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Family-Friendly 4-Day Trip to Chicago from Madison, WI

Viewed by 74 travelers

Day 1: Travel Day to Chicago

Madison, WI to Chicago, IL on March 4, 2025

8:00 AM

Breakfast at The Tallest Tree Cafe

Start your journey with a hearty breakfast at this cozy cafe known for its family-friendly atmosphere and delicious pancakes.
USD 40, 1 hour

9:30 AM

Drive to Chicago

Enjoy the scenic drive down I-90, which takes about 2.5 hours. Celebrate your arrival with the kids by playing travel games or listening to fun songs.
USD 0, 2.5 hours

12:00 PM

Lunch at Lou Malnati's Pizzeria

Famous for its deep-dish pizza, this spot is perfect for a family meal. Their buttery crust and gooey cheese will surely please everyone.
USD 60, 1.5 hours

1:30 PM

Check-in at Hotel

Settle into your family-friendly hotel in downtown Chicago which offers amenities for toddlers, ensuring a comfortable stay.
USD 200, 1 hour

2:30 PM

Lincoln Park Zoo Visit

Spend a delightful afternoon exploring one of the oldest FREE zoos in the country, perfect for toddlers with its interactive animal exhibits.
USD 0, 2 hours

5:00 PM

Return to Hotel

Head back to the hotel for a short rest before dinner.
USD 0, 1 hour

6:00 PM

Dinner at Giordano's

Treat yourselves to another Chicago staple: stuffed deep-dish pizza at Giordano's, a restaurant that welcomes families with smiles.
USD 70, 1.5 hours

7:30 PM

Evening Stroll at the Navy Pier

Finish the day with a peaceful stroll along the Navy Pier, offering stunning views of Lake Michigan and fun rides for kids.
USD 0, 1 hour
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Day 2: Exploring Chicago Landmarks

Chicago, IL on March 5, 2025

8:00 AM

Breakfast at The Breakfast House

Indulge in a wonderful breakfast with options like omelets and waffles to kick-start your day.
USD 50, 1 hour

9:30 AM

Visit Shedd Aquarium

Explore the wonders of marine life at this interactive aquarium which is sure to fascinate your toddlers with colorful fish and playful dolphins.
USD 40, 3 hours

12:30 PM

Lunch at Cafe Aquaria

Located inside the aquarium, enjoy family-friendly menu options while watching the fish swim by through the windows.
USD 60, 1.5 hours

2:00 PM

Play at Maggie Daley Park

After lunch, let the kids burn off some energy at this park with a giant climbing wall and a whimsical playground.
USD 0, 2 hours

4:00 PM

Explore Millennium Park

Take a leisurely walk around Millennium Park where you can take fun family photos in front of 'The Bean'.
USD 0, 1 hour

5:00 PM

Return to Hotel

Head back to the hotel and enjoy some downtime before dinner.
USD 0, 1 hour

6:00 PM

Dinner at Portillo's

Savor Chicago-style hot dogs and Italian beef sandwiches at Portillo's, a hit among the little ones.
USD 60, 1.5 hours

8:00 PM

Evening at the Hotel

Spend a cozy evening at the hotel, perhaps enjoying a movie night with the family.
USD 0, 2 hours
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Day 3: More Fun in Chicago

Chicago, IL on March 6, 2025

8:00 AM

Breakfast at Wildberry Pancakes and Cafe

Known for its delicious pancakes and fresh fruit, it’s a great choice for families.
USD 50, 1 hour

9:30 AM

Visit the Field Museum

Dive into the world of dinosaurs and ancient cultures which will captivate the young minds for sure.
USD 40, 2.5 hours

12:00 PM

Lunch at The Field Bistro

Located within the museum, enjoy a stress-free meal with kid-friendly options and a view of the gardens.
USD 60, 1.5 hours

1:30 PM

Exploring the Chicago Science and Industry Museum

Engage with interactive science exhibits that make learning fun for toddlers and trend towards hands-on experiences.
USD 40, 2 hours

3:30 PM

Coffee Break at Intelligentsia Coffee

Take a break while the kids enjoy pastries at this lively coffee shop perfect for a midday recharge.
USD 25, 1 hour

4:30 PM

Return to Hotel

Head back to the hotel for some family relaxation and unwind before dinner.
USD 0, 1 hour

5:30 PM

Dinner at The Cheesecake Factory

This restaurant offers an extensive menu with options that cater to every taste, including a kid's menu that your toddlers will love.
USD 70, 1.5 hours

7:00 PM

Evening at the Hotel

Relax at the hotel, perhaps with games or a movie night to wrap up the day.
USD 0, 2 hours
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Day 4: Return to Madison

Chicago, IL to Madison, WI on March 7, 2025

8:00 AM

Breakfast at Egg Harbor Cafe

Enjoy a delightful breakfast brunch at a cozy spot with plenty of kid-friendly choices.
USD 50, 1 hour

9:30 AM

Visit the Art Institute of Chicago

Explore kid-friendly exhibits and art interactions and don't miss the famous lions at the entrance.
USD 0, 2 hours

11:30 AM

Lunch at Pizano's Pizza

Enjoy one last family-friendly meal with their Chicago-style pizza, known for its phenomenal crust and toppings.
USD 50, 1.5 hours

1:00 PM

Head Back to Madison

Start your journey back home full of wonderful memories from your Chicago adventure!
USD 0, 2.5 hours
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