Default HTG hotel image

Far Southwest 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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Far Southwest Side holiday rentals

Indoor pool

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,237 reviews)
"Great property and location."
United States
Michael
The price is RM652
RM886 total
includes taxes & fees
23 Aug - 24 Aug
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (512 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is RM1,190
RM1,498 total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
Exterior

3. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
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 Far Southwest Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"Great Chicago hotel. I would definitely stay there again. Location was good. The mattress and pillows were comfortable. The building is clean and nice looking. The staff was helpful. I love that they provide decent complimentary coffee in the morning and also teatime was complimentary; scones and tea were served at 2pm. Only two things stood out as slightly negative. The walls are not very soundproof. I could hear a couple having an argument in one room and in another, people laughing. It didn't keep me from falling asleep and my husband didn't wake up from it so I found it minor. The other thing that was a minor inconvenience was their restaurant hours didn't work out for me. But in Chicago there's so many restaurant options. So again minor."
Ana 3-night trip
Posted 3 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop

Find out more about Far Southwest Side

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

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

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

Explore a world of travel with Expedia