West Side Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for West Side vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,071 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is P6,424
P9,261 total
includes taxes & fees
Feb 10 - Feb 11
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (423 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
The price is P11,326
P14,740 total
includes taxes & fees
Feb 10 - Feb 11
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top West Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Super helpful, knowledgeable with great communication through text as well. Everything was clean. Wish parking wasn’t so much money :(. The hotel staff went above and beyond for us. Even had a kind man offer to make me a sandwich after the restaurants were closed following a night out. Took the time to make it for my voluntarily and was so nice our entire stay. Really made me smile and was such a thoughtful way to improve my stay! "
Audrey 2-night trip
Posted 3 days ago
Crowne Plaza Chicago West Loop by IHG

Find out more about West Side

Search for holiday rentals in West Side on Expedia! You can easily find your home rentals, villas, holiday apartments in West Side using one of the methods below:

  • View our selection of featured holiday rentals in West Side
  • Use the map to find apartments and other holiday homes in the West Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in West Side while they last

Look no further and take a look at our great range of rental properties in West Side!