Like beacons rising from the plains of the American Midwest, the skyscrapers of Chicago tower over the nation's third-largest city. Home to 26 miles of lakeshore and more world-class restaurants than there is time to count, the Windy City draws tens of millions of visitors to its streets each year. Whether you're a business traveler, a food lover, or a baseball fanatic, you'll find a home away from home in our Chicago luxury vacation rentals.
With boundaries that stretch across 237 square miles, Chicago is best approached as a collection of neighborhoods - 77 to be exact, each with its own distinct character.
Within downtown Chicago, you can wander through a maze of skyscrapers in The Loop (named for the "L" tracks that encircle it) and find endless opportunities to shop on Michigan Avenue's Magnificent Mile. Head northward to join the throngs of Cubs fans in Wrigleyville, enjoy Lake Michigan's sandy shores in Lakeview, spend a day boutique shopping in Wicker Park, and graze in the green spaces of Lincoln Park. If make your way south, you'll find the prestigious University of Chicago in Hyde Park and the wide public beaches that line the South Shore.
In a city with more than 200 theaters and 15 miles of swimming beaches, guests at our Chicago vacation homes will find no shortage of year-round activities.
Take a ride on the L to survey the scene around The Loop, and stand at the base of the 110-story Willis Tower to gaze at the tallest building in the Western Hemisphere. Hop on board an architectural boat tour of the Chicago River, spend a rainy day touring the Art Institute of Chicago or the Museum of Science and Industry, and catch at least one home game in the stands at Wrigley Field.
The famed Lincoln Park Zoo is the oldest public zoo in the United States, and is one of only three to offer free admission. You can also rent bikes to ride on more than 19 miles of lakefront bike paths, pack a picnic for lunch alongside "The Bean" in Millennium Park, and catch an evening performance at The Second City, the Chicago Theatre, Jazz Showcase, or Green Mill.
Whether it's summer or winter, for business or pleasure, our Chicago vacation rentals will show you the best of the Windy City!