Portillo's Hot Dogs

Portillo's is not a hidden gem in the traditional sense — every Chicagoan knows it. But for visiting families, it is the single most authentic and kid-friendly Chicago food experience, and it costs half what you would spend at a sit-down restaurant. If your family eats one meal that screams Chicago, this should be it.

The Chicago-style hot dog is the essential order. An all-beef hot dog on a steamed poppy seed bun gets loaded with yellow mustard, neon green sweet relish, chopped white onion, tomato wedges, a kosher dill pickle spear, two sport peppers, and a dash of celery salt. It is a visual event — kids watch the assembly happen in front of them on the cafeteria-style line and are genuinely delighted by the neon colors and the sheer volume of toppings.

One absolute rule: do not put ketchup on a Chicago hot dog. The staff will do it if you ask, but know that this is considered a serious faux pas in Chicago food culture.

The other signature item is the Italian beef sandwich — thin-sliced, slow-roasted beef piled on a chewy Italian roll and served with sweet or hot peppers (or both). You can order it dry, wet (ladled with jus), or dipped (the entire sandwich submerged in the cooking juices). The dipped version is the most famous but also the messiest — it is essentially a sandwich that has been soaked in beef gravy.

For kids under 8, the dry version is more manageable. For teens and adventurous eaters, going dipped is the full Chicago experience.

The chocolate cake shake is the item that kids (and adults) remember longest. It is exactly what it sounds like: a thick chocolate milkshake blended with an actual slice of Portillo's chocolate cake. The result is absurdly rich, with chunks of cake throughout.

One shake is enormous — easily shareable between two kids or a parent and child. It is the kind of over-the-top indulgence that makes a vacation meal memorable.

Kid meals are a genuine value at around $7 — a hot dog or cheeseburger, fries, drink, and a cookie. Adult combo meals run $12-$15 and include a sandwich, fries, and drink. For a family of four, you are looking at roughly $40-$50 for a filling meal. Compare that to $80-$120 at any sit-down restaurant in River North, and the value is clear.

The River North location at 100 W Ontario is the most convenient for visiting families. It is walking distance from Navy Pier, Millennium Park, the Magnificent Mile, and most downtown hotels. The interior is decorated in a retro diner theme with vintage Chicago memorabilia.

The ordering system is cafeteria-style: join the line, order at the counter, pick up your food, and find a table. It looks chaotic on busy days, but the staff is fast and the line moves quickly.

One practical note: the restaurant is loud. The combination of a crowded dining room, TV screens, and the bustling kitchen creates a volume level that is actually a feature for families — no one will notice your toddler having a moment. It is casual, unpretentious, and exactly the kind of place where families with young kids can relax.