Family-Friendly 5-Day Chicago Itinerary with Downtown Stay and Activities

Day 1: Arrival and Downtown Exploration

Chicago, Illinois on August 9, 2025

10:00am

Check-in at Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn offers spacious rooms for families with a convenient downtown location near public transport and Magnificent Mile shopping. The total for 4 nights is approx $2,400, fitting your budget.
USD2400, 30m

11:00am

Breakfast at Wildberry Pancakes and Cafe

A family-friendly spot with extensive breakfast menu including pancakes and healthy options, located near (130 E Randolph St). Open from 7am to 2:30pm.
USD15 per person approx, 1h

12:30pm

Visit Millennium Park

Explore Millennium Park’s Cloud Gate (The Bean), Crown Fountain and open spaces, perfect for walking and photos, free entry. Open all day.
Free, 1h30m

2:30pm

Shedd Aquarium

Discover marine life at one of the largest indoor aquariums globally, fascinating for all ages. Open 9am–6pm. Tickets approx $40/adult, $30/child (3-11).
USD200 for 4 adults and 2 children approx, 2h

5:00pm

Dinner at Giordano’s

Enjoy Chicago’s famous deep-dish pizza at Giordano’s near downtown, a casual family-friendly spot, open until 11pm.
USD20-25 per pizza, 1h
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Day 2: Museum and Park Day

Chicago, Illinois on August 10, 2025

8:00am

Breakfast at Beatrix

Trendy all-day cafe with good breakfast options and healthy eats. Located at 519 N Clark St, opens 7am.
USD15 per person approx, 1h

9:30am

Field Museum of Natural History

Explore fascinating exhibits on dinosaurs, ancient civilizations, and natural science. Open 9am–5pm. Tickets approx $26/adult, $19/child.
USD126 total approx, 3h

1:00pm

Lunch at Museum Cafeteria or nearby Lou Malnati's Pizzeria

Enjoy Chicago-style pizza or quick meals inside or near the museum.
USD15–20 per person, 1h

2:30pm

Adler Planetarium

Interactive space and astronomy exhibits suitable for all ages, located near the Field Museum. Open 10am–4pm. Tickets approx $23/adult, $17/child.
USD124 total approx, 2h

5:00pm

Stroll along Navy Pier

Visit shops, amusement rides, and enjoy lake views. Free entry. Open until late.
Free, 1h30m

7:00pm

Dinner at Bubba Gump Shrimp Co., Navy Pier

Family-friendly seafood restaurant with fun decor and varied menu, suitable for adults and teens.
USD25–30 per person, 1h
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Day 3: Skyline and Shopping

Chicago, Illinois on August 11, 2025

7:30am

Breakfast at Yolk - Pine Street

Bright spot with creative breakfast dishes, located downtown, opens at 7am.
USD15 per person approx, 1h

9:00am

Visit Willis Tower Skydeck

Enjoy panoramic views of Chicago from the Skydeck 103 floors up with the glass ledge experience, open 9am-10pm. Tickets approx $35/adult, $25/child.
USD180 total approx, 2h

11:30am

Shopping and lunch along Magnificent Mile

Explore shops, and dine at family-friendly Tenderburger for quick tasty burgers and salads.
USD15–20 per person, 2h

2:00pm

Visit Chicago Children's Museum

Located on Navy Pier, this museum offers engaging educational exhibits with interactive fun for kids and teens. Open 10am–5pm. Tickets approx $15.
USD90 total approx, 2h

5:00pm

Relax at Maggie Daley Park

An expansive park with climbing walls, playgrounds, and beautiful gardens near Millennium Park.
Free, 1h

7:00pm

Dinner at Eataly Chicago

Italian market with multiple restaurants offering casual dinner options great for families, located at 43 E Ohio St.
USD20-30 per person, 1h30m
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Day 4: Science and Outdoors

Chicago, Illinois on August 12, 2025

8:00am

Breakfast at Do-Rite Donuts & Chicken

Popular spot for creative donuts and breakfast sandwiches, opens 7am.
USD10-15 per person, 1h

9:30am

Explore Museum of Science and Industry

One of the largest science museums in the world with interactive exhibits for all ages. Open 9:30am–4pm. Tickets approx $22/adult, $14/child.
USD108 total approx, 3h

1:00pm

Lunch at Museum Cafe or nearby eateries

Enjoy a casual lunch within museum or nearby in Hyde Park area.
USD15-20 per person, 1h

2:30pm

Visit Lincoln Park Zoo

Free, family-friendly zoo with a variety of animals and gardens, open 10am–5pm.
Free, 2h

5:00pm

Walk along Lakefront Trail

Enjoy scenic views of Lake Michigan with opportunities to relax or bike along the lakeshore path.
Free, 1h

7:00pm

Dinner at R.J. Grunts in Lincoln Park

Casual dining with a broad menu including burgers and salads suitable for families.
USD20-25 per person, 1h
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Day 5: Departure Day and Last Attractions

Chicago, Illinois on August 13, 2025

7:30am

Breakfast at Wildberry Pancakes and Cafe (repeat favorite)

Enjoy one last hearty breakfast near the hotel before checking out.
USD15 per person approx, 1h

9:00am

Visit Art Institute of Chicago

World-class art museum with collections that appeal to all ages and easy to navigate. Opens 10am–5pm. Tickets approx $25/adult, $19/child.
USD126 total approx, 2h

11:30am

Lunch at The Gage near Millennium Park

Upscale yet family-friendly gastropub with diverse menu near the park.
USD20–25 per person, 1h

1:00pm

Return to hotel, prepare for departure

Pack and check out to catch train or bus back to Michigan, using public transit or hotel shuttle.
Included in accommodation, 1h30m
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