From skyscrapers to museums to vibrant neighborhoods to public parks, Chicago has something for everyone, and three days is more than enough time to explore its highlights. Travel by bus, bike, or on foot; linger in the bustling Loop; or head out of town on a day trip. Here’s how to plan your 3-day Windy City itinerary.
Day 1: Chicago’s Top Attractions
Explore Chicago’s most popular landmarks, many of which are concentrated in the Loop neighborhood, including Millenium Park and the Willis Tower Skydeck. Bus and bicycle tours of the area make it possible to see more in less time, while a hop-on hop-off bus itinerary offers a seamless overview of the city (plus the chance to disembark where and when you wish). Alternatively, combine your Loop adventures with a trip to another part of town. Catch an afternoon Cubs game at Wrigley Field on the North Side, or head to the South Side to explore Chinatown.
Day 2: Museums, Architecture, and Other Historical Highlights
Learn about Chicago’s past on an architecture tour—hop aboard a riverboat and cruise all three branches of the Chicago River, spotting highlights such as the Tribute Tower and the Merchandise Mart as you go, or head off on an intimate walking tour to view landmarks firsthand. Then, delve into Chicago’s esteemed museums, including the Field Museum of Natural History, Museum of Science and Industry, and the Art Institute of Chicago.
Day 3: Chicago Area Day Trip
Frank Lloyd Wright, a longtime Chicago resident and one of the 20th century’s most celebrated architects, designed a number of buildings in the Chicago area. Discover some of his best-known works on a day trip to the Frank Lloyd Wright Home and Studio in Oak Park, a village located just beyond Chicago’s western edge. Here you'll discover where the architect lived and worked for the first two decades of his career, and where he developed his signature Prairie School style. Oak Park’s other architectural gems include the Frank Lloyd Wright Historic District, Unity Temple, and the Arthur B. Heurtley House.