Chicago holiday rentals

Chicago holiday rentals

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

Chicago, IL, United States
Compare vs KAYAK |

Good to know

Low season

January Cheapest month to stay with an average 60% drop in price.

High season

October Most expensive time to stay with an average 25% rise in price.

Average price (Weeknight)

£193 Average Sunday to Thursday price over the last 2 weeks.

Average price (Weekend night)

£186 Average Friday and Saturday price over the last 2 weeks.

Top tips for finding the perfect Chicago holiday rental

  • Hot tub, spa, and no minors are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 23% cheaper than hotels on average. Search here to compare prices for all accommodation types in Chicago.
  • The best holiday rental properties in Chicago are Charming One Bed in the heart of Lincoln Park (9.9, 20 reviews), Sonder - Six Points - Stunning 2br (9.9, 20), and Logan Square: Chic, Comfy 1st Floor 2 Bdrm Apt! Parking Incld! (9.8, 28), based on ratings and reviews from real travellers.
  • North Park is the neighbourhood in Chicago with the most affordable holiday rental properties (1 properties with an average price of £51 per night). Light and Bright Vintage 2 Bedroom is the most popular rental property in North Park.

FAQs when booking a holiday rental in Chicago

How much is a holiday rental in Chicago?

How much is a holiday rental in Chicago for tonight?

Which are the most popular neighbourhoods to stay in Chicago?

How can I find holiday rentals near me in Chicago?

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 holiday rental.

Best Chicago holiday rentals near Magnificent Mile

Show all