Chicago, IL, USA

We found 1,164 vacation rentals -- search to see all properties

Vacation Rentals in Chicago: Apartments, Condos & More


globe svg-lock svg-credit-card

Why use HomeAway?

Your perfect vacation starts here!

Choose a rental from the world's best selection.

Book and stay with confidence!

Secure payments and peace of mind.

Your vacation, your way!

More space, more privacy, no compromises.

Why Everybody Loves Visiting Chicago

The city of Chicago is one of the landmarks of United States history. With pilgrims setting in 1780 and officially establishing as a city in 1837, people have flooded to this great city for generations. It is a hub of technology, finance, and a center of civilization. People who visit will usually choose to stay in one of the five star hotels offered by the city.

The Field Museum of Natural History

People come to Chicago for the intrigue and the intellectual stimulation. The Museum of Natural History offers a host of exhibits, ranging from full-size dinosaurs with 3D animations of how that dinosaur would have behaved, to the mummies of ancient Egypt, to the mysteries and life crawling around underground. Learn about different wildlife and facets of history. Learn what scientists have discovered about our ancestors from the ruins of ancient civilizations. They even feature a free admission day every now and then. Anybody who comes to Chicago in search of education will be fulfilled at the Field Museum of Natural History.

Shedd Aquarium

There are some features of the world that many people only get to read about. They will only get to see pictures of it. Marine life is much like that. Many of us do not have the opportunity to see the unique wildlife that lives deep in the sea. But at the Shedd Aquarium, visitors to Chicago have that opportunity. People are invited to come and witness the beautiful and yet intriguing species of marine life that they would otherwise never have the opportunity to do. They even make an effort to preserve endangered species in their aquarium.

The Art Institute of Chicago

Downtown Chicago has been long known for its indulgence in artistic endeavors. Art is the oldest form of expression, found in ancient civilizations, expressing the opinions and beliefs of different epochs. Art is critical to understanding the thoughts of civilizations of the past. Much of what we know about the Grecians emanates from their love of art. Much of the great artwork of history is preserved in the Art Institute of Chicago. If you want to learn about the Byzantine era, Van Gogh, or the ancient Egyptians, you should pay them a visit.

Transit Nightclub

When you have exhausted your intellectual energy for the day, you might consider the vast options of nightlife that the city of Chicago offers by the Chicago River. The Transit Nightclub is the perfect place to unwind and to meet some of the Chicago locals. It has five bars and a massive dance floor. This will provide ample opportunity to go and mingle with people and to make new friends. It also has lounge seating for when you just want to sit down and relax, and optimal lighting to accommodate your night life.


People are usually advised to visit Chicago in the Spring or in the Fall. The temperature is not too warm (between 55°F and 70°F) and there is plenty to do during that time. There are a lot of festivals and lower hotel rates. Chicago is packed in the summer months and the heat can be brutal.

How To Get There

When visiting the Windy City, people are confronted with how they are going to get around. The primary option is usually to just rent a car. However, Chicago also has a highly developed public transit system. The train is usually very convenient. The Pace bus system also serves the city and surrounding areas.