14-Day Family-Friendly Road Trip Itinerary from Naperville to Chicago

Day 1: Explore Naperville

Naperville, Illinois

8:00AM

Breakfast at Egg Harbor Cafe

Start your day with a hearty breakfast featuring their signature stuffed French toast and fresh-squeezed juices.
Head to Egg Harbor Cafe located in downtown Naperville.
USD20, 1 hour

9:30AM

Visit the Naperville Riverwalk

Stroll along the beautiful Riverwalk that offers picturesque views, fountains, and historical landmarks.
Walk from the cafe to the Riverwalk; it's a short 5-minute walk.
Free, 2 hours

12:00PM

Lunch at Lou Malnati's Pizzeria

Savor the iconic Chicago-style deep-dish pizza with family at this local favorite.
Drive to Lou Malnati's; it's a quick 5-minute drive.
USD50, 1.5 hours

2:00PM

Visit Naper Settlement

Step back in time at this living history museum featuring historic buildings and engaging exhibits.
It's a 10-minute drive from the pizza place.
USD40 for the family, 2 hours

4:30PM

Play at Centennial Beach

Cool off at this unique beach experience with swimming and sandy lounging.
Just a 5-minute drive from Naper Settlement.
USD30, 2 hours

7:00PM

Dinner at The 5th Avenue

Enjoy a family-friendly dining experience with burgers and pasta in a casual setting.
10 minutes drive from Centennial Beach.
USD70, 1.5 hours
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Day 2: Day Trip to Aurora

Aurora, Illinois

8:30AM

Breakfast at the Blackberry Market

Fuel up with locally sourced breakfast favorites such as omelets and gourmet waffles.
Drive 30 minutes to Aurora.
USD40, 1 hour

10:00AM

Visit the SciTech Hands On Museum

Engage with fun science exhibits that are perfect for families and kids of all ages.
A quick 10-minute drive from the cafe.
USD40 for the family, 2 hours

12:30PM

Lunch at Portillo's

Experience classic Chicago fast food – try the Italian beef sandwiches!
Drive 10 minutes to Portillo’s.
USD50, 1 hour

2:00PM

Explore the Phillips Park Zoo

Visit this small, family-friendly zoo featuring various animal exhibits and lovely park grounds.
Just a 15-minute drive from Portillo's.
Free, 2 hours

4:30PM

Relax at the park

Take a scenic walk or let the kids play at Phillips Park.
Walk around the zoo area.
Free, 1.5 hours

6:00PM

Dinner at The Fox Valley Spot

Enjoy a casual dinner in a family-friendly atmosphere with delicious American comfort food.
Drive 10 minutes from Phillips Park.
USD60, 1.5 hours
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Day 3: Shopping and Dining in Oak Brook

Oak Brook, Illinois

8:00AM

Breakfast at The Original Pancake House

Enjoy a delightful breakfast with their renowned pancakes and crepes.
Drive 30 minutes to Oak Brook.
USD40, 1 hour

9:30AM

Shop at Oakbrook Center

Explore this luxury shopping center with a variety of shops and outdoor spaces.
On foot in Oak Brook Center.
Free to explore, 3 hours

12:30PM

Lunch at Maggiano's

Indulge in family-style Italian dining with savory pastas and desserts.
Walk through the shopping center to Maggiano's.
USD70, 1.5 hours

2:00PM

Visit the Brookfield Zoo

Head over to the nearby zoo for a fun day with wildlife, attractions and interactive exhibits.
Drive 15 minutes from Maggiano's.
USD80 for the family, 3 hours

5:30PM

Enjoy the outdoor exhibit

Take some time at the zoo’s outdoor exhibits before heading to dinner.
Walk to the outdoor displays.
Free, 1 hour

6:30PM

Dinner at Birrieria Zaragoza

Classic Mexican cuisine, perfect for a casual family meal with flavorful dishes.
Drive 15 minutes from Brookfield Zoo.
USD50, 1.5 hours
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Day 4: Cultural Stops in Elmhurst

Elmhurst, Illinois

8:00AM

Breakfast at Egg Harbor Cafe

Return to Egg Harbor Cafe for a delicious family breakfast before hitting the road.
Drive 20 minutes to Elmhurst.
USD40, 1 hour

9:30AM

Visit Elmhurst Art Museum

Enjoy contemporary art exhibits and family-friendly activities at the local art museum.
Just a short drive of 5 minutes.
USD40 for the family, 1.5 hours

