Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version
Viewed by 60 travelers

7-Day City Experiences Itinerary: Chicago, Wisconsin, Saint Louis

Friday, September 8: Arrival in Chicago

Welcome to the Windy City! Start your day with a visit to Millennium Park, where you can marvel at the iconic Cloud Gate sculpture, also known as "The Bean." In the afternoon, explore the Art Institute of Chicago, home to a vast collection of artworks spanning different eras and cultures. In the evening, head to Navy Pier for breathtaking views of Lake Michigan and enjoy the lively atmosphere with various entertainment options.

  • Millennium Park: Free, 2-3 hours
  • Art Institute of Chicago: $25 admission, 3-4 hours
  • Navy Pier: Free admission, time spent varies
Saturday, September 9: Chicago Exploration

Embark on an architectural adventure with a Chicago River Architecture Cruise in the morning, where you can admire the city's stunning skyline and learn about its rich architectural history. In the afternoon, visit the Field Museum to delve into natural history and explore fascinating exhibits. Wrap up the day by indulging in Chicago's famous deep-dish pizza at one of the city's renowned pizzerias.

  • Chicago River Architecture Cruise: $40-55, 1.5-2 hours
  • Field Museum: $26 admission, 2-3 hours
  • Deep-dish pizza dinner: $20-30 per person, time spent varies
Sunday, September 10: Wisconsin Adventure

Take a scenic drive to Milwaukee, Wisconsin, in the morning. Begin by exploring the Milwaukee Art Museum, known for its impressive collection and iconic Quadracci Pavilion. In the afternoon, visit the Harley-Davidson Museum to delve into the history of this legendary motorcycle brand. Enjoy the evening by strolling along the Riverwalk and indulging in local cuisine at one of the city's breweries or restaurants.

  • Milwaukee Art Museum: $19 admission, 2-3 hours
  • Harley-Davidson Museum: $10-20 admission, 2-3 hours
  • Exploring Riverwalk and dining: Cost varies, time spent varies
Monday, September 11: Exploring Chicago's Neighborhoods

Dedicate the day to exploring Chicago's vibrant neighborhoods. Start in Lincoln Park, where you can visit the Lincoln Park Zoo and stroll through the picturesque Lincoln Park itself. In the afternoon, head to Wicker Park for unique boutiques, trendy cafes, and street art. Finish the day by experiencing the lively atmosphere of Chicago's Chinatown and enjoying delicious Asian cuisine.

  • Lincoln Park Zoo: Free admission, 2-3 hours
  • Exploring Wicker Park: Cost varies, time spent varies
  • Chinatown: Cost varies, time spent varies
Tuesday, September 12: Journey to Saint Louis

Travel to Saint Louis, Missouri, in the morning. Start by exploring the iconic Gateway Arch, where you can take a tram ride to the top for panoramic views of the city and the Mississippi River. In the afternoon, visit the City Museum, a unique attraction featuring a mix of architectural elements and interactive exhibits. End the day with a visit to the Soulard neighborhood and enjoy its vibrant nightlife.

  • Gateway Arch: $13-16 admission, 2-3 hours
  • City Museum: $15-18 admission, 3-4 hours
  • Exploring Soulard: Cost varies, time spent varies
Wednesday, September 13: Saint Louis Highlights

Explore Forest Park, a sprawling urban park featuring attractions such as the Saint Louis Art Museum, Saint Louis Zoo, and the Missouri History Museum. Spend the afternoon at the Botanical Gardens, immersing yourself in nature's beauty. In the evening, head to The Hill neighborhood to savor delicious Italian cuisine.

  • Forest Park: Free, time spent varies
  • Missouri Botanical Garden: $12 admission, 2-3 hours
  • Exploring The Hill: Cost varies, time spent varies
Thursday, September 14: Farewell to the Midwest

Wrap up your trip with a visit to the City Museum in the morning, where you can explore more of its fascinating exhibits. In the afternoon, take a leisurely stroll along the Delmar Loop, filled with shops, galleries, and restaurants. Bid farewell to the Midwest with a dinner at one of Saint Louis' renowned barbecue spots.

  • City Museum: $15-18 admission, 2-3 hours
  • Delmar Loop: Cost varies, time spent varies
  • Saint Louis barbecue dinner: $15-30 per person, time spent varies

Hidden Gems and Local Favorites

While exploring Chicago, be sure to visit the Garfield Park Conservatory, a stunning indoor botanical garden that offers a serene escape from the bustling city. In Wisconsin, consider a detour to Door County, known for its charming small towns, picturesque landscapes, and delicious cherry pie. Lastly, in Saint Louis, don't miss the opportunity to explore The Loop, a vibrant neighborhood filled with eclectic shops, live music venues, and delicious global cuisine.

For hotel and flight prices, you can check here.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version