Chicago 6 Day Itinerary

6-Day Chicago Itinerary: A Deep Dive into the Windy City

This itinerary offers a balanced mix of iconic landmarks, hidden gems, diverse experiences, and delicious food, perfect for a first-time visitor.

Things to Know:

  • Weather: Chicago’s weather is notoriously unpredictable. Be prepared for anything with layers, as temperatures can fluctuate dramatically throughout the day.
  • Neighborhoods: This itinerary focuses on downtown attractions, but don’t hesitate to venture into different neighborhoods for a more authentic experience (e.g., Wicker Park for trendy restaurants and shops, Lincoln Park for its zoo and parks).
  • Transportation: Chicago has an excellent public transportation system. You can easily get around using the “L” train (CTA), buses, or taxis. Consider purchasing a Ventra card for easy travel on the CTA.

Day 1: Magnificent Mile & Deep Dish Pizza

  • Morning: Explore the iconic Magnificent Mile, starting with a walk along Michigan Avenue, window shopping at luxury stores like Tiffany & Co. and Neiman Marcus, and admiring the architecture.

  • Afternoon: Indulge in a classic Chicago experience by enjoying a delicious deep dish pizza lunch. Some popular spots for deep dish include:

    • Lou Malnati’s Pizzeria: Enjoy a legendary deep dish experience at one of Chicago’s most beloved pizzerias. (Try the “The Malnati” or “Chicago Classic” for an authentic taste)
    • Pequod’s Pizza: For a crispy, caramelized crust and a unique “pan pizza” style.

  • Evening: Head to Pizzeria Uno (the original deep dish spot!) or Giordano’s for a taste of the famous Chicago-style deep dish.

Day 2: Art & Architecture

  • Morning: Visit the Art Institute of Chicago, home to masterpieces by renowned artists like Grant Wood, Monet, and Picasso.
  • Afternoon: Take an architectural boat tour along the Chicago River to marvel at the city’s iconic skyline and learn about its history from a unique perspective.
  • Evening: Enjoy a fine dining experience with breathtaking views at Signature Room at the 95th.

Day 3: Millennium Park & Navy Pier

  • Morning: Explore the Cloud Gate sculpture (aka “The Bean”) and Crown Fountain, enjoying the reflections and interactive art.
  • Afternoon: Wander through Millennium Park, taking in the Crown Fountain, Buckingham Fountain, and the stunning architecture of Millennium Park.
  • Evening: Indulge in Chicago’s vibrant nightlife by visiting a rooftop bar like Cindy’s Rooftop or The Roof at Park Hyatt Chicago.

Day 4: Museums & History

  • Morning: Immerse yourself in history at the Field Museum, exploring dinosaur fossils, ancient artifacts, and cultural exhibits.
  • Afternoon: Wander through the Museum of Science and Industry for a fascinating journey into science and technology.
  • Evening: Enjoy the lively atmosphere and stunning views of Lake Michigan from the Skydeck Chicago.

Day 5: Architecture & Food

  • Morning: Explore the city’s architectural gems with a visit to the Chicago Architecture Center, where you can learn about the history and design of skyscrapers.

  • Afternoon: Climb the stairs to the top of the John Hancock Center, enjoying the panoramic views of the city and its famous architecture.

  • Evening: For a unique dining experience, try Pizzeria Due, the second location of Chicago’s first deep dish pizza restaurant.

Day 6: Parks & Architecture

  • Morning: Enjoy a picnic and a leisurely stroll through the beautiful Millennium Park, taking in the architecture of the city around you.
  • Afternoon: Explore the iconic Willis Tower (formerly Sears Tower), enjoy the view from the top.

Evening: For a final farewell to Chicago’s architecture, try The Signature Lounge, located on the 96th floor of the Hancock building, for a drink and breathtaking views.

Other things to consider:

  • Ventra Card: A must-have for navigating the public transportation system in Chicago.
  • Deep Dish Pizza Options: This itinerary features two popular deep dish pizza spots, but there are many others! Explore options like Lou Malnati’s Pizzeria (multiple locations), Giordano’s (also multiple locations), Pequod’s Pizza (for a deep dish experience with a thin, crispy crust) and Garrett Popcorn Shops (known for their “Garrett Mix” of caramel and cheese popcorn).
  • Deep Dish Pizza Experiences: Consider the variety of deep dish pizza experiences Chicago offers.

Enjoy other attractions:

  • Navy Pier: While you’re there, take a ride on the Centennial Wheel, visit the Chicago Children’s Museum or the Chicago Shakespeare Theater, or enjoy free concerts and events.

Things to do in Chicago:

  • Explore other neighborhoods:

    • Lincoln Park Zoo: This free zoo is a great place to spend an afternoon with the family. You can see lions, tigers, penguins, and more!

  • Museum of Science and Industry: A fantastic choice for both adults and kids, this museum offers interactive exhibits and hands-on experiences.

  • Chicago Riverwalk: A scenic pathway along the Chicago River, perfect for a leisurely walk with stunning views of the city’s skyline.

  • Deep Dish Pizza Tour: For a truly immersive experience, consider trying different deep dish pizzerias for a taste comparison.

Enjoy the “cityscape” experience:

  • Architecture & Boat Tours: These are fantastic ways to see the city from a unique perspective and learn about its architectural history.
  • Navy Pier Ferris Wheel: A Chicago icon with breathtaking views of the lake and cityscape.

Things to do for a “Taste of Chicago”:

  • Centennial Wheel: Enjoy a ride on this iconic Ferris wheel, which is located on the Navy Pier and offers stunning views of the city.
  • Skydeck Chicago: Indulge in a deep dish pizza experience with a breathtaking view of the city from the 103rd floor.

Enjoy other “Chicago” experiences:

  • Magnificent Mile Shopping: Experience the vibrant shopping scene on Michigan Avenue, known for its upscale boutiques and department stores.

  • Navy Pier Fireworks: Enjoy the spectacular fireworks display over Lake Michigan (check schedule for availability).

  • Architecture Walking Tour: Explore Chicago’s architectural wonders up close by walking the Magnificent Mile or visiting other historical landmarks in the city.

  • Chicago Riverwalk Boat Tours: Learn about the city’s history and architecture through a guided boat tour on the river, enjoying the unique perspective of the architecture from the water.

Food Recommendations:

  • Deep Dish Pizza: A classic Chicago dish with a deep, buttery crust and generous toppings. Try Pizzeria Uno, Lou Malnati’s, Pequod’s Pizza for a traditional experience, or Giordano’s (for a truly unique experience) for a deep dish pizza.

  • Chicago Hot Dogs: Enjoy a Chicago-style hot dog with all the classic toppings: mustard, relish, onions, pickles, tomatoes, and sport peppers.

  • Chicago Italian Beef: A delicious local sandwich that’s perfect for a taste of “Chicago” food.

  • Garrett Popcorn Shops: Indulge in a bag of their famous Chicago-style popcorn.

Tips:

  • Buy a Ventra card: This makes using public transportation much easier and cheaper.

  • Get tickets online: Many attractions offer discounted tickets if you buy them in advance, so it’s worth checking the websites for the “Chicago” experiences.

  • Bring comfortable shoes: You’ll be doing a lot of walking!

  • Dress in layers: The weather in Chicago can change quickly.

  • Consider the time of year: Chicago is known for its extreme weather, so summer is ideal for enjoying the city’s outdoor attractions.

Chicago-Style Pizza Options:

  • Deep Dish Pizza: This is a must-try for any visitor to Chicago.
  • Pizzeria Uno: For a classic deep dish experience, try the “Deep Dish” pizza at Pizzeria