Stores and Restaurants

Superdawg (Hot Dog) Drive-In c.1948


Gladstone Park’s retail outlets and eateries can be found up and down on the N. Milwaukee Avenue Commercial Corridor that diagonals for 2-1/4 miles straight through the middle of the community. In addition, there are pockets of one-of-a-kinds on its other major thoroughfares: N. Northwest Highway on the western border, N. Elston to the northeast, as well as a few business concerns on the eastern edge on N. Central. The beauty is that many choices are within an easy drive – or even walking distance – of most residents, enhancing the quality of life in the community.

Since the great majority of Gladstone Park businesses are modestly-sized and locally-owned, there is a distinct small town feel to the community. It’s just one of the elements that gives residents the sense of having the best of both worlds…living in a major city with access to world class culture, sports, and services, all while retaining the kind of lifestyle that comes with simpler times. It doesn’t hurt that the community, along with greater Jefferson Park of which it is a part, has for four decades maintained its status as one of the four safest of Chicago’s 77 neighborhoods. And that its 10-11 mile distance from the Loop keeps residential as well as business properties much more affordable.

But because the main commercial corridor that supports Gladstone Park’s stores, restaurants and offices developed in fits and starts much later than the rest of Chicago, it has a very distinct appearance not seen elsewhere in the city. Its unusual physical structure makes it function very differently as well.

Part of that is due to its history. Before virtually any type of shop or pub rose out of the Far Northwest’s clayey muck, the city came in and altered the look of the community for all time. Implementing the road widening recommendations of the 1909 Plan of Chicago in one of the few undeveloped areas where it still could, it expanded Gladstone Park’s 2-1/2 mile long N. Milwaukee commercial corridor to four lanes with parking on both sides, creating its boulevard look. The widened road has a profound effect on life in the community. Unlike congested areas of the city, this stretch of Milwaukee blithely handles traffic. And despite its highway-like appearance, its speed limit is deceptively slow at 35 m.p.h.

N Milwaukee's Broad Boulevard

The “broad boulevard” of N. Milwaukee that is Gladstone Park’s Commercial Corridor for all 2-1/2 miles as it runs through the middle of the community. One of the few roads in the city able to be widened to this degree based on 1909 Plan of Chicago recommendations, it has four driving lanes, a middle right/left turn lane and room for parking and bike lanes on both sides. Even though it looks like a highway, it has a posted 35 m.p.h. speed limit. Gladstonians traveling in the local community rarely encounter any traffic congestion or pedestrian road crossing problems. And since parking is so abundant both on the street and in dedicated parking lots, they do not have to put up with the parking meters so hated in the rest of the city. Photo by author.

The first wave of commercial construction in Gladstone Park occurred in the 1920s, spurred on when the 24-hour streetcar line first began operating down the full length of N. Milwaukee. Demand for goods and services came from passengers who wanted convenience as they got on or off at stops at the major crossroads in the community on the way to the big city or when returning home. Sensing opportunity, budding businessmen erected modest two-story brick buildings at those nodes following the architectural styles then popular in Chicago: a pastiche of eclectic forms ranging from neoclassicism to Art Deco. Often the small offices, stores and restaurants on their ground levels were complemented by owner apartments on their second floors. Where more people teemed, additional one-story commercial buildings were constructed to extend commerce down the street, creating the pattern of the “tall” buildings at corners with low-rise structures mid-block.

NW corner N Milwaukee-Bryn Mawr

View of the northwest corner of N. Milwaukee where it intersects with Bryn Mawr. It shows 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 two-story neoclassical yellow brick building at the left (one section altered with modern stone columns) and the one-story dark brick building with the white ceramic tile trim next to it were built between 1927 and 1931, according to the Cook County Tax Assessor’s Office, when the streetcars first starting running down N. Milwaukee making stops at major intersections like this one. The next three low-rise midcentury modern structures in the middle of the block were not built until the late 1960s during the second wave of commercial construction. 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.

Because growth throughout America was stalled by 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 undeveloped altogether.

It wasn’t until the postwar period that the second wave of commercial construction took place along the N. Milwaukee business corridor. As the community’s housing subdivisions were being built out 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. But it was not until the early 1960s that the entire Gladstone Park business district completely filled in, according to Chicago city planners who produced the Gladstone Park Corridor Study, Milwaukee Avenue from the Kennedy Expressway to the City Limits, January 28, 2017. Because of its delayed commercial growth, Gladstone Park was fortunate never to be subject to the forces of the postwar Urban Renewal movement that devalued significant historic buildings elsewhere, demolishing them to build bigger and more modern (some would say poorer) versions of themselves in its thirst for “progress.”

Low Rise Midcentury Design 2

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.

