Gladstone Park’s 2-1/2 mile stretch of N. Milwaukee was one of the few sections of city roads that could successfully be easily expanded to the recommended four lanes with parking on both sides of the road. This altered the look of the community, distinguishing it from others, for all time.

A recently-donated photo surfaced showing the 5000 block of N. Milwaukee Avenue being widened to 4 lanes as it ran north into the Gladstone Park sub-neighborhood starting just south of W. Foster near N. Carmen Avenue (near where the 16th Jefferson Park Police Station is now located). Taken from an unspecified old daily city newspaper, the photo shows a celebration of the completed road work with banners as it achieved one of the goals of Burnham and Bennett’s 1909 Plan of Chicago. Apparently little along the roadway had to be demolished since much of N. Milwaukee had yet to be developed to any great extent. Courtesy of Nadig Newspapers and the Northwest Chicago Historical Society and reproduced at https://nadignewspapers.com/1927-photo-shows-milwaukee-avenue-shortly-after-it-was-widened-in-jefferson-park-gladstone-park-1949-photos-show-celebration-for-traffic-signals-installed-at-milwaukee-central-foster-ave/
Second, its great distance from the center city kept land values relatively low-priced in comparison, delaying the amount and type of commercial (and industrial) growth that rose of the the Far Northwest Side’s clayey muck. In fact, it wasn’t until the 24-hour streetcar line started operating down the full length of N. Milwaukee in the late 1920s that the first wave of commercial development occurred in Gladstone Park. who Passengers getting on or off at stops at the major crossroads in the community wanted the convenience to be able to pick up goods and services on the way to the big city or when returning home. Sensing opportunity, smart business owners stepped in to meet the demand. The inexpensive property further influenced the size and density of the commercial structures that were built, with entrepreneurs able to profit even when erecting relatively small two-story neoclassical/Art Deco style structures at those transportation nodes with many one-story concerns in between. Thus developed the pattern of constructing “tall” buildings where people clustered at the transportation hubs on corners where major crossroads met with lower one-story structures extending commerce down the street mid-block.
Because growth throughout America stalled during the financial devastation of the Great Depression and the disruption of WWII, few new businesses established themselves anywhere, no less in the local community during the 1930s and 1940s. The original commercial buildings on the corners where the streetcars stopped continued to loom over vacant land in the middle of blocks. Wide swaths of land not near major crossroads sat vacant during this time.
It wasn’t until the post-WWII period that the second wave of commercial construction took place along the N. Milwaukee business corridor. As the community’s housing subdivisions were going gung-ho between the late 1940s and the 1960s, the influx of new residents created more demand for services, shops, and restaurants. Business people responded, erecting storefronts and office buildings on one vacant lot after another. Even by the time the 1950s and 1960s rolled around, there were still plenty of large lots on N. Milwaukee available for new business construction, unlike most of the city that had been built out decades earlier. As commercial property continued to be very affordable, developers added to the eclectic architectural pastiche of 75-year-old commercial buildings already there with midcentury modernist structures. Echoing the economic prosperity and optimism of the 1950s, they added sturdy, low-slung midcentury modern buildings with an abundance of windows, distinctive angular forms, bright colors and singular geometric shaped accents. The Gladstone Park business district finally completely filled in.
The inexpensive land further paved the way for midcentury concerns with more square footage to spread out down on bigger pieces of property to cater to the growing postwar car culture. Less dense development on bigger pieces of property allowed business owners to welcome shoppers’ automobiles with an abundance of spaces in dedicated parking lots usually not found in other parts of Chicago…or any city. Gladstonians were given the luxury of being able to pull in and park next to larger one-story or two-story shops, restaurants, and offices and do their business freely with ease. That is, if they didn’t take advantage of the plentiful street parking that came from the increased road frontage of businesses plunked down on bigger plots of land.
During the 1980s and 1990s, the limited commercial construction was primarily in the form of several large banks on large tracts of land. Following trends of the times, some six small strip malls with a handful of stores and shared parking lots with access off N. Milwaukee also went in.
Whatever the architectural style, two-story commercial buildings often had small offices, stores and restaurants on their ground levels complemented by owner apartments on their second floors. All of these factors are what contributed to the growth of Gladstone Park’s low-rise, spread-out commercial corridor with its mom-and pop businesses. And one that looks nothing like most of the rest of Chicago.

