Southtown
Business District
A genuine south Oak Park neighborhood strip — Avenue Ale House and its rooftop deck, Sen Sushi, Kettlestrings Tavern, Addis Café, Margaritas, Oak Park Bakery, Carnival Grocery, The Looking Glass bookstore, Westgate Flowers (since 1935), and the Hole in the Wall: a cherry-dipped custard stand that has been an Oak Park childhood memory for over 70 years.
District Overview
A South Oak Park Neighborhood Strip Built to Last
The Southtown Business District runs along South Oak Park Avenue between Lexington and Van Buren Streets, one block from the CTA Blue Line Oak Park stop. It is the kind of commercial strip that does not try to be anything other than what it is: a walkable neighborhood corridor where people actually live, shop, eat, and build decades-long relationships with the businesses that have been here for generations.
Avenue Ale House has been serving Oak Park for over 20 years — one of the largest and longest-running restaurant establishments in the village, with a rooftop deck and what it calls an “immensely large” beer selection. Sen Sushi Bar at 814 S. Oak Park Ave is owned by Chaidanai Chaiprasert, son of the owner of Mama Thai on Madison Street — a family culinary connection that runs deep in the Oak Park community. Kettlestrings Tavern at 800 S. Oak Park has become the neighborhood tap that the Wednesday Journal notes the district had been building toward. Addis Café at 801 S. Oak Park brings Ethiopian-inflected coffee and café fare to the corridor with some of the warmest reviews in the district.
But the business that most defines Southtown’s character is the one that has no seating, barely has a building, and has been there longer than almost everyone who visits it. The Hole in the Wall at 901½ S. Oak Park Ave — a frozen custard stand in a converted gangway between two buildings — has been serving south Oak Park for over 70 years. I used to go there as a kid. The cherry dipped cones. The annual opening day in spring, which spreads through the neighborhood “like lightning through the playgrounds.” That is what a real community business looks like.
- Hole in the Wall (901½ S Oak Park Ave) — 70+ years, seasonal, cherry dipped cones — a south Oak Park childhood tradition
- Westgate Flower Shop (841 S Oak Park Ave) — est. 1935, nearly 90 years, same family ownership 30 years
- Avenue Ale House (825 S Oak Park Ave) — 20+ years, rooftop deck, Oak Park’s largest ale selection
- The Looking Glass (823 S Oak Park Ave) — women-owned used bookstore, first editions, local artisans, 4.7 stars
- Sen Sushi (814 S Oak Park Ave) — owner is son of Mama Thai’s owner; hidden gem, great date night
- Carnival Grocery (824 S Oak Park Ave) — locally owned, fresh meats/produce/wine, knows its customers by name
Oak Park Neighborhoods
The Neighborhoods This District Serves
Southtown sits at the overlap point between two of Oak Park’s south-side neighborhoods — both of which benefit from the CTA Blue Line access and the walkable commercial strip on S. Oak Park Avenue.
Restaurants & Dining
Favorite Restaurants in Southtown
Southtown’s dining scene is compact, genuine, and built around businesses that have earned loyal followings over years of consistent quality. No destination dining imports — these are the spots that south Oak Park residents go back to week after week.
Grocery, Books, Flowers & More
Favorite Shops & Services in Southtown
The non-restaurant businesses in Southtown are among the most deeply community-rooted on any Oak Park corridor — a family grocery that has known its customers for decades, a florist in continuous operation since 1935, a used bookstore that is genuinely worth going out of your way for, and a bakery that supplies the whole corridor’s morning rhythm.
Photo: Prestige Real Estate Images
Your Local Expert
The Southtown Strip Is Where You See What a Real Neighborhood Commercial Corridor Looks Like
I grew up going to the Hole in the Wall. Cherry dipped cones, no seating, a building that is barely a building — and it has been there for over 70 years because south Oak Park families have kept it there. Westgate Flowers has been at 841 S. Oak Park Ave since 1935. Oak Park Bakery’s owner drove across town to deliver comfort pastries to a grieving family because someone asked nicely and it felt right. The Looking Glass is a used bookstore that hosts book clubs and sells first editions. Carnival Grocery knows its customers by name.
That is the texture of the Southtown corridor — and it matters for buyers in the same way that the Hemingway District’s restaurants matter: it shapes what daily life near here feels like in a way that square footage and school ratings cannot capture on their own. The blocks around Southtown sit between the CTA Blue Line and Madison Street, with price points that often represent some of the best value in the village. Let me show you what the options look like and what you would actually be living near before you make any decisions about this part of Oak Park.
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Oak Park’s Other Business Districts
Common Questions
Frequently Asked Questions:
Southtown District
What is the Southtown Business District in Oak Park?
The Southtown Business District runs along South Oak Park Avenue between Lexington and Van Buren Streets in south-central Oak Park, steps from the CTA Blue Line. It includes Avenue Ale House (20+ years, rooftop), Sen Sushi Bar, Kettlestrings Tavern, Addis Café, Margaritas, Oak Park Bakery, the Hole in the Wall custard stand (70+ years), Carnival Grocery, The Looking Glass used bookstore, and Westgate Flower & Plant Shop (est. 1935). Managed by the Southtown Merchant Association.
What is the Hole in the Wall and how long has it been in Oak Park?
The Hole in the Wall Custard Shoppe at 901½ S. Oak Park Ave is a seasonal frozen custard stand that has been a south Oak Park institution for over 70 years. The address is 901½ because the shop occupies a converted gangway between two buildings — there is no eat-in space. Known for soft-serve custard, cherry dip cones, sundaes, malts, shakes, and Dole Whip. A Nextdoor Neighborhood Favorite in 7 neighborhoods. Opening day each spring is a south-side community event. Open seasonally, noon–9pm (10pm Friday–Saturday).
What is the connection between Sen Sushi and Mama Thai?
Sen Sushi Bar at 814 S. Oak Park Avenue was opened by Oak Parker Chaidanai Chaiprasert — whose mother opened Mama Thai on Madison Street about a decade earlier. Chaiprasert partnered with chef Tony Silp, previously at Tsunami Japanese Restaurant in Chicago. Both restaurants are independently owned by the same Oak Park family and represent two different generations of culinary investment in the community. Sen Sushi is widely described as a hidden gem and a top date-night destination.
How old is Westgate Flower Shop?
Westgate Flower & Plant Shop at 841 S. Oak Park Avenue was established in 1935 — nearly 90 years in continuous operation. The same owners have run it for nearly three decades. It is award-winning (Best of The Knot) and holds consistent 5-star ratings across multiple platforms with 156+ Yelp reviews. Specializes in weddings, events, sympathy work, and everyday fresh arrangements. Mon–Sat 9am–6pm.
Is the Southtown area a good place to buy a home in Oak Park?
The Near South Side and South-of-290 neighborhoods surrounding Southtown typically offer some of Oak Park’s most accessible price points — with the same school district, park district, and village services as the rest of Oak Park. The CTA Blue Line Oak Park stop is steps from the Southtown corridor, giving residents direct rail access to the city. Scott has sold homes throughout both neighborhoods and can walk you through current options, pricing, and what you’d actually be living near.
Ready to Find Your Neighborhood?
Southtown Has the Kind of Community Character That Takes Decades to Build
A custard stand in a gangway that has been there since before your parents were born. A flower shop that opened in 1935. A bakery whose owner drives comfort food across town to a grieving family for free. A sushi bar opened by a chef whose mother runs the Thai restaurant on Madison Street. That is what a real neighborhood commercial strip looks like — and the residential blocks around it reflect that same depth. Let Scott show you what’s available near Southtown today.