Why was Gladstone Park’s business district development always kept it at least slightly out of sync with that of the rest of the city? One factor was geography. Its location in the Far Northwest corner of Chicago was simply of greater distance from the density and purchase power of the Loop than almost any of the other 76 city neighborhoods, greatly affecting its business climate. At 10-11 miles from the center city, the community might as well have been lightyears away. While one person might rue the dampening effect the distance had on land values, another would see opportunity. With comparatively inexpensive properties, entrepreneurs during this second wave found they were able to profit even when constructing small, low-rise commercial buildings on large plots of land. Echoing the economic prosperity and optimism of the 1950s, they built sturdy, low-slung midcentury modern buildings with an abundance of windows, distinctive angular forms, bright colors and singular geometric shaped accents.

With most of the commercial corridor finally built out, business activity again slowed. The limited commercial construction there was along the Gladstone Park business district in the 1980s and 1990s followed the mall-style design that was all the rage at the time. Some six small strip malls, each with a handful of stores and shared parking lots, were built with access off N. Milwaukee. Several large banks on generous pieces of property were also erected during this time. But most of the rest of the business district stayed untouched as if frozen in time.

Stripmall 5700 block N Milwaukee at Ardmore

Strip mall with parking lot accessible from the 5900 block of N. Milwaukee at its northeast corner near W. Ardmore. Online Cook County Tax Accessor information pegs the mall with a construction date of 1988. Of the six or so strip malls built during the last two decades of the 20th Century in Gladstone Park, none have more than 10 or so units for stores, offices and restaurants, depending how they are divided up and counted. The largest strip malls anchor the southern entrance to the community near N. Milwaukee’s intersection with W. Foster and the northern end where it crosses W. Devon. The two strip malls at the north sport most of the community’s national chain stores and restaurants such as 7-Eleven, Walgreens, Subway, U.P.S., and Dunkin’/Baskin Robbins. Photo by author.

How does this come together 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 an area of 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.


Gladstone Park may not be swank, but it isn’t generic either. The few chain stores in the community tend to be clustered at either end of N. Milwaukee at the major intersections at W. Foster in the south and W. Devon in the north. Still, there are no more than a handful of branches of national corporations such as Walgreens, U.P.S., AutoZone, 7-Eleven, and Dollar General. Big box stores are nonexistent with virtually the only one anywhere nearby (a Target) in neighboring Mayfair, a half to one mile east. Residents wanting the Walmart, OfficeMax, PetSmart, Cosco, Dick’s Sporting Goods, Bed Bath & Beyond experience can drive two miles north on N. Central to find them in large strip malls on W. Touhy in suburban Skokie.

Like all communities in America affected by the growth of online stores – exacerbated first by the Great Recession of 2008 and later by the COVID-19 pandemic – Gladstone Park businesses have suffered. While service industries and restaurants have filled in some of the spaces left by some businesses going under, there are many more vacant storefronts than anyone wants. Shopping is further inhibited by the difficulty of parking in one lot and walking to several stores on one trip with merchants threatening to tow cars of customers who go off site. This is one reason why it’s so important to protect the community’s abundant street parking (and shared parking at strip malls) that alleviate such problems. Too, the commercial climate is changing as the new mode of shopping sweeping the country features small brick-and-mortars with artisan products and specialty items that need to be seen and felt to be appreciated. These are just the type of physical storefronts the community has in spades.

No self-respecting report on stores in Gladstone Park could start without first giving homage to Andy’s Deli & Mikolajczyk Sausage Shop. Other stores mentioned below are some of its other standouts, either because they have particular significance for residents or because they draw numbers of customers from outside the community.

andys deli

Andy’s Deli & Mikolajczyk Sausage Shop, 5442 N. Milwaukee, known simply by its patrons as “Andy’s,” is one of Chicago’s most renowned Polish food markets. It brings shoppers from both the center city as well as the suburbs looking for its fresh homemade traditional sausage, breads and bakery delicacies, and all sorts of spices and canned goods imported from the Homeland.

Although Andy’s presence in the community is the result of the spread of Chicago’s Polish immigrant population north toward the latter part of the 20th Century, its roots go even further back. Established by Mike Mikolajczyk in 1918, it moved to Gladstone Park in the mid-1980s after being bought by current owner Andy Kolasa. Andy’s website claims it is “the largest producer of a wide variety of authentic Polish sausages in the Chicagoland area” and as such it is highly recommended by Choose Chicago in its exploration section on the city’s Polish culture.

ben moore

Perhaps unimposing from the outside, JC Licht (Benjamin Moore) Paint, Wallpaper and Window Fashions, 5514 N. Milwaukee, draws Chicagoland customers into the Gladstone Park community from a much wider area. It’s one of the few places in the city where you can still sit at big tables and hunt through dozens upon dozens of wallpaper books and pick out that perfect print for your bedroom or kitchen after seeing and feeling it in person. It has other home design services as well.

american thermal

American Thermal Windows, 5304 N. Milwaukee, too, is singular in the Chicago area for offering a line of art glass windows that complement the city’s historic homes. The safe successor to lead-based stained glass, art glass from American Thermal comes in a variety of traditional and modern patterns. The firm also sells and installs traditional windows and doors.