View of 5800 block of N. Milwaukee showing the original pattern of commercial development in Gladstone Park with “tall” buildings on corners supplemented by one-story storefronts in the middle of blocks. The picture is an apt illustration of the two architectural styles 30 years and worlds apart that have long been dominant in the community. Photo by author.

A representative section of midcentury commercial buildings in the upper 5400 block of N. Milwaukee in Gladstone Park. These brick and stone buildings reflect the spare nature of “modern” architecture that eliminated unnecessary ornateness in exchange for the directness that came with the unbridled technological and scientific progress of the 1950s and 1960s. Where unaltered, there is abundant glass to express the openness and optimism of the era. The buildings’ sturdy construction and easy adaptability makes them good candidates for small offices and specialty shops in the 21st Century. Photo by author.
It wasn’t until Chicago city planners who produced the Gladstone Park Corridor Study, Milwaukee Avenue from the Kennedy Expressway to the City Limits, January 28, 2017 that the city gave much more than a sideways glance at Gladstone Park’s business district. Maybe the timing was lucky because the community suffered little effect from Urban Renewal movement of the 1960s that devalued significant historic buildings in other places, demolishing them in its thirst for “progress.” While the Far Northwest Side had no great train stations, ornate opera houses, or other significant buildings of size that could have been considered old and creaky and slated for the wrecking ball, it didn’t lose any of what it did have. Because of its staggered and delayed commercial growth and the fact it’s so far from the central city, Gladstone Park was never in a position to be so assaulted.
Ironically, old commercial buildings of the type that some real estate speculators are holding vacant and thus out of the pool of availability in hopes for an upzoned teardown may be becoming more valuable as working storefronts, as Chicago Chicago city planners pointed out. Pressure for new small restaurants with rooftop bars, for instance, as well as commercial space for specialized stores such as Herbaland, 5433 N. Milwaukee, is increasing. Gladstone Park has perfectly-sized small commercial spaces to meet the demand.
At the same time, getting Chicago to invest in new infrastructure to increase the attractiveness of the Business District has unfortunately been nearly impossible despite the city’s investment in the Corridor Study. There are no fancy brick walkways or sidewalks here. The community hasn’t even been able to get the CDOT to maintain the 14 dangerous, weedy, litter-catching planting bed bumpouts the department installed as part of the crosswalk design of its “Complete Streets” program seven years ago. They are nearly universally regarded as eyesores to nearby business owners and residents alike.
Meanwhile, vexed city officials have been known to throw up their hands over what they see as Gladstone Park’s incongruence. In some downtown enclaves the trope is that the community’s broad N. Milwaukee boulevard down the middle of the business district is more similar to the streets of Los Angeles than Chicago. The Corridor Study said so. No one quite knows for sure if this was meant as a compliment or not.
How does all this come together today, nearly a quarter of the way into the 21st Century? The traditionally low land prices combined with development on its own time schedule led to Gladstone Park’s business district assuming a most unusual presentation for a major city. With its low-rise, spread out commercial landscape, it is a duck out of water when contrasted with downtown’s tall, dense buildings or even those in Lincoln Park, Bucktown, or the North Side. And because the community’s business development occurred during two distinct waves, it was left with only two main styles of architecture. Even today, the eclectic neoclassical/Art Deco two-story business buildings from the 1920s and 1930s and the one-story midcentury modern structures of the 1950s and 1960s predominate.
As if in a time warp, many parts of the Gladstone Park business community look like they did years ago. Exteriors of original buildings, minus (perhaps) new windows and doors and perhaps signage, remain virtually unchanged as if frozen in time. While some people might lament this makes Gladstone Park a relic with commercial structures that should be put to better use, others see the opportunity to preserve the unusual nature of what the community has before it loses it.
The ultimate legacy is that Gladstone Park is one of the very few communities in Chicago with so much available parking in its commercial zones that it has never had to regulate its streets with parking meters. It may not sound like much, but to many Gladstonians, the lack of parking woes within a big city is a huge point of pride. And a big attraction to people seeking to buy homes in the community.
Today, the widened N. Milwaukee Commercial Corridor still has had a profound effect on life in the community even as it merges into and out of two other main roads (N. Elston and N. Northwest Highway). Unlike congested areas in much of the city, this stretch of the community’s main thoroughfare blithely handles vehicles with few traffic jams even if its speed limit is only 30 m.p.h. Which is one bone of contention, since passers-through often get deluded by its highway-like appearance, putting the pedal to the medal and exceeding it.
Those wanting to explore a microcosm of Gladstone Park’s two major forms of historic commercial architecture would do well to take a tour. While it’s trendy to preserve big neoclassical and Art Deco buildings from the early Twentieth Century, there isn’t nearly the level of appreciation for small midcentury commercial architecture of the 1950s and 1960s. So they should see them for themselves. Rows of 100-year-old structures along the old N. Milwaukee streetcar route are interspersed with midcentury modern buildings on both sides of the road north and south.
To view one of the community’s prime examples of postwar commercial architecture in a larger building with little exterior modification, they can explore the midcentury Habetler Bowl at 5250 N. Northwest Highway in the community’s southern end. Then they can traverse by various angular glassed storefronts of sleek design and flat roofs all the way up the main thoroughfare to find the community’s greatest cluster of Neoclassical/Art Deco-style business buildings in the blocks around N. Milwaukee’s intersection with W. Bryn Mawr. Hoofing it up to the merger of N. Milwaukee at 6145 N. Elston they will discover another rare and valuable survivor of midcentury modern design in the classic two-story Esquire Motel, built in 1959. Each room is built behind a façade of angled glass walls with classic brick and glass geometry, along with its singular signage which cycles its arrowed name in blue, red, green, and white at night. At the very end of the community near N. Milwaukee’s junction of W. Devon is a special treat: the Superdawg (Hotdog) Restaurant, 6363 N. Milwaukee, with its unique spaceship design, geometric elements, and auto stalls still served by carhops.
A few closeup shots highlighting the midcentury features of both the back of the Esquire Motel (whose angled rooms mirror the front) and the Superdawg (Hotdog) Restaurant are below. Other dozens of photos of individual commercial buildings can be accessed in the Community/Business section.