11:00AM

Explore Elmhurst History Museum

Learn about local history through interactive exhibits and informative displays.
A short walk from the art museum.
USD30 for the family, 1.5 hours

12:30PM

Lunch at L. Woods Tap and Pine Lodge

Savor flavorful comfort food, particularly their BBQ dishes and burgers.
Drive 10 minutes to lunch.
USD60, 1.5 hours

2:00PM

Visit Wilder Park

Enjoy the beautiful gardens and playgrounds with the kids after lunch.
Drive 5 minutes to Wilder Park.
Free, 2 hours

4:30PM

Walk the Elmhurst City Centre

Explore the local shops and possibly grab a coffee treat for the afternoon.
10 minutes drive from Wilder Park.
Free to explore, 1.5 hours

6:00PM

Dinner at Francesca's Bellezza

Dine at this cozy Italian spot featuring delicious entrees and desserts.
10 minutes drive to Francesca's.
USD70, 1.5 hours
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Day 5: City Adventure in Chicago

Chicago, Illinois

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Dive into a unique brunch from their expansive pancake menu – a perfect start for a busy day.
Drive 30 minutes to Chicago.
USD50, 1 hour

9:30AM

Visit the Field Museum

Explore numerous engaging exhibits, including Sue, the T-Rex, which are sure to fascinate the kids.
Drive about 15 minutes to the museum.
USD80 for the family, 3 hours

12:30PM

Lunch at Lou Malnati's (nearby)

Relish a delicious deep-dish pizza again at this famous establishment.
Short drive from the Field Museum.
USD50, 1.5 hours

2:00PM

Explore Shedd Aquarium

Enjoy a variety of aquatic exhibits that are perfect for families to explore together.
A quick 10-minute walk from lunch.
USD80 for the family, 2.5 hours

4:30PM

Relax at Millennium Park

Take a leisurely stroll through the iconic park and feel free to snap family photos at Cloud Gate.
A short drive or walk to the park.
Free, 1 hour

6:00PM

Dinner at Giordano's

Enjoy another take on deep-dish pizza or Italian classics at this beloved Chicago pizzeria.
Drive about 10 minutes from Millennium Park.
USD50, 1.5 hours
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Day 6: Nature and Fun in Skokie

Skokie, Illinois

8:00AM

Breakfast at Corner Bakery Cafe

Start your day with a quick bite of fresh baked goods and breakfast sandwiches.
Drive 30 minutes to Skokie.
USD30, 1 hour

9:30AM

Visit Skokie Northshore Sculpture Park

Explore the beautiful sculptures in the park while taking a leisurely walk with your family.
Just a quick drive 5 minutes away.
Free, 1.5 hours

11:00AM

Discover the Skokie Heritage Museum

Learn about the historic significance of the village and its cultural heritage.
Drive 10 minutes to the museum.
USD20 for the family, 1 hour

12:30PM

Lunch at The Bagelers

Enjoy a delightful lunch featuring delicious bagels and creative sandwiches.
5 minutes drive from the museum.
USD40, 1 hour

2:00PM

Visit Skokie Park District Attractions

Spend time at the park district with activities like a splash pad or playgrounds.
Only a few minutes drive to parks.
Free, 2 hours

4:30PM

Take a Family Bike Ride

Rent bikes and pedal through trails, enjoying the greenery and activity.
Bike rentals available at nearby parks.
USD40 for rentals, 2 hours

6:30PM

Dinner at Lou Malnati’s

End the day with one more round of Chicago-style deep-dish pizza.
Definitely the favorite from yesterday's explorations.
USD50, 1.5 hours
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Day 7: College Town Charm in Evanston

Evanston, Illinois

8:00AM

Breakfast at The Stained Glass

Enjoy a cozy breakfast featuring artisanal coffee and house-made pastries.
Drive 20 minutes to Evanston.
USD30, 1 hour

9:30AM

Visit the Block Museum of Art

Enjoy contemporary art experiences that often have family-friendly options.
Just a short drive of 5 minutes.
Free, 1.5 hours

11:00AM

Explore Northwestern University's Campus

Take a leisurely walk through one of the most beautiful campuses in the country.
Walking distance from the museum.
Free, 1 hour

12:30PM

Lunch at The Collar Room

A casual spot known for its sandwiches and laid-back vibe, perfect for families.
A 10-minute walk from campus.
USD50, 1.5 hours

