Chicago Illinois 3 Day Itinerary

Chicago, Illinois: A 3-Day Itinerary

Day 1 - Exploring Downtown Chicago

Morning:

  • Start your day with breakfast at The Original Pancake House, known for its massive and delicious pancakes. (1701 N. Vermont Ave.)
  • Visit the iconic Cloudgate (The Bean) in Millennium Park and take some memorable photos.
  • Explore The Art Institute of Chicago, one of the oldest and largest art museums in the United States. (111 S. Michigan Ave.)

Afternoon:

  • Lunch at Girl & The Goat, a popular farm-to-table restaurant with innovative dishes. (809 W. Randolph St.)
  • Take a river cruise with Shoreline Sightseeing to see the city from a different perspective. (Several locations along the Chicago River)
  • Visit Navy Pier, home to various attractions, including the Centennial Wheel and the Chicago Children’s Museum.

Evening:

  • Dinner at Gibsons Bar & Steakhouse for a classic Chicago steak experience. (1028 N. Rush St.)
  • Catch a comedy show at Second City, the birthplace of many famous comedians. (1616 N. Wells St.)

Day 2 - Museums and Neighborhoods

Morning:

  • Breakfast at Ann Sather’s Bakery & Cafe for a Scandinavian-style breakfast. (Multiple locations, but Lincoln Park is a popular choice.)
  • Visit the Field Museum, home to Sue, the T. rex skeleton. (1400 S. Lake Shore Dr.)
  • Explore the Shedd Aquarium and meet the famous beluga whales and seals. (2301 S. Lake Shore Dr.)

Afternoon:

  • Lunch at Alinea, one of the world’s best restaurants, for a unique dining experience. Reservations recommended. (178 West Huron St., reservations required)
  • Head to Wrigley Field (1060 W. Addison St.) and explore the historic home of the Chicago Cubs if there’s no game.
  • Visit Lincoln Park Zoo, one of the oldest zoos in North America, free of charge. (2001 N. Clark St.)

Evening:

  • Dinner at Au Cheval, famous for its burgers and brunch menu. (800 W. Randolph St.)
  • Enjoy a jazz performance at Green Mill Cocktail Lounge, a historic jazz club. (4802 N. Broadway St.)

Day 3 - Architecture and Foodie Delights

Morning:

  • Breakfast at Lou Malnati’s Pizzeria for a classic Chicago deep-dish pizza. (Multiple locations, but the Lakeview location is popular.)
  • Take an Architecture River Cruise to learn about Chicago’s iconic buildings and skyscrapers. (Several locations along the Chicago River)

Afternoon:

  • Lunch at Frontera Grill, a restaurant by celebrity chef Rick Bayless, for authentic Mexican cuisine. (445 N. Clark St.)
  • Visit Museum of Science and Industry to explore interactive exhibits and learn about science. (5700 S. Lake Shore Dr.)

Evening:

  • Dinner at Girl & The Goat (if you didn’t go on Day 1, as it can be hard to get reservations) or try Japonais, a trendy Japanese restaurant. (59 W. Hubbard St.)
  • End your trip with a visit to The Signature Room at the 95th for stunning city views and cocktails. (John Hancock Center, 875 N. Michigan Ave., floor 95)

Things to Know:

  • Chicago is known as “The Windy City,” but it’s not because of the wind; it’s because of its political leaders who were said to be full of hot air.
  • Public transportation is easy with the CTA (Chicago Transit Authority). You can use Ventra cards for buses and the elevated trains (the “L”).
  • Tipping in restaurants is customary and generally 20% of the bill.
  • During summer, don’t miss Millennium Park’s Summer Film Series or Lakeshore Path, perfect for biking or walking.

Enjoy your trip to Chicago!