Chicago vacation rentals

The average price for a weekly Chicago vacation rental found by KAYAK users in the last 2 weeks is $1,750.

The average price for a monthly Chicago vacation rental found by KAYAK users in the last 2 weeks is $7,501.

There are loads of different property types that you can make your vacation home in Chicago. You’ll find apartments, bungalows, cabins, campgrounds, caravan parks, chalets, condos, cottages, houses, holiday parks, homestays, lodges and villas.

There are many types of properties available for Chicago vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Wicker Park Chicago and Entire Modern 2 Bedroom Apartment.

If you’re a large group then you’ll need plenty of space. The highest rated vacation homes that can sleep 6 people or more by KAYAK users are Forrestville Ave Large Suite and Entire Modern 2 Bedroom Apartment.

There are a number of dog and pet-friendly Chicago vacation rentals, with around 16% allowing you to bring your pet along with you.

KAYAK users have found vacation rentals in Chicago for as cheap as $107 in the last 3 days. The average price is $250.

In the last 72 hours, users have found Chicago vacation rentals for tonight for as low as $96. Search here for similar prices

Vacation rentals in Near North Side, Lake View and Near West Side have the most searches on KAYAK. For more information about Chicago's different neighborhoods, check out our Chicago's City Guide.

Take a look at our vacation rentals map to find the best vacation rental homes near you.

If you enjoy physical fitness and are looking for a vacation rental with a fitness center, consider staying at Ginosi Chicago Apartel. This Chicago vacation rental comes with a well-equipped fitness center with treadmills and exercise bikes, among others. The gym also provides guests with a personal trainer to assist both beginners and pros.

For those who enjoy swimming, consider staying at Uptown Gem. This establishment has a great indoor heated pool where you can relax and unwind as you sip on delicious cocktails by the pool. Wicker lounge chairs are also available for guests who would like to sit and relax by the pool. The management also stations a lifeguard at the pool to ensure the safety of swimmers.

If you’re visiting Chicago and are looking for a vacation rental that provides laundry services, consider staying at Entire 2br. This Chicago house rental provides laundry services convenient for travelers with families or on business. The vacation rental also ensures that the guest’s laundry is well handled, and you shouldn’t worry about any misplacement while they’re being laundered.

Choose a vacation rental when you want to be more indipendent and you want to come and go as you please. When you are staying in a vacation rental you can cook your own meals and experience Chicago as a true local!