Chicago 3 Day Itinerary

Day 1: Exploring Downtown Chicago

  • Morning:

    • Start your day with breakfast at The Original Pancake House, known for its giant pancakes and unique varieties. (240 E Pearson St, Chicago, IL 60611)
    • Visit the Willis Tower (233 S Wacker Dr, Chicago, IL 60606). Take the Skydeck to enjoy panoramic views of the city from the 103rd floor.

  • Afternoon:

    • Head to Millennium Park (20 N Upper Wacker Dr, Chicago, IL 60606) to see the iconic Cloud Gate sculpture (also known as “The Bean”).
    • Explore Navy Pier (600 E Grand Ave, Chicago, IL 60611). Visit the Chicago Children’s Museum or the Smith Museum of Stained Glass Windows. Take a cruise on Lake Michigan with Wendella Sightseeing.

  • Evening:

    • Dine at Girl & The Goat (809 W Randolph St, Chicago, IL 60607), a popular spot for innovative small plates. Make sure to book in advance!
    • End your day with a walk along the Magnificent Mile (N Michigan Ave, Chicago, IL 60611) and enjoy the city lights.

Day 2: Discovering Museums and Neighborhoods

  • Morning:

    • Have breakfast at Ann Sather Cafe (Multiple locations, e.g., 1537 N Clybourn Ave, Chicago, IL 60610) known for its cinnamon rolls.
    • Visit the Art Institute of Chicago (111 S Michigan Ave, Chicago, IL 60603) - one of the oldest and largest art museums in the United States.

  • Afternoon:

    • Head to Lincoln Park (2045 N Stockton Dr, Chicago, IL 60614). Visit the Lincoln Park Zoo or the free art exhibits at the Alfred Caldwell Lily Pool.
    • Explore Wrigleyville and grab lunch at Mike’s Bar & Grill, a classic Chicago sports bar (3707 N Clark St, Chicago, IL 60613).

  • Evening:

    • Dine at Alinea (178 W Huron St, Chicago, IL 60654), one of the world’s best restaurants. Make sure to book well in advance!
    • Take a stroll along Lake Michigan or visit Second City Comedy Club (1616 N Wells St, Chicago, IL 60614) for an evening of laughter.

Day 3: Exploring the Architecture and Eateries of Chicago

  • Morning:

    • Start your day with breakfast at Amy’s Café & Bookstore (872 S Ashland Ave, Chicago, IL 60607).
    • Take an architecture river cruise with Chicago Architecture Center to learn about the city’s impressive skyline.

  • Afternoon:

    • Visit The Field Museum (1401 S Lake Shore Dr, Chicago, IL 60605) or Shedd Aquarium (1200 S Lake Shore Dr, Chicago, IL 60605).
    • Explore Chinatown (2300 S Archer Ave, Chicago, IL 60616) for lunch at New Chinatown Mall Food Court.

  • Evening:

    • Dine at Avec (615 W Randolph St, Chicago, IL 60661), known for its Mediterranean small plates.
    • End your trip with a visit to The Signature Room at the 95th (875 N Michigan Ave, 95th Floor, Chicago, IL 60611) for drinks and more stunning city views.

Things to Know:

  • Chicago’s public transportation system is called the CTA. Buy a Ventra card for easy travel on buses and trains.
  • Tipping in restaurants is customary: around 20% of the bill.
  • Chicago weather can be unpredictable, so pack layers!
  • Reservations are highly recommended for popular restaurants.

Transportation: Chicago’s public transportation system (CTA) offers an easy and affordable way to get around the city. Purchase a Ventra card for buses and trains, or consider the 7-day unlimited pass if you plan to explore extensively. Taxis and ride-sharing services like Uber and Lyft are also available.

Tips:

  • Explore neighborhoods like Wicker Park, Logan Square, and Pilsen for unique shops, bars, and restaurants.
  • Check out the Chicago Cultural Center’s free tours and exhibits.
  • Don’t miss a deep-dish pizza from Lou Malnati’s or Gino’s East!