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Holiday houses in West Side

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Popular amenities for West Side holiday rentals

Other great holiday rentals in West Side

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 33 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

NoelleRating, 5 stars3 days ago
Loved our stay in Chicago! Johanna was a WONDERFUL host!! Very helpful and very clear instructions for check in and out. When I needed to get ahold of her it was super easy to connect with her. House is adorable and very home like feeling :) would definitely recommend staying here!
Superhost

Home in Schaumburg

4.8 out of 5 average rating, 80 reviews

Spacious 5 Bedroom 1 Level Renovated Modern House

NolanRating, 5 stars3 weeks ago
Great place to stay. I would recommend to everyone.
Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 39 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars3 weeks ago
Thank you for letting us stay in your beautiful home. Everything was exactly as described! Will definitely stay again
Superhost

Apartment in Chicago

4.81 out of 5 average rating, 16 reviews

City Gem: Stylish 3BR for Urban Explorers

MaríaRating, 5 stars2 months ago
Excellent lodging and host, I would come back!
Guest favourite

Home in Lockport

5 out of 5 average rating, 19 reviews

Cozy 4 Bed Ranch w Fenced Yard *Netflix

StephanieRating, 5 stars1 week ago
Samantha’s home was a great landing spot in an easy location for us to visit with nearby family. Five adults and one toddler were very comfortable and enjoyed the space. The house is well appointed with everything we needed, and we appreciated the extra toys and high chair. The neighborhood is quiet and peaceful, while being near amenities and major highways. The listing description, Samantha’s instructions, and the posted instructions in the house made for a seamless stay.
Superhost

Condo in Chicago

4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars1 month 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.
Guest favourite

Home in Lombard

5 out of 5 average rating, 21 reviews

Spacious Home in Chicago Suburbs

JonathanRating, 5 stars2 weeks ago
Fantastic spot. Came for a local event with some friends and definitely was not disappointed. Made my first ever Airbnb experience super easy and low stress.
Guest favourite

Home in Gary

4.96 out of 5 average rating, 69 reviews

Private 5 Star 2 bedroom modern city farmhouse

AmberRating, 5 stars2 months ago
Angela was very responsive. That house is right off the highway so it’s easy to get to the sheets and linens. Everything was very clean. House was set up so cute. Made us feel right at home. The neighborhood was very quiet also. Would recommend 100% and hope to stay there again when I’m in town! 5 star!

Destinations to explore

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