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Search Holiday Homes in Far Southwest Side

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Browse Select Far Southwest Side Holiday Homes

Our top choices for Far Southwest Side holiday homes

The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop

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 price is £186
includes taxes & fees
15 Sept - 16 Sept
The One: A 1BR Stay That Feels Like Home
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is £170
includes taxes & fees
4 Sept - 5 Sept
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is £165
includes taxes & fees
22 Sept - 23 Sept
Sun-Drenched 1BR Apartment
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
8.8 out of 10, Excellent, (3)
"it was nice"
The price is £301
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.
Exterior detail

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

2.0 star property
10.0 out of 10, Exceptional, (10)
"Very clean in a safe neighborhood. I would stay here again"
The price is £150
includes taxes & fees
7 Sept - 8 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Cozy studio in Andersonville Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (26)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
The price is £135
includes taxes & fees
9 Sept - 10 Sept
Cozy studio in Andersonville Chicago
Honeycomb Hideout w/ 2 bedrooms
Fridge, microwave, oven, stovetop

Honeycomb Hideout w/ 2 bedrooms

The price is £318
includes taxes & fees
7 Sept - 8 Sept
Honeycomb Hideout w/ 2 bedrooms
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Travel cot, free WiFi, bed sheets

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

10.0 out of 10, Exceptional, (1)
"The house was amazing. The beds were so comfortable. The stay was so fun. Thank you for everything!"
The price is £277
includes taxes & fees
4 Sept - 5 Sept
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Fridge, microwave, oven, stovetop

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 £236
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Spacious 3br home near Chicago, fenced yard for pets
Fridge, microwave, oven, stovetop

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (11)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is £343
includes taxes & fees
7 Sept - 8 Sept
Spacious 3br home near Chicago, fenced yard for pets
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is £377
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard
Peaceful 1BR Escape in Evanston
1 bedroom, iron/ironing board, travel cot, WiFi

Peaceful 1BR Escape in Evanston

9.4 out of 10, Exceptional, (3)
"Quiet, clean and spacious! A peaceful neighborhood. "
The price is £154
includes taxes & fees
23 Sept - 24 Sept
Peaceful 1BR Escape in Evanston
Great Layout – Spacious 2BR Apt
Fridge, microwave, oven, stovetop

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (4)
"Clean, comfortable, and would definitely stay again!"
The price is £163
includes taxes & fees
17 Sept - 18 Sept
Great Layout – Spacious 2BR Apt
Cozy & Furnished 2BR Unit
Interior

Cozy & Furnished 2BR Unit

9.8 out of 10, Exceptional, (7)
The price is £160
includes taxes & fees
4 Sept - 5 Sept
Cozy & Furnished 2BR Unit
Cozy Studio in Portage Park
Iron/ironing board, travel cot, WiFi, bed sheets

Cozy Studio in Portage Park

The price is £142
includes taxes & fees
9 Sept - 10 Sept
Cozy Studio in Portage Park
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Microwave, oven, stovetop, coffee/tea maker

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 £494
includes taxes & fees
4 Sept - 5 Sept
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Cozy 2BR Apt for a Seamless Stay
2 bedrooms, WiFi, bed sheets

Cozy 2BR Apt for a Seamless Stay

8.0 out of 10, Very good, (1)
"Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. "
The price is £180
includes taxes & fees
21 Sept - 22 Sept
Cozy 2BR Apt for a Seamless Stay
1BR Chic & Sunny Place
Fridge, microwave, oven, stovetop

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 £146
includes taxes & fees
9 Sept - 10 Sept
1BR Chic & Sunny Place
Homey 1BR Space Apartment
1 bedroom, iron/ironing board, WiFi, bed sheets

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 £146
includes taxes & fees
1 Oct - 2 Oct
Homey 1BR Space Apartment
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Private kitchen

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

10.0 out of 10, Exceptional, (1)
"Very quiet and private and cl9se to alot of things "
The price is £180
includes taxes & fees
4 Sept - 5 Sept
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
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.
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Top Far Southwest Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"I enjoyed my stay here "
Carmen 1-night trip
Posted 10 days ago
The Allegro Royal Sonesta Hotel Chicago Loop

Find out more about Far Southwest Side

Find out more about Far Southwest Side

Far Southwest Side Holiday Homes information

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