Photo by Steve Luzzo

Holiday Homes in Far Southwest Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Featured Holiday Homes in Far Southwest Side and around

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The One: A 1BR Stay That Feels Like Home

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is €189
includes taxes & fees
1 Sept - 2 Sept
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is €350
includes taxes & fees
4 Sept - 5 Sept
Cozy house in the city

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (9)
"Very clean in a safe neighborhood. I would stay here again"
The price is €175
includes taxes & fees
2 Sept - 3 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (24)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is €125
includes taxes & fees
2 Sept - 3 Sept
Cozy studio in Andersonville Chicago

Honeycomb Hideout w/ 2 bedrooms

The price is €370
includes taxes & fees
1 Sept - 2 Sept
Honeycomb Hideout w/ 2 bedrooms

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

The price is €322
includes taxes & fees
2 Sept - 3 Sept
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is €263
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is €434
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (10)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is €398
includes taxes & fees
2 Sept - 3 Sept
Spacious 3br home near Chicago, fenced yard for pets

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (3)
"Clean, comfortable, and would definitely stay again!"
The price is €192
includes taxes & fees
1 Oct - 2 Oct
Great Layout – Spacious 2BR Apt

Cozy Studio in Portage Park

The price is €165
includes taxes & fees
1 Sept - 2 Sept
Cozy Studio in Portage Park

Peaceful 1BR Escape in Evanston

9.4 out of 10, Exceptional, (3)
"Quiet, clean and spacious! A peaceful neighborhood. "
The price is €170
includes taxes & fees
3 Sept - 4 Sept
Peaceful 1BR Escape in Evanston

Homey 1BR Space Apartment

9.2 out of 10, Wonderful, (5)
"This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night."
The price is €168
includes taxes & fees
1 Oct - 2 Oct
Homey 1BR Space Apartment

Cozy & Furnished 2BR Unit

9.8 out of 10, Exceptional, (7)
The price is €190
includes taxes & fees
1 Oct - 2 Oct
Cozy & Furnished 2BR Unit

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is €544
includes taxes & fees
2 Sept - 3 Sept
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

1BR Chic & Sunny Place

9.4 out of 10, Exceptional, (3)
"Location was perfect for visiting family and getting around the city. Bed was extra comfy and the AC worked wonderfully. Will stay here again on our next visit. "
The price is €249
includes taxes & fees
14 Sept - 15 Sept
1BR Chic & Sunny Place

Roscoe Retreat · Cozy 2BR in Chicago

The price is €231
includes taxes & fees
7 Sept - 8 Sept
Roscoe Retreat · Cozy 2BR in Chicago

Stylish 4BR South Loop Home State 23-202

10.0 out of 10, Exceptional, (1)
"Very happy with stay. Good communication from property host. "
Stylish 4BR South Loop Home State 23-202
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Far Southwest Side Hotel Reviews

Find out more about Far Southwest Side

Find out more about Far Southwest Side

Far Southwest Side Holiday Homes information

Number of reviews
Accommodation
Holiday Homes
Lowest Price
Highest Price