2:00PM

Stroll along the Evanston Lakefront

Enjoy scenic views by Lake Michigan, allowing time for kids to explore and play.
A quick drive or a long walk to the lakefront.
Free, 1.5 hours

4:00PM

Visit the Noyes Cultural Arts Center

Check out art galleries and workshops suitable for kids and families.
A short drive from the lakefront.
Free, 1 hour

5:30PM

Dinner at Dixie Kitchen & Bait Shop

Enjoy Southern comfort food, including gumbo and fried chicken in a relaxed atmosphere.
Drive 10 minutes from the cultural center.
USD60, 1.5 hours
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Day 8: Adventure in Lincoln Park

Lincoln Park, Illinois

8:00AM

Breakfast at Toast

Dig into healthy breakfast options with unique twists on classic dishes.
Drive 30 minutes to Lincoln Park.
USD40, 1 hour

9:30AM

Visit Lincoln Park Zoo

Free of charge, this charming city zoo offers interactions with animals and great exhibits.
Just a short walk from Toast.
Free, 2 hours

11:30AM

Relax at Lincoln Park Conservatory

Experience beautiful gardens and unique plant species in this serene conservatory.
Walking distance from the zoo.
Free, 1.5 hours

1:00PM

Lunch at Café Ba-Ba-Reeba!

Enjoy a family-style meal with tapas, paellas, and other delicious offerings.
A quick drive from the conservatory.
USD70, 1.5 hours

2:30PM

Explore the Peggy Notebaert Nature Museum

Engage in family-friendly exhibits about the local ecosystem and wildlife.
A short drive from the restaurant.
USD50 for the family, 2 hours

5:00PM

Walk along Lakefront Trail

Take a scenic stroll or bike ride along the lakefront while enjoying the beautiful views.
Head to the nearby waterfront.
Free, 1.5 hours

6:30PM

Dinner at Gino's East

Savor the world-famous Chicago-style deep-dish pizza in a vibrant setting.
A short drive to Gino's.
USD50, 1.5 hours
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Day 9: Discover Hyde Park

Chicago, Illinois

8:00AM

Breakfast at Medici on 57th

Enjoy a comforting breakfast in an artistic atmosphere with plenty of options for everyone.
Drive about 30 minutes to Hyde Park.
USD40, 1 hour

9:30AM

Visit the Museum of Science and Industry

Delve into fun and interactive science exhibits appropriate for all ages.
Just a quick drive from breakfast.
USD80 for the family, 3 hours

12:30PM

Lunch at The Promontory

Savor a blend of American dishes while enjoying great views of Hyde Park.
Drive just 5 minutes away.
USD70, 1.5 hours

2:00PM

Explore the University of Chicago

Take a leisurely walk through campus and enjoy the remarkable architecture and gardens.
Walking distance from lunch.
Free, 1 hour

3:30PM

Visit the Robie House

Discover the architectural masterpiece designed by Frank Lloyd Wright.
Drive 10 minutes from the university.
USD40 for the family, 1.5 hours

5:00PM

Relax at Jackson Park

Let the kids play while you enjoy the gardens and a lovely park atmosphere.
A short drive from Robie House.
Free, 1.5 hours

6:30PM

Dinner at Regia

Enjoy Brazilian cuisine and shareable dishes in a friendly setting.
Drive 10 minutes for dinner.
USD60, 1.5 hours
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Day 10: Relax in Glenview

Glenview, Illinois

8:00AM

Breakfast at Walker Brothers

Savor heavenly pancakes and eggs benedict to kickstart an exciting day!
Drive 30 minutes to Glenview.
USD40, 1 hour

9:30AM

Explore the Glenview Park District

Enjoy various activities and playgrounds designed for family fun.
Just 5 minutes to the park district.
Free, 2 hours

12:00PM

Lunch at The Cheesecake Factory

Treat yourself to a wide array of dishes and, of course, their famous cheesecakes.
Drive 10 minutes to The Cheesecake Factory.
USD70, 1.5 hours

1:30PM

Visit the Kohl Children's Museum

Engage the little ones in creative play and interactive exhibits tailored to kids.
A short drive of 5 minutes.
USD60 for the family, 2 hours

3:30PM

Enjoy the Glenview Farmers Market

Explore fresh produce and local goods while soaking in the community atmosphere.
Drive about 10 minutes to the market.
Free, 1 hour

5:00PM

Dinner at CPK (California Pizza Kitchen)

