5 Day Chicago, South Chicago Township, Cook County, Illinois, United States Itinerary for Families (2026)

Discover the vibrant sights and eats of Chicago in this engaging 3-day itinerary tailored for families. Experience delicious food, shopping, and fun activities, ensuring an unforgettable trip for everyone.

Updated for 2026 travel. Use this itinerary as a flexible travel guide for what to do, where to go, and how to organise each day more smoothly.

5 daysmid

Chicago, South Chicago Township, Cook County, Illinois, United States itinerary overview

•Day 1: Family-friendly attractions and fun dining
•Day 2: Anime adventure and shopping delights
•Day 3: Scenic park visits and iconic sights

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Recommended area

Near South Side

Near South Side is a practical base for this itinerary with easier access to nearby stops.

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Day 1 — Family Fun

Daily est. total: ~120

Recommended area: Near South Side

Near South Side is a practical base for this itinerary with easier access to nearby stops.

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09:00 • Near South Side

🔥 Top attraction

Shedd Aquarium

Explore marine life with fascinating exhibits.

~40

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12:20 • Little Italy

Portillo's Hot Dogs

Enjoy famous Chicago-style hot dogs.

~30

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15:40 • Museum Campus

The Field Museum

Engaging exhibits for kids of all ages.

~30

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19:00 • Streeterville

Navy Pier

Family-friendly rides and lakeside views.

~20

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Day 2 — Anime & Shopping

Daily est. total: ~135

Recommended area: Schaumburg

Schaumburg is a practical base for this itinerary with easier access to nearby stops.

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09:00 • Schaumburg

Anime Central Store

Shop for anime merchandise and collectibles.

~20

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12:20 • Lakeview

Kizuki Ramen & Izakaya

Delicious ramen in a cozy setting.

~40

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15:40 • Aurora

The Chicago Premium Outlets

Great deals on popular brands.

~50

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19:00 • Arlington Heights

Mitsuwa Marketplace

Japanese grocery store with tasty food stalls.

~25

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Day 3 — Scenic Exploration

Daily est. total: ~50

Recommended area: Loop

Loop is a practical base for this itinerary with easier access to nearby stops.

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09:00 • Loop

Millennium Park

See the iconic Bean sculpture and gardens.

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12:20 • River North

Lou Malnati's Pizzeria

Famous deep-dish pizza experience.

~50

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15:40 • Lincoln Park

🔥 Top attraction

Lincoln Park Zoo

Free admission and family-friendly fun.

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19:00 • Loop

Chicago Riverwalk

Scenic walk along the river with shops.

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Day 4 — Cultural and Culinary Exploration

Daily est. total: ~75

Recommended area: Loop

Loop is a practical base for this itinerary with easier access to nearby stops.

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09:00 • Loop

The Art Institute of Chicago

A must-visit for art lovers, with stroller access.

~25

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12:20 • Chinatown

Chinatown

Explore unique shops and vibrant culture.

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15:40 • Grant Park

Buckingham Fountain

Ideal for a relaxing stroll and great photos.

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19:00 • Loop

Giordano's

Famous for deep-dish pizza, family-friendly atmosphere.

~50

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Day 5 — Science and Shopping Fun

Daily est. total: ~81

Recommended area: Hyde Park

Hyde Park is a practical base for this itinerary with easier access to nearby stops.

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09:00 • Hyde Park

Museum of Science and Industry

Interactive exhibits that kids will love.

~21

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12:20 • Loop

State Street Shopping

Explore popular shops and boutiques.

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15:40 • Loop

Grant Park

Perfect for a picnic and letting kids play.

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19:00 • South Loop

Bacon Bros. Public House

Casual dining with tasty options for all ages.

~60

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