Search Chicago Holiday Homes from AU$143

Depending on when you visit, you can score a holiday home in Chicago for as little as AU$143 per night. Prices vary by property class, amenities, and location, all of which you can quickly sort through on our handy search page.

Discover exclusive deals on Chicago house rentals when you book with Wotif. Once you enter the dates of your trip and number of travellers (Girls’ trip? Family getaway? We’ve got you covered.), filter the results by guest rating, budget, property class, number of bedrooms, amenities, and more. You can also use the map feature to zoom in on the neighbourhood or to view several rentals at once.

Because there’s nothing better than having a private place to call your home away from home while exploring Chicago. When you book a holiday house in Chicago, you can indulge in a variety of sweet amenities and truly relax in your own space.

Pack your bags and head to your rental house in , the most popular time to visit. If smaller crowds are your thing, book a holiday home in the off-season, around , when you may get more of a bargain.

Whether you’re adventuring to Chicago for the first time or planning a return trip to your favourite spot, pick from 822 unique holiday homes in Chicago.

You’ll often find most amenities you’re looking for, such as a private pool or hot tub, parking on the premises, a full-service kitchen or kitchenette, laundry and Wi-Fi. If your companion has four legs, book a pet-friendly Chicago accommodation so your furry pal is as comfy and cosy as can be. Keep in mind that the price of your rental will depend on how luxe the amenities are.

You’ll find spectacular deals, book now and pay later discounts, and a massive inventory of one-of-a-kind house rentals. Save big bucks when you book your Chicago car hire and accommodation together into a Chicago holiday package. Our Price Promise means that if you find a lower price online up to 24 hours before check-in, we’ll match it and refund the difference. Do the right thing and book your Chicago holiday house with Wotif.

We understand that plans change, so we offer thousands of holiday homes that have free cancellations. To be sure your rental can be cancelled for a full refund, filter your search by “free cancellation”. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.