Chicago 4 Day Itinerary

Chicago 4-Day Itinerary

Day 1: Explore Downtown & The Loop

• Morning: Start with a hearty breakfast at Amy’s Café & Bookstore before embarking on your exploration of downtown Chicago.
• Visit Millennium Park and take a picture by the famous “Cloud Gate” sculpture (affectionately known as “The Bean”).
• Head to Navy Pier for a stroll along the lakefront, visit the Chicago Children’s Museum, or enjoy a cruise on Lake Michigan.
• Afternoon: Explore the Art Institute of Chicago (artic.edu), one of the oldest and largest art museums in the United States.
• Evening: Dine at Girl & The Goat for innovative small plates with global influences.
• Night: Catch a comedy show at Second City or a live music performance at Jazz Showcase.

Day 2: Museum Campus & The Magnificent Mile

• Morning: Fuel up with breakfast at Eggsperience Cafe before heading to the Museum Campus.
• Visit The Field Museum, Shedd Aquarium, and Adler Planetarium - all three are must-sees!
• Afternoon: Spend the afternoon shopping along The Magnificent Mile on North Michigan Avenue. Don’t forget to visit iconic stores like Macy’s, Bloomingdale’s, and Tiffany & Co.
• Evening: Enjoy dinner at RPM Italian for contemporary Italian dishes in a sophisticated setting.
• Night: Take in the city skyline from 360 CHICAGO or Willis Tower Skydeck - both offer stunning views after dark!

Day 3: Lincoln Park & Lakeview Neighborhoods

• Morning: Grab breakfast at Ann Sather’s Bakery and head to Lincoln Park.
• Visit the Lincoln Park Zoo, one of the oldest zoos in North America with free admission!
• Afternoon: Explore the beautiful grounds of Lincoln Park Conservatory and stroll along Lake Shore Drive.
• Evening: Dine at Alinea, one of the world’s most renowned restaurants, offering a unique and unforgettable dining experience.
• Night: Catch a performance by a local improv group or comedy show at iO Theater or The Second City Training Center.

Day 4: Wander the Neighborhoods

• Morning: Start with breakfast at The Bongo Room before exploring the vibrant neighborhoods of Wicker Park, Bucktown, or Logan Square.
• Visit art galleries, unique boutiques, and vintage shops in these trendy areas. Don’t forget to check out the iconic The Wicker Park Bucktown Mural.
• Afternoon: Explore the city’s street art scene by joining a guided graffiti tour, such as those offered by Chicago Graffiti & Street Art Tours.
• Evening: Enjoy dinner at Au Cheval - consistently ranked one of the best burgers in America.
• Night: End your trip with a nightcap at The Violet Hour, known for its craft cocktails and speakeasy atmosphere.

Things to Know:

• Chicago’s public transportation system, the CTA, offers an extensive network of buses and trains that make getting around easy and affordable. Invest in a Ventra Card for contactless travel.
• During summer months (June - August), be aware of increased crowds and traffic due to tourists and events like Lollapalooza and the Taste of Chicago.
• Always check the local COVID-19 guidelines before traveling, and consider purchasing tickets in advance for popular attractions to secure your spot.
• Embrace the local culture by trying deep-dish pizza from Lou Malnati’s or Giordano’s, and don’t forget to sample Chicago-style hot dogs!

Enjoy your trip to Chicago, and remember to take in the unique energy of this vibrant city!