Explore 2577 vacation rentals near Chicago, Illinois. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Chicago, you can see photos of Chicago vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Chicago vacation rentals in specific areas. Whether you’re looking for a Chicago staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Chicago is per night and the highest price is per night.
To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
1044 available
2 bed rentals
676 available
3 bed rentals
370 available
4+ bed rentals
225 available