Chicago, Illinois 2 Day Itinerary

Chicago 2-Day Itinerary

Day 1:

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

  • Willis Tower (Sears Tower): Start your day with panoramic views of the city from the Skydeck on the 103rd floor. ($22 per person)
  • The Loop: Take a stroll through this vibrant neighborhood and grab a coffee at one of the many cafes.

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

  • Millennium Park: Explore iconic landmarks like the “Cloud Gate” sculpture (also known as “The Bean”) and take in a free outdoor concert or festival if scheduled.
  • Art Institute of Chicago: Spend a few hours exploring one of the top art museums in the country. ($20 per person)

Evening (4:00 pm - 9:00 pm)

  • Navy Pier: Take a sunset cruise on Lake Michigan or enjoy dinner at one of the many restaurants with lake views.
  • The Signature Room at the 95th: Treat yourself to upscale dining and stunning city views. ($$$$)

Day 2:

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

  • Lincoln Park Zoo: Visit the historic zoo, which offers free admission and is home to over 1,100 animals.
  • North Avenue Beach: Take a leisurely walk along the lakefront path or rent a bike and ride along the shoreline.

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

  • Wrigley Field: Catch a Cubs game at this historic baseball stadium. ($20-$50 per person)
  • The Magnificent Mile: Shop and dine along Michigan Avenue, lined with high-end boutiques and restaurants.

Evening (4:00 pm - 9:00 pm)

  • Chicago Riverwalk: Take a romantic stroll along the river and enjoy dinner at one of the many eateries.
  • Girl & the Goat: Savor Mediterranean-inspired cuisine from Top Chef winner Stephanie Izard. ($$$)

Where to Stay:

  • The Langham Chicago: Luxuriate in this 5-star hotel’s elegant rooms and world-class service. ($$$$)
  • Hyatt Centric The Loop Chicago: Enjoy modern amenities and a convenient location in the heart of downtown. ($$)

Transportation:

  • ‘L’ Train (Elevated Train): Use the convenient and affordable ‘L’ train to get around the city.
  • Ride-hailing Apps: Uber and Lyft are widely available in Chicago.

Tips and Essentials:

  • Weather: Pack layers for unpredictable Midwestern weather, with cold winters and hot summers.
  • Comfortable Shoes: Be prepared for walking, as many attractions are within walking distance or require a short bus ride.
  • Tipping: 15%-20% is standard for good service at restaurants and bars.

Other Things to Know:

  • Chicago-style Hot Dogs: Try a classic hot dog with relish, onions, tomatoes, sport peppers, and celery salt at Portillo’s or Alinea.
  • Deep-dish Pizza: Savor a thick-crust pizza at Lou Malnati’s, Pequod’s, or Gino’s East.
  • Free Attractions: Take advantage of free admission to many museums and attractions on certain days of the week or month.

Additional Resources: