5-Day Family-Friendly Itinerary to Chicago from Madison, WI

Day 1: Travel Day

Madison, WI to Chicago, IL on March 5, 2025

8:00 AM

Depart Madison

Start your journey with a scenic drive to Chicago. Prepare snacks and games for the little ones to keep them entertained during the trip.
CURRENCY0, 2 hours

10:00 AM

Check-In at Hotel

Arrive in Chicago and check into a family-friendly hotel, such as The Drake, known for its spacious rooms and kid-friendly amenities.
CURRENCY0, 1 hour

11:00 AM

Millennium Park

Visit Millennium Park, where toddlers can enjoy the Crown Fountain and ample green space to run around.
CURRENCY0, 2 hours

1:00 PM

Lunch at The Gage

Enjoy a family-friendly lunch at The Gage, offering a kids' menu and delicious pub fare just steps from Millennium Park.
CURRENCY50, 1 hour

2:00 PM

Explore the Art Institute of Chicago

Visit the Art Institute, where children can participate in family programs and explore the Modern Wing.
CURRENCY36, 2 hours

4:30 PM

Return to Hotel and Relax

Head back to the hotel for some rest time. Let toddlers recharge before evening activities.
CURRENCY0, 1.5 hours

6:00 PM

Dinner at Giordano's

Experience deep-dish pizza at Giordano's, a Chicago favorite with kid-friendly options and a warm atmosphere.
CURRENCY60, 1.5 hours
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Day 2: Adventure Day

Chicago, IL on March 6, 2025

8:00 AM

Breakfast at Lou Mitchell's

Start your day with a hearty breakfast at Lou Mitchell's, famous for its complimentary milk duds and family-friendly environment.
CURRENCY40, 1 hour

9:30 AM

Visit Shedd Aquarium

Explore the wonders of the Shedd Aquarium, where children can interact with sea life and watch feeding shows.
CURRENCY90, 3 hours

12:30 PM

Lunch at Café 310

Have lunch at Café 310, located within the aquarium, offering quick bites and kid-friendly meals.
CURRENCY50, 1 hour

1:30 PM

Visit the Field Museum

Discover the Field Museum's dinosaur exhibits and kid-friendly educational programs that will engage your toddlers.
CURRENCY70, 2.5 hours

4:00 PM

Play at Grant Park

Let the kids run and play at Grant Park, with playgrounds and lots of space to enjoy the outdoors.
CURRENCY0, 1 hour

5:30 PM

Dinner at Pequod's Pizza

Savor some local favorites with a visit to Pequod's for its famous caramelized crust deep-dish pizza in a relaxed setting.
CURRENCY60, 1.5 hours
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Day 3: Cultural Day

Chicago, IL on March 7, 2025

8:00 AM

Breakfast at Eggy's

Enjoy a fun breakfast with delectable pancakes and creative egg dishes at Eggy's, a kid-friendly breakfast spot.
CURRENCY50, 1 hour

9:30 AM

Visit Lincoln Park Zoo

Explore Lincoln Park Zoo, free to enter and perfect for toddlers to see animals and play in the children's area.
CURRENCY0, 3 hours

12:30 PM

Lunch at R.J. Grunts

Head to R.J. Grunts for lunch, where you can find an all-you-can-eat salad bar and kid-friendly meals.
CURRENCY45, 1 hour

1:30 PM

Visit Maggie Daley Park

Spend the afternoon at Maggie Daley Park where toddlers can enjoy the playground, climbing walls, and a mini-golf course.
CURRENCY0, 2.5 hours

4:00 PM

Treats from Jeni's Splendid Ice Creams

Grab delicious ice cream from Jeni's Splendid Ice Creams, a perfect treat to cool down after a fun day.
CURRENCY20, 30 minutes

5:00 PM

Dinner at The Hamburger Mary’s

Have a lively dining experience at Hamburger Mary’s, known for its fun atmosphere and great burgers for the whole family.
CURRENCY70, 1.5 hours
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Day 4: Fun Day

Chicago, IL on March 8, 2025

8:00 AM

Breakfast at Brunch

Fuel up with brunch at Brunch, which serves delicious breakfast burritos and pancakes that toddlers will love.
CURRENCY50, 1 hour

9:30 AM

Visit the Chicago Children's Museum

Let the kids explore the interactive exhibits at the Chicago Children’s Museum, geared towards young learners.
CURRENCY50, 2 hours

11:30 AM

Lunch at Navy Pier Food Court

Grab a diverse selection of kid-friendly meals at Navy Pier Food Court while enjoying views of Lake Michigan.
CURRENCY60, 1 hour

1:00 PM

Ride the Centennial Wheel

Take a ride on the Centennial Wheel for a fun view of the city, perfect for families and toddlers.
CURRENCY20, 1 hour

2:00 PM

Play at the Navy Pier Park

Let your toddlers enjoy the water play area and carousel at Navy Pier's park, full of engaging activities.
CURRENCY0, 2 hours

4:30 PM

Dinner at Luminarias Restaurant

After a full day of fun, dine at Luminarias for an upscale twist on family dining with stunning lake views.
CURRENCY80, 1.5 hours
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Day 5: Return Day

Chicago, IL to Madison, WI on March 9, 2025

8:00 AM

Breakfast at The Sweet Maple Café

Start your final day with breakfast at The Sweet Maple Café, where families enjoy made-to-order pancakes and fresh juices.
CURRENCY50, 1 hour

9:00 AM

Visit the Chicago Botanic Garden

Before heading back to Madison, take a serene morning stroll through the Chicago Botanic Garden, which is toddler-friendly.
CURRENCY0, 1.5 hours

10:30 AM

Depart for Madison

Start your drive back home after a memorable trip filled with adventure and family bonding.
CURRENCY0, 2 hours
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