End the day with pizzas and comfort food in a casual family environment.
Drive a quick 10 minutes for dinner.
USD50, 1.5 hours
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Day 11: Family Fun in Northbrook

Northbrook, Illinois

8:00AM

Breakfast at Egg Harbor Cafe

Enjoy fresh breakfast selections made from local ingredients to start your day right.
Drive 15 minutes to Northbrook.
USD40, 1 hour

9:30AM

Visit Northbrook Court

Shop and explore this family-friendly mall with both shops and restaurants.
Walk around the mall.
Free to explore, 2 hours

12:00PM

Lunch at Maggiano's Little Italy

Indulge in family-style dining with generous portions of Italian favorites.
Take a short walk to Maggiano's.
USD70, 1.5 hours

1:30PM

Spend time at the Northbrook Park District

Let kids run around at outdoor parks and playgrounds to burn off some energy.
A quick drive to a park.
Free, 2 hours

4:00PM

Visit the Northbrook Library

Take a moment to relax and read or engage in library activities designed for children.
Short drive from the park.
Free, 1.5 hours

5:30PM

Dinner at The Capital Grille

Enjoy a more upscale dining experience while still being family-friendly in ambiance.
Drive 10 minutes for dinner.
USD100, 2 hours
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Day 12: History and Culture in Wheaton

Wheaton, Illinois

8:00AM

Breakfast at Egg Harbor Cafe

Revisit the favorite breakfast spot before heading out to Wheaton.
Drive 30 minutes to Wheaton.
USD40, 1 hour

9:30AM

Visit the DuPage County Historical Museum

Discover the local history through diverse exhibits in this engaging museum.
Drive 10 minutes to the museum.
USD30 for the family, 1.5 hours

11:00AM

Explore Cantigny Park

Beautiful gardens and a mini-museum await you at this lovely park great for family pics.
Drive 15 minutes to Cantigny.
Free, but some attractions may have a fee., 2 hours

1:00PM

Lunch at Aurelio's Pizza

Delight in scrumptious thin-crust pizza, perfect for sharing with the family.
Short drive from Cantigny.
USD50, 1.5 hours

2:30PM

Visit the Wheaton Park District

Experience local attractions and take part in programs fun for families.
A quick drive to the park.
Free, 1.5 hours

4:00PM

Enjoy the Wheaton Sports Center

Engage in sports activities or just relax at the center designed for family fun.
Short drive to the center.
Free, some activities might have a fee., 1.5 hours

5:30PM

Dinner at Culver's

Savor delicious butter burgers and custard while enjoying a casual family dining experience.
Drive 10 minutes from the sports center.
USD40, 1.5 hours
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Day 13: Final Day in Lombard

Lombard, Illinois

8:00AM

Breakfast at The Original Pancake House

Enjoy the best pancakes in Lombard to kickstart your day.
Drive 30 minutes to Lombard.
USD40, 1 hour

9:30AM

Visit the Lilacia Park

Explore the beautiful gardens and trails, they're wiggle-perfect for kids to roam and explore.
Drive 10 minutes around Lombard.
Free, 2 hours

11:30AM

Explore the Lombard Historical Society Museum

Learn about local history and enjoy the small exhibits designed for families.
A quick drive to the museum.
USD20 for the family, 1 hour

1:00PM

Lunch at Portillo’s

Gather for lunch back at Portillo’s to indulge in delicious sandwiches and treats.
Drive about 10 minutes to reach Portillo's.
USD50, 1.5 hours

2:30PM

Visit Yorktown Center

Last-minute shopping and family fun at this shopping center for souvenirs.
A quick drive from Portillo's.
Free to explore, 1.5 hours

4:00PM

Relax at a Local Park

Wind down in the outdoors at a nearby park, letting the kids play one last time.
Drive around to find a nearby park.
Free, 1 hour

5:30PM

Dinner at Dutch Brothers Coffee

Gather for a cozy dinner enjoying light bites with fantastic coffee options.
Drive 10 minutes to reach the coffee shop.
USD30, 1.5 hours
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Day 14: Homeward Bound to Naperville

Naperville, Illinois

8:00AM

Grab Quick Breakfast at Starbucks

Have a fast-paced breakfast and coffee for the road before heading home.
Drive 20 minutes to Starbucks.
USD20, 30 minutes

8:30AM

Head to Naperville

Take the scenic route back home, reflecting on your wonderful adventure.
Drive 30 minutes back to Naperville.
Free, 30 minutes
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