Chicago 3 Day Itinerary

3-Day Chicago Itinerary:

This itinerary focuses on hitting the iconic landmarks and experiences of Chicago while highlighting some unique and off-the-beaten-path options.

Day 1: Downtown Delights

  • Morning: Start your day at Millennium Park, home to Cloud Gate (The Bean), Crown Fountain, and the beautiful Lurie Garden. Explore the interactive art installations and marvel at the city skyline reflected in the park’s centerpiece sculptures.

  • Afternoon: Head to the Art Institute of Chicago, one of the world’s leading art museums, and spend time admiring masterpieces like Grant Wood’s “American Gothic” and Edward Hopper’s “Nighthawks.” Afterwards, take a stroll along the Magnificent Mile, indulging in some shopping or window-shopping if that’s your thing.

  • Evening:

    • Activity: Enjoy a delicious dinner and catch a Broadway show at the Chicago Theatre.

    • Things to do:

      • Take a picture with “The Bean” - Cloud Gate
      • Watch the water spout from the Crown Fountain
      • Explore the modern art collection in the Modern Wing of the Art Institute.
      • Enjoy the beautiful views and architecture along the Chicago Riverwalk.

    • Eat: Enjoy dinner at one of the many restaurants lining the Magnificent Mile, known for its diverse culinary scene.

Day 2: Exploring History & Culture

  • Morning: Take a trip back in time with a visit to the Chicago History Museum. Explore exhibits detailing the city’s past from the Great Chicago Fire to present-day events.

  • Afternoon: Immerse yourself in the architectural wonders of Chicago. Consider a Chicago Architecture Foundation River Cruise for a unique perspective on the city’s skyline, or a walking tour through the city’s diverse neighborhoods.

  • Things to know about the museum:

    • Be sure to check their website for current exhibitions and events.
    • Allow at least 2-3 hours to explore the museum and its various collections.

Afternoon: Venture into the vibrant neighborhood of Wicker Park.

**Evening: **Enjoy a deep-dish pizza feast at Lou Malnati’s Pizzeria followed by a live music experience at The Empty Bottle, a legendary Chicago club known for showcasing up-and-coming artists.

Things to know:

  • Chicago History Museum: Located in the heart of downtown.
  • The Empty Bottle: A historic venue with a focus on independent and punk rock.

Day 3: Neighborhood Vibes & Food Fun

  • Morning: Stroll through the vibrant streets of Lincoln Park, visiting the charming shops and cafes along Armitage Avenue or Clark Street.

  • Things to know about the Chicago Riverwalk:

    • Location: Runs along the Chicago River in the downtown area.

  • Things to do:

    • Walk & Food: Explore the diverse culinary scene of the city, from casual eateries to fine-dining restaurants.

  • Afternoon: Enjoy a picnic and explore the beautiful green spaces of Lincoln Park.

Eat: Try a classic Chicago hot dog at Portillo’s - they are known for their delicious food and unique atmosphere.

  • Other options:

    • Take a walking tour focusing on the culinary history of Chicago.

Things to consider:

  • Transportation: The Chicago Riverwalk is easily accessible by public transportation. The CTA (Chicago Transit Authority) has several bus routes and train stations nearby.

  • Things to do:

    • Visit the Art Institute’s website: Check for specific opening hours and ticket information.

    • Explore the city’s museums: Consider visiting other renowned museums in Chicago, such as the Field Museum or the Museum of Science and Industry, to delve into diverse fields like history, natural sciences, and art.

    • Enjoy a meal at a local restaurant: Chicago is known for its culinary diversity, with options ranging from Michelin-starred restaurants to delicious deep dish pizza available across many neighborhoods. Try Pequod’s Pizza in Lincoln Park!

  • Things to know:

    • Deep-dish pizza: A Chicago staple, be sure to try a slice (or two) at a local establishment.
    • Live music: Enjoy the vibrant music scene by grabbing a meal and enjoying some live music.

Tips:

  • Book your tickets in advance: This will help you avoid queues and secure your preferred time slot.

  • Consider visiting during off-peak hours: The Chicago Riverwalk is less crowded early in the morning or late in the evening, allowing for a more relaxed experience.

  • Enjoy the views: The Magnificent Mile offers stunning views of Lake Michigan and the city skyline.

  • Take a picture with “The Bean”: A classic photo opportunity awaits.

Things to know:

  • Transportation: The Chicago Riverwalk is easily accessible by public transportation.

  • Magnificent Mile: Explore this iconic street for its architecture, shopping, and dining opportunities.

  • Things to do:

    • Deep dish pizza: Take advantage of the “Chicago Pizza” experience at Lou Malnati’s, a local favorite.

  • Stay:

    • Millennium Park: Enjoy the vibrant atmosphere and diverse attractions of this urban oasis.

Bonus:

  • Things to Do in Chicago:

    • Museum Hopping: The city boasts world-class museums like the Field Museum, Museum of Science and Industry, Museum of Contemporary Art, and the Art Institute.

  • Unique Experiences:

  • Chicago Riverwalk boat tour: Immerse yourself in the beauty of the city from a different perspective.

  • Second City Improv Comedy Show: Enjoy a night of laughter at this renowned comedy club.

  • Deep-dish pizza: A Chicago classic, try a deep dish pizza from: * Lou Malnati’s: For a traditional experience * Pequod’s Pizza: Known for its caramelized crust and delicious toppings.

    • Other things to do:
      • Explore the Lincoln Park Zoo: Enjoy a free visit to this urban zoo and see animals from around the world.

  • Comedy shows: Chicago is known for its improv comedy scene. Consider checking out a show at Second City, Zanies Comedy Club, or other venues for a truly unique experience.

Day 1 & 2:

  • Explore Millennium Park: Stroll along the paths, enjoy the public art, and maybe even catch a free concert or event in the park.

Enjoy the view from the Skydeck:

  • The Willis Tower (formerly Sears Tower) has a breathtaking view of Chicago from its observation deck.
  • Visit the Art Institute’s website: Check their website for current hours and ticket information, as well as information on special exhibitions and events.

Important Notes:

  • Deep-Dish Pizza:

    • Remember that “deep dish” pizza is a very deep and cheesy dish, so be prepared for a hearty meal!

    • Chicago’s architecture:

      • Chicago is known for its stunning architecture. Take a walk through the Loop and admire the skyscrapers, or explore the charming buildings in neighborhoods like Lincoln Park.

  • The Bean: Be sure to check their website for “Chicago Pizza”

Enjoy the variety of experiences Chicago has to offer!