Chicago, Illinois-2-day-itinerary

Chicago, Illinois 2-Day Itinerary

Day 1:

Morning (9:00 am - 12:00 pm)

  • Start at Millennium Park: Begin your day by exploring this iconic park in the heart of downtown Chicago. Take a stroll through the beautiful Lurie Garden and snap a photo in front of the famous “Cloud Gate” sculpture (also known as “The Bean”).
  • Take a short walk to the Art Institute of Chicago: One of the top art museums in the country, with a collection that spans 5,000 years of human creativity.

Afternoon (12:00 pm - 4:00 pm)

  • Grab lunch at Portillo’s: This Chicago staple serves up delicious hot dogs, Italian beef sandwiches, and chocolate cake.
  • Take an architecture river cruise: Learn about the city’s rich history and iconic buildings on a guided 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 (5:00 pm - 10:00 pm)

  • Enjoy dinner at Girl & the Goat: Top Chef winner Stephanie Izard’s Mediterranean-inspired restaurant is a must-visit.
  • Take a stroll along the Magnificent Mile: This famous stretch of Michigan Avenue is lined with high-end boutiques, restaurants, and iconic landmarks like the Tribune Tower.

Day 2:

Morning (9:00 am - 12:00 pm)

  • Explore Lincoln Park Zoo: This free zoo in the heart of Lincoln Park is home to over 1,100 animals from around the world.
  • Visit the Peggy Notebaert Nature Museum: Discover the natural history of the Chicago region through interactive exhibits and a beautiful butterfly garden.

Afternoon (12:00 pm - 4:00 pm)

  • Grab lunch at Xoco: Rick Bayless’s casual Mexican spot serves up fresh, delicious street food-style dishes.
  • Take a walk along Navy Pier: This lakefront attraction offers stunning views of Lake Michigan and the city skyline. Catch a boat tour or ride the Ferris wheel for added fun.

Evening (5:00 pm - 10:00 pm)

  • Enjoy dinner at Au Cheval: This trendy diner is famous for its burgers, but also serves up creative takes on classic American fare.
  • Catch a show at Second City: This legendary comedy club has launched the careers of stars like Tina Fey and Stephen Colbert.

Where to Stay:

  • The Wit Hotel: A stylish, boutique hotel in the heart of River North, with chic rooms and a rooftop bar offering stunning city views.
  • The Kimpton Hotel Monaco Chicago: A luxurious, pet-friendly hotel in the Loop, with elegant rooms and a complimentary evening wine hour.

Transportation:

  • ‘L’ Train (Elevated Train): An efficient way to get around the city, with multiple lines connecting major attractions.
  • Ride-hailing services: Uber and Lyft are widely available in Chicago.
  • Walking and biking: Chicago has a walkable grid system, making it easy to explore on foot or by bike.

Tips and Insights:

  • Be prepared for wind: Chicago is known as the “Windy City,” so dress accordingly!
  • Take advantage of free attractions: Many of Chicago’s museums and parks offer free admission on certain days of the week or month.
  • Try a classic Chicago-style hot dog: With relish, onions, tomatoes, sport peppers, and celery salt, this is a culinary experience you won’t want to miss!

Other Things to Know:

  • Weather: Chicago can be quite chilly in the spring and fall, with cold winters and warm summers.
  • Safety: As with any major city, take common-sense precautions to ensure your safety, especially at night.
  • Events and festivals: Chicago hosts many world-class events throughout the year, including Lollapalooza, Pitchfork Music Festival, and the Taste of Chicago. Check the city’s event calendar to catch something special during your visit!