Four closeup photos illustrating some prime examples of Gladstone Park’s midcentury business architecture with its sleek and minimalist lines. Above is a back view of the Esquire Motel, which mirrors the front with each room flaunting its own angled glass wall. Below are three shots of the iconic Superdawg (Hotdog) Restaurant with its round UFO-like capped roof and diamond accents on buildings, eating areas, and auto stalls. Anyone touring the community’s commercial corridor will find themselves gaining as much of an appreciation for these 50- to 60-year-old modernist buildings where the adornment was flat roofs and geometric shapes as they have for the flourishes of its Neoclassical/Art Deco buildings that are 30 to 40 years older. It would be a shame not to try to preserve both predominant styles of business architecture currently found in the Gladstone Park business community. Photos by Mina.

After examining the community’s unique combination of commercial architecture, opinions could change, particularly in regards to the mid-century designs once so disparaged. These low-slung, sleek buildings that utilized geometric shapes and space age design expressed a period of American optimism and economic prosperity that people could easily get back to admiring today. Carol J. Dyson, Chief Architect and Deputy State Historic Preservation Officer for Illinois, has worked since 1999 particularly to promote the preservation of midcentury commercial buildings with their open-front facades and asymmetrical angles. Her Midcentury Commercial Design Evaluation and Preservation: An Opportunity for Commissioners (2017) makes a solid case for accentuating the importance of commercial buildings from the 1950s and 1960s, advising they can easily be refreshed and updated at minimal cost for 21st Century use. Like Gladstone Park’s surviving neoclassical/Art Deco commercial buildings, its modernist post-WWII construction are rare survivors and have much about them to praise. There is certainly a case for preservation for both architectural styles.