Chicago 3 Day Itinerary

Day 1: Explore Downtown Chicago

Morning

  • Start at Millennium Park: Take a stroll through this iconic park and snap photos in front of the “Cloud Gate” sculpture (also known as “The Bean”).
  • Walk to the nearby Art Institute of Chicago: Spend a few hours exploring the impressive art collection, including works by famous American artists like Grant Wood and Thomas Hart Benton.

Afternoon

  • Take an architecture river cruise: Learn about Chicago’s rich architectural history on a guided boat tour along the Chicago River.
  • Visit the Willis Tower (formerly Sears Tower): Take in panoramic views of the city from the Skydeck on the 103rd floor.

Evening

  • Dine at Lou Mitchell’s: This beloved institution has been serving up classic American comfort food since 1923. Try their signature waffles and eggs.
  • Stay at the Kimpton Hotel Monaco Chicago: This stylish boutique hotel is located in the heart of downtown, with comfortable rooms and a rooftop bar offering great city views.

Transportation

  • Take advantage of Chicago’s comprehensive public transportation system, including buses and “L” trains (elevated trains).
  • Use ride-sharing services like Uber or Lyft to get around.

Tips

  • Be prepared for crowds and long lines at popular attractions.
  • Take breaks to enjoy the city’s many parks and green spaces.

Day 2: Explore Neighborhoods

Morning

  • Head to Wicker Park: This trendy neighborhood is known for its vintage shops, record stores, and independent coffee houses. Grab a coffee at Intelligentsia Coffee.
  • Visit the Ukrainian Institute of Modern Art: Discover an eclectic collection of contemporary art from Ukraine and around the world.

Afternoon

  • Walk through Lincoln Park: Stroll along the lakefront path and visit the Lincoln Park Zoo, which offers free admission.
  • Explore the Armitage Avenue shopping district: Find unique boutiques, antique shops, and artisanal food stores in this charming neighborhood.

Evening

  • Dine at Girl & the Goat: Celebrity chef Stephanie Izard’s Mediterranean-inspired restaurant is a must-visit for foodies.
  • Enjoy live music at the Green Mill Jazz Club: This historic club has hosted legendary jazz performers since 1907.

Transportation

  • Use public transportation or ride-sharing services to get between neighborhoods.

Tips

  • Be mindful of neighborhood boundaries and safety guidelines.
  • Take advantage of free museum days, like Tuesday evenings at the Art Institute of Chicago.

Day 3: Lakefront Fun

Morning

  • Visit Navy Pier: This lakefront attraction offers boat cruises, an amusement park, and entertainment options like the Chicago Shakespeare Theater.
  • Take a stroll along the Lake Michigan shoreline: Enjoy the scenic views and stop at the Polk Bros Park, which features public art installations.

Afternoon

  • Rent a bike and ride the Lakefront Trail: Explore the city’s scenic lakefront path, which stretches from North Avenue Beach to Navy Pier.
  • Visit the Museum of Contemporary Art: Discover an impressive collection of modern and contemporary art.

Evening

  • Dine at Alinea: For a unique culinary experience, try this Michelin three-star restaurant known for its avant-garde cuisine.
  • End your trip with fireworks at Navy Pier: Catch a free fireworks display on Wednesday evenings during the summer months.

Transportation

  • Use public transportation or ride-sharing services to get around.
  • Consider purchasing a Ventra Card for convenient travel on buses and trains.

Tips

  • Be prepared for variable Midwestern weather.
  • Take advantage of Chicago’s many free attractions and events, like outdoor concerts and movies in the park.