Chicago vacation rentals

Chicago vacation rentals

Search hundreds of travel sites at once for vacation home deals in Chicago

Chicago, IL
Bundle with KAYAK |

Search hundreds of travel sites at once for vacation home deals in Chicago

...and more

Good to know

Low season


High season


Average price (Weeknight)


Average price (Weekend night)

Cheapest month to stay with an average 38% drop in price.
Most expensive time to stay with an average 85% rise in price.
Average Sunday to Thursday price over the last 2 weeks.
Average Friday and Saturday price over the last 2 weeks.

When to book a vacation rental in Chicago

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding the perfect Chicago vacation rental

  • Pool, hot tub, and wifi are the most popular vacation rental property amenities in Chicago
  • Vacation rentals in Chicago are around 15% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chicago.
  • The best vacation rental properties in Chicago are 2F Chicago's Little Italy near West Loop & Downtown (10.0, 21 reviews), The Avondale Guesthouse (9.5, 107), and Wrigley Oasis! Steps from the Field! - 3BD 1BA (9.5, 33), based on ratings and reviews from real travelers.
  • Bridgeport is the neighborhood in Chicago with the most affordable vacation rental properties (11 properties with an average price of $148 per night). Ethan Golden Llc, Benedictine Bed and Breakfast, and Cozy 2 Bedroom 1 Bath. Centrally located with a Private Porch! are the most popular rental properties in Bridgeport.
  • Are you traveling to Chicago on business? Consider staying at the Wicker Park Chicago in the historical Wicker Park area. This establishment is only six blocks from both Damien and Division Blueline bus stops. It saves you from the inconvenience of getting around the city thanks to its proximity to public transportation. This vacation rental is close to great restaurants and bars where guests can dine, including Smoke Daddy BBQ – Wicker Park, Innertown Pub, Milk and Honey Café, and Seadog Sushi Bar.
  • For those looking to visit famous attractions in Chicago, consider staying at Level Chicago Old Town. This Chicago vacation rental is within minutes of several attractions such as the Chicago History Museum, Architech Gallery, and Second City Theatre.
  • If you are a pet owner looking for a pet-friendly Chicago house rental, consider staying at Beautiful Room in Chicago. This vacation rental allows furry friends on request, but charges may apply. Any damages caused by the pet are charged to your account. However, it is only minutes away from Douglas Park, where you can walk and play with your pet.
  • For those traveling to Chicago for a family vacation, consider staying at Homan Square. This family-friendly vacation rental has a family room, among other family-friendly amenities, where you and your loved ones can relax and enjoy some screen time after a hyperactive day at Garfield Park, only a short distance away. This Chicago vacation rental also offers complimentary snacks and drinks to families using the family room.
  • Golf enthusiasts looking to enjoy a round of golf during their visit to Chicago will enjoy a stay at Forrestville Ave Large Suite. Within two miles of the vacation rental is a well-maintained golf course fully equipped with golf equipment, including golf carts, clubs, and balls. Guests are also provided with complimentary drinks, which should be relaxing, especially after a whole day of golf.

FAQs when booking a vacation rental in Chicago

How much is a vacation rental in Chicago?

How much is a vacation rental in Chicago for tonight?

Which are the most popular Chicago neighborhoods to stay in?

How can I find vacation rentals near me in Chicago?

Which Chicago vacation rental offers fitness facilities?

Which Chicago vacation rental has a pool?

Which vacation rental in Chicago offers laundry services?

What are the benefits of self-catering in the Chicago vacation rentals?

Where to stay in Chicago?

Our map will help you find the perfect place to stay in Chicago by showing you the exact location of each vacation rental.