5 Day Naperville Adventure: History, Food, and Fun

Explore the charm of Naperville - a perfect blend of small-town feel and modern amenities.

22 April 2023

Naperville, a suburb of Chicago, offers a picturesque downtown with a mix of historic architecture and modern amenities. Visitors can stroll along the Riverwalk, a scenic path dotted with fountains and artwork, or explore the eclectic shops and restaurants that line the streets. Sports fans won't want to miss a visit to North Central College's Benedetti-Wehrli Stadium, a state-of-the-art facility that has hosted a variety of athletic events.

Travel plan

Getting latest place information
Day 1

Arriving in Naperville

  • Check into the Hotel Indigo Naperville Riverwalk for a stylish and comfortable stay.
  • Walk along the beautiful Riverwalk to get a feel for the town's charm and character.
  • Stop by Anderson's Bookshop, a Naperville institution where you can find both bestsellers and local gems.
  • Grab lunch at Quigley's Irish Pub, a cozy spot with delicious Irish classics and live music on weekends.
  • Spend an afternoon admiring art at the Naperville Art League Gallery or exploring the unique exhibits at the DuPage Children's Museum.
Day 2

Discovering History and Culture

  • Start with breakfast at The Lucky Penny Diner and Cafe, a retro-themed eatery with classic American dishes.
  • Visit the Naper Settlement, a living history museum that showcases how Naperville evolved over the centuries.
  • Take a tour of the Century Memorial Chapel, an iconic venue perfect for weddings and events.
  • Enjoy lunch at Meson Sabika, a Spanish-inspired restaurant with gorgeous patio views and tapas-style dishes.
  • Head to North Central College's Fine Arts Center to catch a show, film screening or concert.
Day 3

Nature and Recreation

  • Begin with a hearty breakfast at Egg Harbor Cafe, known for their fresh and wholesome dishes.
  • Drive to Hidden Lake Forest Preserve to hike or bike through 1,200 acres of woodlands, prairies and lakes.
  • Rent a kayak or paddleboat to explore the waters of Centennial Beach, a historic site turned aquatic center.
  • Have lunch al fresco on the patio of Hugo's Frog Bar & Fish House, a seafood institution with live jazz music.
  • Go shopping at the Naperville Farmers Market, where you can find organic produce, artisanal goods and more.
Day 4

Foodie Tour

  • Try the decadent crepes and waffles at La Sorella di Francesca for breakfast.
  • Go on a food tour with Naperville Bites and Sights to sample the town's best treats and learn about its history.
  • Satisfy your sweet tooth at DeEtta's Bakery, a beloved spot with cookies, cupcakes and custom cakes.
  • Get a taste of Italy at Lou Malnati's Pizzeria, where their deep-dish pizza is a legend in Naperville and beyond.
  • Have dinner at Catch 35 Naperville, a stylish seafood restaurant with fresh catches and live music.
Day 5

Farewell, Naperville

  • Get a caffeine boost at Sparrow Coffee, which offers artisanal coffee and precision brewing techniques.
  • Browse the upscale shops and boutiques in Downtown Naperville, from fashion to homeware to gadgets.
  • Have a final meal at SixtyFour, a wine bar with elevated food options and more than 64 wines by the glass.
  • Say goodbye to Naperville with a walk around the town center and a ride on the whimsical Naperville Trolley.
  • Depart from the Hotel Indigo Naperville Riverwalk with fond memories and a newfound appreciation for this charming town.

How to get there

Plane

The best way to reach Naperville, United States by plane is to fly to Chicago O'Hare International Airport and then take a taxi, bus, or train to Naperville.

Car

The best way to reach Naperville, United States by car is to drive on I-88 W from Chicago. The trip takes around 45 minutes depending on traffic.

Train

There is a Metra train that runs from Chicago Union Station to Naperville Station, making it the best way to reach Naperville by train.

Boat

There is no direct boat transportation to Naperville, United States. However, you can take a boat tour from Chicago to Naperville on the Chicago River.

Bus

Taking a bus from Chicago to Naperville is the best way to reach the city by bus. Greyhound offers regular bus service from Chicago to Naperville.

More travel plans

Weekend Wanderlust: Exploring Naperville in 2 Days

Naperville is a charming city located in the state of Illinois, known for its beautiful parks and historic buildings. As a tourist, you can explore the Naper Settlement Museum, which showcases the city's history, or visit the DuPage Children's Museum for a fun and educational experience. Additionally, you can unwind at the Naperville Riverwalk, a picturesque pathway along the DuPage River.

Naperville: A 4-Day Family Adventure on a Budget

Naperville, United States is the perfect destination for a family-friendly trip, offering a mixture of outdoor adventures and educational experiences. Explore the scenic Riverwalk, an expansive pathway lined with parks and sculptures, where kids can enjoy paddle boating or picnicking by the river. Visit the DuPage Children's Museum, filled with interactive exhibits that engage children of all ages, providing an entertaining and educational day for the whole family.

Long weekend romance in charming Naperville

Naperville, located just a short drive from the bustling city of Chicago, is the perfect spot for a romantic getaway. With a charming downtown area featuring boutique shops and a wide variety of dining options, couples can enjoy a leisurely stroll before settling down for a candlelit dinner. The town's idyllic riverwalk, complete with picturesque bridges and fountains, provides the perfect backdrop for a romantic stroll.

Nifty Naperville: A Thrilling 2-Day Family Adventure

Naperville, located in the United States, is a perfect destination for a family-friendly trip. This vibrant city offers something for everyone, from beautiful parks and recreational activities to interactive museums and lively festivals. Explore the Naperville Riverwalk, visit the Naper Settlement to experience history firsthand, and enjoy thrilling water rides at the Centennial Beach for an unforgettable family vacation.