Vacation rentals in Chicago

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Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

O'Hare International Airport122 locals recommend
Wrigley Field1,004 locals recommend
Boystown92 locals recommend
Logan Square174 locals recommend
United Center200 locals recommend
Millennium Park1,243 locals recommend

Other great vacation rentals in Chicago

Top guest favourite
Home in Schaumburg
5 out of 5 average rating, 50 reviews

Great location-King beds-Kids playroom

AdamRating, 5 stars2 weeks ago
Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.
Top guest favourite
Home in Avondale
5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

MichaelRating, 5 stars1 week ago
Beth’s home was perfect for our group trip, which centered around cooking together for a Passover Seder! The kitchen had great appliances and equipment, with the space for many of us to cook at once. The house had everything we needed and we were all comfortable.
Superhost
Guest suite in Lincoln Park
4.75 out of 5 average rating, 8 reviews

The Hidden Beach House

GaryRating, 5 stars1 month ago
I enjoyed my stay here. The accommodations were basic, but the place was very clean and quiet, I found the bed very comfortable, and the location was ideal for 1 to 2 people to base out of while enjoying Old Town. The Brown Line train is just a couple of blocks from the house, which made getting to the Loop very convenient. Caid was very easy to reach with any questions. I would stay here again. One recommendation: if you drive here and need a parking pass, make those arrangements well in advance of your arrival, because they can’t be provided at a moment’s notice. I waited until the day before to ask for one and could not get it, so I had to pay $90 to park in a garage.
Guest favourite
Home in Chicago
5 out of 5 average rating, 5 reviews

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

ArissRating, 5 stars1 week ago
Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future
Guest favourite
Apartment in Albany Park
4.86 out of 5 average rating, 42 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost
Apartment in Jefferson Park
4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars3 weeks ago
Peaceful, felt like home, very spacious and comfortable
Top guest favourite
Home in Lombard
5 out of 5 average rating, 25 reviews

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars1 week ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Superhost
Home in Austin
4.85 out of 5 average rating, 68 reviews

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars1 week ago
The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

Quick stats about vacation rentals in Chicago

  • Total rentals

    11K properties

  • Total number of reviews

    542K reviews

  • Family-friendly rentals

    5.2K properties are a good fit for families

  • Pet-friendly rentals

    3.6K properties allow pets

  • Rentals with a pool

    1.2K properties have a pool

  • Rentals with dedicated workspaces

    6.9K properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago