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7-Day Itinerary Traveling to Naperville

Friday, October 6, 2023: Arrival and Local Exploration

Start your trip by arriving in Naperville and checking into your hotel. Take some time to explore the downtown area, known for its charming shops, restaurants, and the historic Riverwalk. In the morning, enjoy a leisurely stroll along the scenic Riverwalk and admire the beautiful fall foliage. For lunch, try a local favorite, Egg Harbor Cafe, known for its delicious breakfast and brunch options. Spend the afternoon visiting the Naper Settlement, an outdoor history museum where you can learn about the city's past. In the evening, head to Two Brothers Barrel House for dinner and enjoy their unique craft beers and tasty food.

  • Check hotel and flight prices on Kayak.
  • Riverwalk: Free, 1-2 hours
  • Egg Harbor Cafe: $10-$15 per person, 1 hour
  • Naper Settlement: $10 per person, 2-3 hours
  • Two Brothers Barrel House: $15-$30 per person, 2 hours
Saturday, October 7, 2023: Museums and Art

Start your day with a visit to the DuPage Children's Museum, a hands-on museum that offers interactive exhibits for children of all ages. Spend the morning exploring the various exhibits and engaging in educational activities. For lunch, try Lou Malnati's Pizzeria, a local favorite known for its deep-dish pizza. In the afternoon, head to the Naperville Art League Gallery, where you can admire the works of local artists. In the evening, catch a show at the bright and modern Pfeiffer Hall, known for its diverse performing arts events.

  • DuPage Children's Museum: $12 per person, 2-3 hours
  • Lou Malnati's Pizzeria: $15-$25 per person, 1 hour
  • Naperville Art League Gallery: Free, 1-2 hours
  • Pfeiffer Hall: Ticket prices vary, 2-3 hours
Sunday, October 8, 2023: Outdoor Recreation

Spend your day surrounded by nature in Naperville's parks. Start your morning with a visit to the Morton Arboretum, a sprawling outdoor museum featuring stunning gardens, walking trails, and an impressive collection of trees. Explore the arboretum and enjoy the beautiful fall colors. Pack a picnic lunch to enjoy in the peaceful surroundings. In the afternoon, head to the Whalon Lake Dog Park, a spacious park where your furry friends can run and play. Take a leisurely walk around the lake or simply relax by the water. As the day comes to an end, catch a scenic sunset at the Naperville Riverwalk Park.

  • Morton Arboretum: $15 per person, 3-4 hours
  • Whalon Lake Dog Park: Free, 2-3 hours
  • Naperville Riverwalk Park: Free, 1-2 hours
Monday, October 9, 2023: Shopping and Dining

Start your day with some retail therapy at the Chicago Premium Outlets, located just a short drive away from Naperville. Explore the wide variety of stores and score some great deals on designer brands. For lunch, head back to Naperville and try Jackson Avenue Pub, a popular local spot known for its delicious burgers and cozy atmosphere. In the afternoon, visit the Naperville Historic District, where you can find a mix of boutique shops, cafés, and art galleries. In the evening, dine at Meson Sabika, a beautiful Spanish tapas restaurant housed in a historic mansion.

  • Chicago Premium Outlets: Free, price varies based on purchases, 4-6 hours
  • Jackson Avenue Pub: $10-$20 per person, 1 hour
  • Naperville Historic District: Free, 2-3 hours
  • Meson Sabika: $30-$50 per person, 2 hours
Tuesday, October 10, 2023: Day Trip to Chicago

Take a day trip to the bustling city of Chicago, located just a short train ride away from Naperville. Start your day by visiting Millennium Park, where you can see the iconic Cloud Gate sculpture, also known as "The Bean," and enjoy the beautiful landscape. Walk along the Magnificent Mile, a stretch of Michigan Avenue known for its luxury shops and vibrant atmosphere. For lunch, try Portillo's, a Chicago classic known for its hot dogs and Italian beef sandwiches. In the afternoon, visit the Art Institute of Chicago, one of the oldest and largest art museums in the country. Explore the museum and admire its vast collection of artworks. In the evening, consider catching a performance at one of Chicago's famous comedy clubs, such as The Second City or Zanies Comedy Club.

  • Train tickets to Chicago: Estimated cost $5-$10 per person one way, 1 hour
  • Millennium Park: Free, 1-2 hours
  • Magnificent Mile: Free, 2-3 hours
  • Portillo's: $10-$15 per person, 1 hour
  • Art Institute of Chicago: $25 per person, 2-3 hours
  • The Second City or Zanies Comedy Club: Ticket prices vary, 2-3 hours
Wednesday, October 11, 2023: History and Culture

Explore the rich history and cultural heritage of Naperville on this day. Start your morning with a visit to the Naperville Heritage Society, which includes the Century Memorial Chapel and a collection of historic buildings. Learn about the city's early settlers and their contributions to the community. For lunch, try Jimmy's Grill, a local favorite known for its comfort food. In the afternoon, visit the Naperbrook Golf Course for a round of golf or enjoy a leisurely walk around the beautiful grounds. In the evening, catch a performance at the Naperville Municipal Band concert, held at the Wentz Concert Hall.

  • Naperville Heritage Society: $10 per person, 2-3 hours
  • Jimmy's Grill: $10-$20 per person, 1 hour
  • Naperbrook Golf Course: Green fees vary, 2-3 hours
  • Naperville Municipal Band concert: Free, 2-3 hours
Thursday, October 12, 2023: Relaxation and Recreation

Take a day to relax and enjoy some recreational activities in Naperville. Start your day by indulging in a spa treatment at Soleil Spa, known for its rejuvenating massages and facials. Afterward, head to Naperville Sportsman's Club for some outdoor activities like shooting and archery. For lunch, try Heaven on Seven, a Cajun restaurant where you can savor delicious Southern cuisine. In the afternoon, rent a kayak or paddleboard at the Naperville Kayak and explore the nearby lakes. As the day winds down, enjoy a relaxing picnic dinner at the Knoch Knolls Park.

  • Soleil Spa: Prices vary based on services, 2-3 hours
  • Naperville Sportsman's Club: Fees vary based on activities, 2-3 hours
  • Heaven on Seven: $15-$30 per person, 1 hour
  • Naperville Kayak: Rental prices vary, 2-3 hours
  • Knoch Knolls Park: Free, 1-2 hours

Hidden Gems and Local Favorites

For those looking to venture off the beaten path, consider visiting the Naper Settlement's Century Memorial Chapel, a beautifully preserved historic chapel that hosts intimate weddings and events. Another hidden gem is the Riverwalk Eatery, a food stand located along the Riverwalk that offers a variety of tasty snacks and refreshments. Locals also love going to Centennial Beach, an old quarry turned swimming and recreation area where you can enjoy the beach, rent paddleboards, or play beach volleyball.

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