Best Family Friendly Restaurants in Near South Side
5 hand-picked restaurants, critic-reviewed and ranked
Last Updated: February 2026
Our Top Pick
The Original Rainbow Cone
A Chicago-born cone concept serving the iconic Rainbow Cone since 1926.
Notable Picks
8.3
Vibes:
Sweet Treats Escapes
Quick Bites Champions
Family Friendly Favorites
Instagram Worthy Wonders
A Chicago legacy cone shop best known for its stacked “Rainbow Cone” slices—built for bold, old-school sweetness and fast dessert runs off Michigan Avenue. This Millennium Park outpost is most rewarding when you commit to the signature cone (or a shake built around it) and keep the rest of the order simple so the flavors stay clean and distinct.
Must-Try Dishes:
Rainbow Cone (sliced ice cream cone), Rainbow Shake, Chocolate Obsession
What Makes it Special: A Chicago-born cone concept serving the iconic Rainbow Cone since 1926.
#2
Flo & Santos
8.3
A loud, high-energy South Loop tavern where thin-crust pizza is the default and Polish comfort dishes make it easy to feed a mixed-age table. It works best when you keep the order tight: one pizza for the table plus one shared plate, then decide if anyone still needs a chicken parm or entrée.
Must-Try Dishes:
Thin-crust pizza, Pierogi, Chicken parmigiana
What Makes it Special: A pizza-first South Loop room where Italian comfort overlaps with pierogi classics.
8.3
Vibes:
Comfort Food Classics
Family Friendly Favorites
Quick Bites Champions
Solo Dining Sanctuaries
A reliable South Loop sushi house built around steady, repeatable execution—classic rolls, nigiri, and simple hot appetizers that travel well. It’s the kind of neighborhood place you use for weeknight takeout or an easy dine-in sushi run when you want consistency over spectacle.
Must-Try Dishes:
Sashimi combo, Salmon avocado roll, Gyoza
What Makes it Special: High-repeatability neighborhood sushi that’s built for both dine-in and takeout nights.
8.2
La Cantina Grill is a South Loop Mexican staple near McCormick Place, combining a full bar, broad menu, and a sizable vegan offering. It’s where locals, convention-goers, and families converge for fajitas, enchiladas, and margaritas before events or casual dinners.
Must-Try Dishes:
Traditional Enchiladas, Shrimp Fajitas, Mayan Tamales
What Makes it Special: High-volume South Loop cantina with a full bar, broad vegan-friendly menu, and flexible seating near Soldier Field and McCormick Place.
Worthy Picks
7.9
This South Loop outpost of the Chicago-based Pizano's group serves deep-dish and thin-crust pies, pastas, and salads a short walk from McCormick Place and Wintrust Arena. It’s a go-to for groups and travelers who want recognizable Chicago-style pizza with full bar service near the convention center.
Must-Try Dishes:
Rudy's Special Deep-Dish Pizza, Thin-Crust Sausage and Pepperoni, House Salad
What Makes it Special: Convention-area pizzeria offering deep-dish and thin-crust with full bar and TVs.