Chicago-7-day-itinerary

Day 1: Monday

  • Morning: Start your day at Millennium Park to see the famous “Cloud Gate” sculpture (aka “The Bean”) and take some iconic photos.
  • Lunch: Grab a classic Chicago-style hot dog from Portillo’s.
  • Afternoon: Visit the Art Institute of Chicago to see some of the world’s most famous artworks, including American Gothic and Nighthawks.
  • Evening: Head to The Magnificent Mile for shopping and people-watching.
  • Where to Stay: Consider staying at the The Langham Chicago, a luxurious hotel with great views of the city.

Day 2: Tuesday

  • Morning: Take an architectural river cruise to see some of Chicago’s most famous buildings, including the Willis Tower and Tribune Tower.
  • Lunch: Try some deep-dish pizza at Lou Malnati’s.
  • Afternoon: Visit the Field Museum to see Sue, the largest T-Rex skeleton ever found.
  • Evening: Catch a show or concert at one of Chicago’s many world-class theaters, such as the Chicago Theatre.
  • Tips:
    • Be sure to book your river cruise and theater tickets in advance, especially during peak season.

Day 3: Wednesday

  • Morning: Explore the trendy neighborhood of Wicker Park, known for its vintage shops and street art.
  • Lunch: Grab a coffee and pastry at Intelligentsia Coffee.
  • Afternoon: Visit the National Museum of Mexican Art to learn about the rich history and culture of Mexico.
  • Evening: Head to Logan Square for dinner and drinks at one of its many hip restaurants and bars.

Day 4: Thursday

  • Morning: Visit the historic Wrigley Field to take a guided tour.
  • Lunch: Try some classic Chicago-style burgers at Au Cheval.
  • Afternoon: Explore the beautiful Lincoln Park Conservatory, a stunning glass conservatory with tropical plants.
  • Evening: Catch a Cubs game at Wrigley Field if there’s a home game scheduled.

Day 5: Friday

Day 6: Saturday

  • Morning: Visit the iconic Willis Tower (formerly Sears Tower), which offers panoramic views of the city from its Skydeck on the 103rd floor.
  • Lunch: Try some artisanal ice cream at Black Dog Gelato.
  • Afternoon: Explore the trendy neighborhood of Pilsen, known for its vibrant street art and Mexican cuisine.
  • Evening: Catch a comedy show or improv performance at one of Chicago’s many comedy clubs, such as The Second City.

Day 7: Sunday

  • Morning: Take a scenic bike ride along the Lakefront Trail.
  • Lunch: Grab some brunch at The Purple Pig, a Michelin-starred restaurant with creative small plates.
  • Afternoon: Visit the historic Armstrong Park to see the famous Chicago Shakespeare Theater and take a stroll through the beautiful gardens.
  • Evening: End your trip with a dinner at one of Chicago’s many world-class restaurants, such as Alinea.

Things to Know:

  • Be prepared for crowds and long lines during peak season (June-August).
  • Try to avoid traveling during rush hour (7-9 am and 4-6 pm) to minimize traffic congestion.
  • Don’t forget to try some of Chicago’s famous desserts, such as deep-dish pizza or a classic Italian beef sandwich with giardiniera.

Transportation:

  • The easiest way to get around the city is by using public transportation, including buses and the ‘L’ (elevated train).
  • Consider purchasing an Ventra Visitor Pass for unlimited rides on buses and trains.
  • Taxis and ride-sharing services are also widely available.

Tips:

  • Be sure to try some of Chicago’s famous street food, such as hot dogs or Italian beef sandwiches with giardiniera.
  • Don’t miss the beautiful Millennium Park at night, when it’s lit up with colorful lights and music.
  • Consider purchasing a Chicago CityPASS for discounts on popular attractions like the Willis Tower and Art Institute of Chicago.

Other Things to Do:

  • Visit the Lincoln Park Zoo, a free zoo located in Lincoln Park.
  • Take a scenic boat tour of Lake Michigan and see some of the city’s most iconic landmarks from the water.
  • Explore the trendy neighborhood of Bucktown, known for its vintage shops, street art, and hip restaurants.