Holiday rentals in Chicago

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Popular amenities for Chicago holiday rentals

Stay near Chicago's top sights

O'Hare International Airport13 locals recommend
Wrigley Field152 locals recommend
Boystown18 locals recommend
Logan Square43 locals recommend
United Center48 locals recommend
Millennium Park207 locals recommend

Other great holiday rentals in Chicago

Superhost
Home in West Lawn
4.93 out of 5 average rating, 40 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 💗💗
Superhost
Apartment in The Loop
4.75 out of 5 average rating, 48 reviews

2BD Central Downtown Location! Spacious & Cozy

PeggyRating, 5 stars2 weeks ago
We really enjoyed our visit to Chicago. The apartment was very close to everything. we did a lot of walking and the bus lines were very convenient. Don't let the Google reviews cause you not to stay here. You get used to the train noise within hours and you kind of miss it when you leave. There were no homeless people hanging around downstairs. As a matter of fact, I only seen a few the entire time I was there. It is a very nice place to stay and I would definitely recommend it for your next visit.
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
Home in Logan Square
4.84 out of 5 average rating, 100 reviews

California Cottage/4br prime location Logan Square

JeniRating, 5 stars2 weeks ago
Daniel’s house was perfect for what we needed. Seven adult women were comfortable and enjoyed the open table space. Bathrooms in basement and main level were clean, and plenty of linens and towels were supplied for the three nights we were there. Nice location for easy pickups and stores with delivery nearby for quick groceries. Also check out Diversey House nearby - great food and drinks! Thanks for a great weekend getaway!
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.
Top guest favourite
Home in Lombard
5 out of 5 average rating, 25 reviews

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars2 weeks ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Top guest favourite
Home in Chicago
5 out of 5 average rating, 21 reviews

Comfy Home Away From Home

ZakiRating, 5 stars2 weeks 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