H&B True Value

Residents feel particularly lucky to have the independently-owned H&B True Value Hardware Store, 5329 N. Milwaukee. Even though many local hardwares didn’t survived the era when big box stores took over, H&B has continued to do a robust business. Not only does the store have a great basic stock of everything you would expect in a hardware – and more – but also they will special order for their customers. Services include pipe, key, and glass cutting; knife, scissor and chain saw sharpening; and screen repair.

shop & save

Besides Andy’s, the regional Shop & Save functions as Gladstone Park’s main grocery store. In a strip mall at 6312 N. Nagle at the triangular intersection with N Milwaukee and W. Devon, it sports an enormous selection of fresh produce as well as products saluting the Polish population in the community, including a specialized bakery, a deli with fresh prepared dishes, and an entire aisle of authentic staples and sundries from the Homeland. Probably the most comprehensive market in the area, the Shop & Save also flies the flags…literally…of other countries above huge aisles of Mexican, Middle Eastern, Indian, and Chinese foodstuffs.

If the Shop & Save isn’t your cup of tea, you can travel four blocks east of the Gladstone community to the more epicurean Mariano’s/Kroger’s grocery store southeast at 5353 N. Elston. Only one mile south gets you to the nearest Jewel-Osco on N. Central in greater Jefferson Park. Or you can travel two miles to the nearest organic/gourmet Whole Foods Market in Sauganash.


Some people say the minute a Starbucks opens in a community, it’s gentrifying. If that’s accurate, then Gladstone Park isn’t. But it’s hardly alone in the Far Northwest of Chicago with no local Starbucks. Indeed, the much wealthier Edgebrook community to its immediate north couldn’t (or wouldn’t) support a Starbucks either. After one opened in a prime location in its commercial district, its residents continued to patronize their local coffee shops for good cups of Joe when running for the nearby train or ambling about its centralized business district. The Starbucks went out of business.

No matter. In Gladstone Park you can get coffee (and other food) at national chains such as Dunkin,’ McDonalds, Subway and 7-Eleven. You can grab a cup with your breakfast at the regional Elly’s Pancake House. Or you can have a wider choice for your caffeine fix at many more local restaurants and bakeries scattered throughout the community.

Perhaps the most popular “fast food” in Gladstone Park, like in many places, is pizza. There are no Dominoes or Little Caesars or Pizza Huts here. Instead, a number of local pizzerias too numerous to name vie for supremacy with their own versions of Chicago deep dish, New York style, stuffed, and tavern-style offerings. There are also many independent pubs interspersed throughout N. Central, N. Elston, N. Northwest Highway (as well as on N. Milwaukee) that supplement their drinks with limited to full service menus.

Gladstonians always have the option of making the two mile drive north to the Buffalo Wild Wings, Outback Steakhouse, Chili’s, and other national chain restaurants in the suburban Skokie strip malls on W. Touhy. But the best way to find an interesting and immersive dining experience is probably to do an online search for the ones “near me.” Of the 20 or so Chinese, Middle Eastern, Polish, Greek, American, Mexican, and Italian restaurants and/or bakeries in the community, several exceptional ones should be mentioned. And there was nowhere else to start than at Superdawg (Hot Dog) Drive-In Restaurant, a remnant of the carhop service from the middle of the last century.


A remnant from the days of outdoor movies and hula hoops, Superdawg (Hot Dog) Drive-In, near the corner of N. Milwaukee and W. Devon, is known nationally and internationally as one of the few remaining restaurants in America where carhops still bring food to your vehicle. Its space ship style building with its colorfully painted geometric accents and sinuous curves is vintage midcentury in both appearance and function. Topping off the spectacle are fiberglas-enforced papier-mache hotdog icons Maurie and Flaurie, named for the original owners, prancing atop the roof, their lit-up eyes flashing at night.

An anchor in the Gladstone Park community since 1948, Superdawg found its calling when it opened seasonally to summer crowds that had taken the streetcar from downtown Chicago to cool off in what later became the Whealan Pool of the Cook County Forest Preserves across the street on W. Devon. In the intervening 70 years, its carhop mode of service was always a novelty, but never became obsolete. In fact, Superdawg did screamingly well during the COVID-19 pandemic when there was no need to pivot to serve food safely since it was already socially distancing by bringing orders to customers in parked cars.

