Top Chicago Tours & Day Trips

Chicago is one of the most exciting and architecturally impressive cities in the United States, known for its world famous skyline, deep cultural history, lakefront parks and friendly neighbourhoods. This hub collects the best tours, attractions and activities around Chicago so you can easily understand what the city offers and plan the experiences that match your visit. Whether you want to explore the river, try local food, see the museums or discover the history behind Chicago's iconic buildings, this page gives you a simple and helpful starting point.

Many visitors begin with a Chicago River architecture cruise, one of the city's signature experiences and the best way to learn about its famous skyscrapers and design heritage. Walking tours of the Loop, Millennium Park and the lakefront are also popular, giving you a close look at Cloud Gate, the Art Institute of Chicago, historic buildings and public art. Hop on hop off bus tours provide an easy overview of the main districts, including Navy Pier, Magnificent Mile, Grant Park, Museum Campus and Lincoln Park.

Chicago is also known for its food culture, and tasting tours let you try local favourites such as deep dish pizza, hot dogs, Italian beef and classic neighbourhood dishes. For something different, you can join Chicago gangster and crime themed tours, bike rides along the lakefront, river kayaking or cultural experiences that take you through artistic areas like Wicker Park, Pilsen and Chinatown. Families often enjoy visits to Shedd Aquarium, Field Museum or the Skydeck at Willis Tower for panoramic city views.

Beyond the city itself, Chicago offers a range of day trips to the surrounding region. Popular options include excursions to nearby state parks, Lake Michigan beaches, historical small towns and scenic nature areas in Illinois, Wisconsin and Indiana. These trips are ideal if you want to experience a quieter side of the Midwest during your visit.

Each category below explains what to expect from different types of tours and links to detailed comparison pages where you can check real time prices, inclusions and schedules from trusted providers. Use this guide to discover the best things to do in Chicago and choose experiences that fit your time, interests and travel style. Our goal is to make planning easy, clear and reliable so you can enjoy the best of the Windy City.