Chicago, USA-4-day-itinerary

Day 1: Millennium Park and the Loop

Morning

  • 9:00 AM: Start your day at Millennium Park, one of Chicago’s most popular attractions.
    • Take a stroll through the beautiful Lurie Garden and visit the iconic “Cloud Gate” sculpture (also known as “The Bean”).
  • 10:30 AM: Walk to the nearby Art Institute of Chicago, one of the largest and most visited art museums in the country.
    • Spend a few hours exploring the museum’s extensive collection, which includes works by famous artists such as Monet, Picasso, and Warhol.

Lunch

  • 12:30 PM: Grab lunch at Lou Mitchell’s, a classic American diner that’s been serving up delicious breakfast and lunch dishes since 1923.
    • Try their signature dish, the “Lou Mitchell’s Burger,” which features a juicy patty topped with cheddar cheese, bacon, and caramelized onions.

Afternoon

Dinner

  • 6:00 PM: Enjoy dinner at Girl & the Goat, a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.
    • Try their signature dish, the “Wood-Fired Octopus,” which features tender octopus cooked to perfection.

Night

  • 9:00 PM: End your day with a show at Second City, one of Chicago’s most famous comedy clubs.
    • Catch a performance by one of the club’s talented comedians, or take a improv class if you’re feeling adventurous!

Day 2: The Magnificent Mile and Navy Pier

Morning

  • 9:00 AM: Start your day on the Magnificent Mile, one of Chicago’s most famous shopping districts.
    • Visit the iconic Water Tower Place mall, which features a variety of high-end retailers and restaurants.

Lunch

  • 12:00 PM: Grab lunch at Billy Goat Tavern, a classic American restaurant that’s been serving up delicious burgers and sandwiches since 1963.
    • Try their famous “Cheezborger,” which features a juicy patty topped with cheese, lettuce, tomato, and all the fixin’s.

Afternoon

  • 2:00 PM: Visit Navy Pier, one of Chicago’s most popular attractions.
    • Take a ride on the famous Centennial Wheel for stunning views of the city skyline.

Dinner

  • 6:00 PM: Enjoy dinner at The Purple Pig, a Mediterranean-inspired restaurant from Top Chef winner Bill Granger.
    • Try their signature dish, the “Porchetta,” which features tender pork cooked to perfection.

Night

  • 9:00 PM: End your day with a show at Chicago Shakespeare Theater, one of the city’s most famous theater companies.
    • Catch a performance by one of the company’s talented actors, or take a behind-the-scenes tour if you’re feeling adventurous!

Day 3: Wicker Park and Bucktown

Morning

  • 9:00 AM: Start your day in Wicker Park, one of Chicago’s trendiest neighborhoods.

Lunch

  • 12:00 PM: Grab lunch at Big Star, a retro-style diner that serves up delicious burgers and sandwiches.
    • Try their signature dish, the “Big Star Burger,” which features a juicy patty topped with cheese, bacon, and caramelized onions.

Afternoon

  • 2:00 PM: Visit The 606, an elevated park that runs through several of Chicago’s trendy neighborhoods.
    • Take a stroll along the park’s many public art installations and enjoy the city views.

Dinner

  • 6:00 PM: Enjoy dinner at Au Cheval, one of Chicago’s most famous restaurants.
    • Try their signature dish, the “Cheeseburger,” which features a juicy patty topped with cheese, lettuce, tomato, and all the fixin’s.

Night

  • 9:00 PM: End your day with a show at Thalia Hall, one of Chicago’s most famous music venues.
    • Catch a performance by one of the venue’s talented musicians, or take a behind-the-scenes tour if you’re feeling adventurous!

Day 4: Lincoln Park and North Side

Morning

  • 9:00 AM: Start your day in Lincoln Park, one of Chicago’s most popular neighborhoods.
    • Visit the iconic Lincoln Park Zoo to see some of the city’s best local wildlife.

Lunch

  • 12:00 PM: Grab lunch at The Gage, a modern American restaurant that serves up delicious burgers and sandwiches.
    • Try their signature dish, the “Gage Burger,” which features a juicy patty topped with cheese, bacon, and caramelized onions.

Afternoon

  • 2:00 PM: Visit North Avenue Beach, one of Chicago’s most famous beaches.
    • Take a stroll along the beach and enjoy the city views.

Dinner

  • 6:00 PM: Enjoy dinner at Alinea, one of Chicago’s most famous restaurants.
    • Try their signature dish, the “Alinea Experience,” which features a variety of unique and innovative courses.

Night

  • 9:00 PM: End your day with a show at The Vic Theatre, one of Chicago’s most famous music venues.
    • Catch a performance by one of the venue’s talented musicians, or take a behind-the-scenes tour if you’re feeling adventurous!

Things to Know:

  • Weather: Chicago has a humid continental climate with cold winters and hot summers. Be sure to pack accordingly!

  • Transportation: Chicago has a comprehensive public transportation system that includes buses, trains, and the “L” (elevated train). You can use the Ventra card or buy individual tickets.

  • Tips:

    • Be prepared for crowds and lines at popular attractions.
    • Don’t eat at touristy restaurants – try some of the city’s best local spots instead!
    • Take a stroll along the Lake Michigan shoreline for beautiful views of the city skyline.

Where to Stay:

  • The Langham Chicago: A luxurious hotel located in the heart of the city.
  • The Four Seasons Hotel Chicago: A high-end hotel with stunning views of the lake.
  • The Hotel Lincoln: A boutique hotel with a vintage vibe and great location.

Other Tips and Recommendations:

  • Try some of the city’s best local foods: Deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs are must-try dishes!
  • Visit some of the city’s famous museums: The Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry are all world-class institutions.
  • Take a stroll along the Magnificent Mile: This iconic shopping district is home to some of the city’s best high-end retailers.