Multi-day Trips Chicago

Multi-Day Trips in Chicago

Overview

Experience the vibrant city of Chicago over several days and explore its rich history, architecture, culture, and cuisine! Here’s a suggested itinerary to help you make the most of your multi-day adventure.

Day 1: Downtown Exploration

The Loop

Start your journey in The Loop, home to iconic buildings like Willis Tower (Sears Tower) and Millennium Park, where you can find the famous “Bean” sculpture (Cloud Gate). Take a skydeck tour for breathtaking views of the city.

Head north to Navy Pier, enjoy a ride on the Centennial Wheel or visit the Chicago Children’s Museum. Don’t forget to stroll along the lakefront and grab a bite at one of the pier’s many eateries.

Day 2: Museums & Architecture

Museum Campus

Spend the day at Museum Campus home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Explore the permanent and temporary exhibits these world-class institutions have to offer.

Chicago River Architecture Tour

In the afternoon, take a Chicago River Architecture Cruise to learn about the city’s landmark buildings from Frank Lloyd Wright to Mies van der Rohe.

Day 3: Neighborhood Exploration

Wrigleyville & Wicker Park/Bucktown

Visit Wrigleyville home of Wrigley Field, where you can take a tour or catch a Cubs game if they’re in season. Then head to Wicker Park and Bucktown neighborhoods known for their vibrant arts scene, independent shops, and delicious dining options.

Day 4: Lincoln Park & Lakeshore

Lincoln Park Zoo & Lincoln Park Conservatory

Start your day at the historic Lincoln Park Zoo, then visit the stunning Lincoln Park Conservatory.

North Avenue Beach & Lincoln Park

Relax at North Avenue Beach and soak up the sun, or try out water sports like kayaking or paddleboarding. In the evening, grab dinner at one of the restaurants in nearby Linden Ave.

Tips

  1. Consider getting a Chicago CityPASS, which provides discounted admission to several popular attractions.
  2. Use public transportation like the CTA (Chicago Transit Authority) to navigate the city easily and affordably.
  3. Check local events listings for concerts, festivals, or shows happening during your visit.
  4. Dress in layers as temperatures can vary throughout the day and between different parts of the city.