Holiday rentals in Chicago

Find and book unique accommodation on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chicago holiday 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 holiday rentals in Chicago

Superhost
Home in West Lawn
4.92 out of 5 average rating, 39 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars2 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Guest favourite
Flat in West Town
4.85 out of 5 average rating, 130 reviews

Condo with private terrace, free WIFI and parking

OlesyaRating, 5 stars3 weeks ago
The place looked much better than on the pictures! It has rooftop patio, spacious, clean, with a unique interior design (vintage). It had plenty of towels, dishes, comforters, so we will definitely come back there when we are in Chicago.
Guest favourite
Flat 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
Flat in Jefferson Park
4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago
Peaceful, felt like home, very spacious and comfortable
Superhost
Apartment in East Rogers Park
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars4 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Superhost
Home in Wood Dale
5 out of 5 average rating, 4 reviews

Home in the Woods!

MaikoRating, 5 stars2 weeks ago
We had such a wonderful time at Jazmin Airbnb. The place was clean and smell great! She was very responsive and we had no issue with checking into our Airbnb. Thank you for being such a great host!
Superhost
Home in Gary
4.91 out of 5 average rating, 74 reviews

Laurna Dune

DnaiyaRating, 5 stars1 month ago
I had a great stay at this Airbnb! The place was clean, cozy, and exactly as described. Angela was super responsive and made sure I had everything I needed. The only minor issue was the water pressure and temperature in the sinks, but the shower worked perfectly, so it wasn’t a big deal. Overall, this is an amazing place to stay in Gary, Indiana, and I would definitely book again!
Top guest favourite
Home in Chicago
5 out of 5 average rating, 21 reviews

Comfy Home Away From Home

ZakiRating, 5 stars1 week ago
This home completely transformed our view of Chicago. We arrived a little nervous, but the moment we walked in, we were greeted by a space that was warm, welcoming, and absolutely stunning. Every detail was thoughtfully curated, from the sleek kitchen to the plush pillows on the sectional. The kitchen is modern and fully stocked, perfect for cooking and gathering. The living room is beautifully styled and cozy, and the bedrooms felt like luxurious retreats with spa-like linens and calming decor. The basement lounge was a standout with its oversized sectional and elegant bar area, so perfect for relaxing after a long day. We especially loved the little reading nook with the blue chairs. Every corner of this home radiates peace and intentionality. It truly felt like a sanctuary. We left feeling inspired, rested, and already planning our return.

Quick stats about holiday 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