In May, 2023, Superdawg celebrated its 75th Anniversary with local politicians presenting a new honorary “Maurie and Flaurie Berman Way” street sign to hang next to the honorary “Superdawg Way” street sign. U.S. Rep. Mike Quigley entered the hot dog eatery’s anniversary in the official congressional record. The children and grandchildren of Maurie and Flaurie Berman, Northside high school sweethearts who started the restaurant after Maurie fought in the Battle of the Bulge in WWII and returned from overseas, are the current owners and operators. They noted that the kitchen is still in the original 12 x 20-foot restaurant, updated only with an electronic ordering board and intercom system. The popular Superdawg’s Chicago-style dog is exclusively sourced by a private manufacturer, served topped with mustard, relish, and onion in a poppy seed bun in a box with crinkle cut fries, a dill pickle spear and a green pickled tomato wedge.

new paradise

Gladstonians were ecstatic when New Paradise Bakery, 5742 N. Milwaukee, moved into the community in early 2022. A product of three generations of bakers from Sicily, the new shop features all varieties of pasticcini, torte, creams, and other Italian specialties including gelato. Residents regard it as a great supplement to the Polish, Greek and American bakeries already in the neighborhood.


Foodies throughout Chicagoland who want authentic Polish food come to Gladstone Park for some of the most delightful delis, bakeries, and eateries of their kind in the city. One of these that has gotten top reviews for its pierogis is SMAK-TAK, 5961 N. Elston. A full Polish experience can be had with traditional dishes supplemented by all the extras such as the 10 different types of Tymbark juices and Naleczowianka Sparkling Water imported from the homeland.

The 25% of Gladstone Park’s population that is Latino have brought their own take on food from their homelands in opening many small family-owned Mexican and Spanish restaurants in the community. There are two upscale versions.

moms old recipe

Mom’s Old Recipe, 5760 N. Milwaukee, a white tablecloth Mexican restaurant, serves a full lineup of expected and unexpected dishes from (marinated) Shrimp Ceviche to De Mole Enchiladas to Chipo Tilapia (fish with spicy garlic and chipotle served over black bean cream sauce). All is homemade and elegantly presented. The splashy murals that line the walls pave the way for late hours fun.

Cafe Marbella

Cafe Marbella, 5527 N. Milwaukee, a Spanish tapas restaurant combines ingredients in ways you never would have thought of, such as the Higo Con Tocino (stuffed figs with bacon served with brandy cream sauce) and Coca de Cebolla y Pimientos (Catalonian flatbread with caramelized onions, Spanish red peppers and manchego cheese). So many unusual cold and hot choices are available from the husband and wife who own Marbella that a vegetarian – or even a vegan – can put together a full meal here.

pasta d'arte

Two well-known Italian restaurants attract a wide clientele. The white tablecloth Pasta D’Arte Trattoria, 6311 N. Milwaukee, was recently remodeled in an eclectic New York style with medieval doors flanked by Roman-style columns in order to combine “old world Italy with modern times.” Its engaging atmosphere and extensive wine list magnifyies its Abruzzese-inspired meat dishes and Barese-influenced fish entrees.


Meanwhile, Colletti’s, 5705 N. Central at the corner of N. Elson, founded in 1946 and owned by four generations, has long been a fixture in this greater Chicago community. Locals relish eating in booths watching the Cubs, Bears, or Bulls inside the sports bar section; feasting in its large dining room; or eating outside on its large patio (igloos available for cold weather and COVID protection). Regular city folk enjoy Colletti’s as well as luminaries who come for important meetings and events that have a way of turning up on the evening news.


Perhaps the most unusual restaurant is Amitabul, 6207 N. Milwaukee, which bills its menu as Korean Spiritual Vegan Cuisine. Its name translated as “Awakening,” it opened in 1995. Attracting vegans from throughout Chicagoland who lust for its savory and healthily steamed plays on traditional Korean dishes, it avoids all animal products as well as the stir-frying oils that typically comes with them.

Besides Superdawg, two very popular American style casual restaurants in Gladstone Park are frequented for their special atmospheres.


The repurposed Garage Bar, 6154 N. Milwaukee, has an actual garage door at its storefront entrance that can be completely raised in nice weather for a fresh air dining experience. Its open rooftop section upstairs creates a fun alternate dining experience where it’s easy to get celebratory.

highway house

Highway House, 5653 N. Northwest Highway, is truly “more than just a restaurant” as it declares on its website. Distinguished by its starry lighted patio that fronts on a small side street with towering trees, the restaurant gives people the choice of dining pub style inside or al fresco style (outside) as if they’re feasting in the woods.

Consult Gladstone Park Chamber of Commerce for more resources on local businesses in the community.

The photographs below are not a comprehensive collection of Gladstone Park’s stores and restaurants. They are a selection meant to be representative of the neighborhood.

Click on a photo to enlarge and visit the gallery.