Entry No. 123 — the Chicago file — filed under: drive-in
Superdawg Drive-In
Maurie and Flaurie Berman opened this in May 1948 and put a pair of anthropomorphic hot dogs on the roof — him flexing in a leopard-print toga, her in a skirt — where they have stood ever since, still watched over by the same family. You pull into a carport, press the button on a metal speaker box, and get greeted with "Hiya, thanks for stopping. May I take your order, please?" before a carhop walks the tray out and hooks it to your window. What arrives is a Superdawg in a printed box packed tight with Superfries and a single wedge of pickled green tomato — the house drops the usual tomato slices for that, and insists on calling its relish piccalilli. It is one of the last genuinely original drive-ins left in the country, and the kitchen runs to 1 a.m. on weeknights and 2 a.m. on weekends, which makes it a dinner and a late-night both.
→ Three more weird eats & drinks in Chicago — never the same twice
The story
Maurie Berman came home from World War II, married his high school sweetheart Flaurie, and in May 1948 the two of them opened a hot dawg stand where Milwaukee, Devon and Nagle collide in Norwood Park — by the family's own account, to work their way through college. They never got around to leaving. Maurie died in 2015 and Flaurie in 2018; their son Scott Berman co-owns the place now. On the roof, two anthropomorphic hot dogs also named Maurie and Flaurie — him flexing in a leopard-print toga, her in a skirt — have stood since the opening, and they are why people who have never eaten here can describe the building.
What's there is a low stand ringed by covered carports, each with a metal speaker box. You press the button, a voice says "Hiya, thanks for stopping. May I take your order, please?", and a few minutes later a carhop hooks a tray onto your half-open window. The food comes in a printed box packed tight enough to hold its heat: a Superdawg on a poppy seed bun with mustard, piccalilli, pickle, onion and a hot pepper, a wedge of pickled green tomato standing in for tomato slices, and Superfries filling every gap. The rest of the board is aggressively trademarked — the Whoopercheesie is two Supercheesies on one bun, and the Supermalt is a full pint "so thick we put straws in them only to prove that you can't draw them through."
Almost nothing here is a revival. It is one of the few original drive-ins still operating in the country, running a 1950s ordering ritual it simply never stopped running, and the family has defended that vigorously: the trademark dates to 1984, they won a suit against a New York outfit calling itself Superdog, and in 2015 they campaigned for the hot dog emoji. A Midway Airport outpost ran from 2003 to 2010; the Wheeling stand, open since 2010, closes at 9 and has no rooftop couple.
What it's like
Turn off Milwaukee into the free lot and resist the walk-up window — take a carport, because the tray on the glass is the whole transaction. Push the button on the speaker box, order into it, then wait with the engine off; a carhop comes out with the box and hooks the tray to your window. Eat in the car with the radio low, because there is no dining room to move to. When you're finished you flip the switch on the box and someone comes back for the tray — don't drive away with it, and have cash for a tip. After 11 p.m. the carports fill with a mix of people leaving bars and people starting shifts, and the line of cars waiting to turn in off Milwaukee is the closest thing the place has to a queue.
The move: Drive up at 11 p.m. and park in a carport instead of walking to the window — the tray on the glass is the entire point. Order two Superdawgs ($9.30 each, fries included) and a Whoopercheesie to split, plus one Supermalt with two straws, and eat with the radio low. Flash the headlights when you're done so the carhop comes back for the tray, then get out and look up at Maurie and Flaurie before you pull off.
📍 Before you go 6363 N Milwaukee Ave at Devon and Nagle, on the far northwest side; open Sun–Thu 11 a.m.–1 a.m., Fri–Sat 11 a.m.–2 a.m., 773-763-0660. There's a free lot and a walk-up window, but without a car you lose the carhop service that makes it worth the trip, and there's no L stop close by. Prices run about $9.30 for a Superdawg with fries, $14.55 for the Whoopercheesie, $5.80–$7.10 for malts; any sandwich is $2.50 less without the fries. The Wheeling location at 333 S Milwaukee Ave is a different, later build and closes at 9 — go to the Chicago one.
- 📍 Chicago
- 💸 $
- ⚡ Up for anything
- 🌗 Indoors
Where: 6363 N Milwaukee Ave, Chicago, IL 60646
Hours: Added 2026-08-26 — confirm current hours before you go.
Pair it with
- Leaning Tower of Niles — It's barely a mile and a half up the road in Niles, and there is a certain logic to looking at a half-scale Leaning Tower of Pisa and a pair of rooftop hot dogs on the same night.
- Novelty Golf & Games — Two 18-hole courses of weathered fiberglass statues on Devon in Lincolnwood, open late and cash only — play first, then drive ten minutes for a tray on your window.
- Gene & Jude's — The opposite argument about the same sandwich: no seating at all, no ketchup, fries dumped straight on the dog — a twenty-minute drive southwest turns dinner into a debate.
More weird in Chicago
Good to know
Can I get there without a car?
You can — there's a walk-up window and a free lot — but there's no L stop close to 6363 N Milwaukee Ave, and without a car you skip the speaker box, the carhop and the tray, which is most of what you came for. If you're not driving, treat it as a rideshare trip out and back.
What does it cost?
About $9.30 for a Superdawg, $12.05 for a Whoopskidawg and $14.55 for a Whoopercheesie, all of which include Superfries; any sandwich is $2.50 less without them. Supermalts and Supershakes are $5.80 regular, $7.10 large. Two people eat and drink well under $30.
How late is it open?
Sun–Thu 11 a.m. to 1 a.m. and Fri–Sat 11 a.m. to 2 a.m., which makes it a legitimate late-night destination rather than just a dinner. Phone is 773-763-0660 if you want to confirm before a long drive.
Is the Wheeling location the same thing?
No. The Chicago stand at Milwaukee and Devon is the 1948 original with the rooftop figures; the Wheeling shop at 333 S Milwaukee Ave opened in 2010 and closes at 9 p.m. If you're making the trip, make it to the Chicago one.
What actually is piccalilli, and can I skip the green tomato?
Piccalilli is what the house calls its relish, and the pickled green tomato wedge takes the place of the tomato slices on a standard Chicago dog. You can ask for a Superdawg without any given trimming when you order into the box, but eat it as built the first time.
Plan a visit & invite your people →
Further reading: Official site · Wikipedia
last checked: 2026-08-26