Chicago, Illinois-3-day-itinerary

Chicago: 3-Day Itinerary

Where To Stay:

  • Budget: Hostelling International Chicago, The Freehand Chicago
  • Mid-Range: Hotel EMC2, Autograph Collection, The Robey
  • Luxury: The Peninsula Chicago, Four Seasons Hotel Chicago

Transportation:

  • CTA (Chicago Transit Authority): Extensive network of trains and buses, affordable and efficient. Purchase a Ventra Card for easy fare payment.
  • Divvy Bikes: Bike-sharing program with stations throughout the city. Perfect for exploring neighborhoods.
  • Walking: Chicago is very walkable, especially downtown.

Things To Know:

  • Chicago weather can be unpredictable. Pack layers and be prepared for all types of conditions.
  • Tipping is customary in restaurants and bars (15-20% of the bill).
  • Deep dish pizza is a Chicago staple – try it!
  • Be aware of your surroundings, especially at night.

Day 1: Downtown Delights

Morning:

  • Millennium Park: Explore Cloud Gate (“The Bean”), Crown Fountain, and Lurie Garden. Free admission.
  • Art Institute of Chicago: World-renowned art museum with iconic works like Grant Wood’s “American Gothic.” Allow at least 2-3 hours. (Entry fee)

Afternoon:

  • Lunch: Grab a classic Chicago hot dog at Portillo’s Hot Dogs.
  • Skydeck Chicago: Ascend Willis Tower for breathtaking panoramic views of the city. (Entry fee)

Evening:

  • Dinner: Enjoy a fine dining experience at RPM Steak or a more casual meal at Au Cheval.
  • Theatre District: Catch a Broadway show in the vibrant Theatre District.

Day 2: Culture and Cuisine

Morning:

  • Museum of Science and Industry: Interactive exhibits exploring science, technology, and engineering. (Entry fee)
  • Lunch: Savor authentic Mexican cuisine at Taqueria El Milagro.

Afternoon:

  • Wicker Park/Bucktown: Explore these trendy neighborhoods with independent boutiques, art galleries, and cafes.

Evening:

  • Dinner: Indulge in deep dish pizza at Lou Malnati’s Pizzeria or Pequod’s Pizza.
  • Chicago Blues: Experience the city’s legendary blues scene at Kingston Mines or Buddy Guy’s Legends.

Day 3: Neighborhood Exploration & Relaxation

Morning:

  • Lincoln Park Zoo: Enjoy a free visit to this world-class zoo with diverse animal exhibits.
  • Lunch: Grab a delicious sandwich from D’Agostino’s on Armitage Avenue in Lincoln Park.

Afternoon:

  • Lakefront Trail: Rent a bike and explore the scenic Lakefront Trail, offering stunning views of Lake Michigan.
  • Navy Pier: Take a ride on the Ferris wheel, enjoy street performers, and browse the shops at this popular tourist destination.

Evening:

  • Dinner: Savor Italian cuisine with lake views at Riva Crab House.
  • Farewell Drinks: Enjoy cocktails at The Signature Room at the 95th floor for breathtaking city views.

Other Points of Interest:

  • Wrigley Field (home of the Chicago Cubs)
  • Magnificent Mile (luxury shopping street)
  • Garfield Park Conservatory
  • Museum of Contemporary Art Chicago
  • Shedd Aquarium

Tips:

  • Purchase a CityPASS for discounted admission to several attractions.
  • Take advantage of free events and festivals throughout the year.
  • Check out Time Out Chicago for current recommendations on restaurants, bars, and events.
  • Don’t be afraid to ask locals for their favorite spots!