Holiday Homes in 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Holiday Homes in Southwest Side

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 AU$334
includes taxes & fees
2 Sept - 3 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 AU$334
includes taxes & fees
2 Sept - 3 Sept
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is AU$366
includes taxes & fees
22 Sept - 23 Sept
Sun-Drenched 1BR Apartment
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, (9)
"Very clean in a safe neighborhood. I would stay here again"
The price is AU$308
includes taxes & fees
2 Sept - 3 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
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 AU$616
includes taxes & fees
4 Sept - 5 Sept
Cozy house in the city
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, (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 AU$211
includes taxes & fees
2 Sept - 3 Sept
Cozy studio in Andersonville Chicago
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, (10)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is AU$702
includes taxes & fees
2 Sept - 3 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 AU$765
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

9.6 out of 10, Exceptional, (49)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is AU$501
includes taxes & fees
14 Sept - 15 Sept
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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 AU$553
includes taxes & fees
2 Sept - 3 Sept
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Great Layout – Spacious 2BR Apt
Fridge, microwave, oven, stovetop

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (3)
"Clean, comfortable, and would definitely stay again!"
The price is AU$328
includes taxes & fees
22 Sept - 23 Sept
Great Layout – Spacious 2BR Apt
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 AU$977
includes taxes & fees
3 Sept - 4 Sept
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
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 AU$463
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop

Getaway Near ORD With Great Local Amenities

8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
The price is AU$411
includes taxes & fees
30 Sept - 1 Oct
Getaway Near ORD With Great Local Amenities
Cozy Studio in Portage Park
Iron/ironing board, travel cot, WiFi, bed sheets

Cozy Studio in Portage Park

The price is AU$290
includes taxes & fees
2 Sept - 3 Sept
Cozy Studio in Portage Park
Enamored in Elmhurst
Smart TV

Enamored in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay"
The price is AU$762
includes taxes & fees
2 Sept - 3 Sept
Enamored in Elmhurst
Comfortable 2BR Chicago Apt
2 bedrooms, iron/ironing board, WiFi, bed sheets

Comfortable 2BR Chicago Apt

9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
The price is AU$328
includes taxes & fees
16 Sept - 17 Sept
Comfortable 2BR Chicago Apt
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 AU$300
includes taxes & fees
3 Sept - 4 Sept
Peaceful 1BR Escape in Evanston
Cozy & Furnished 2BR Unit
Interior

Cozy & Furnished 2BR Unit

9.8 out of 10, Exceptional, (7)
The price is AU$337
includes taxes & fees
3 Sept - 4 Sept
Cozy & Furnished 2BR Unit
Prime City Stay in a 1BR Apt
1 bedroom, iron/ironing board, travel cot, WiFi

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
The price is AU$300
includes taxes & fees
7 Sept - 8 Sept
Prime City Stay in a 1BR Apt
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
Sign in
Sign up, it's free

Top Southwest Side Hotel Reviews

Find out more about Southwest Side

Find out more about Southwest Side

Southwest Side Holiday Homes information

Number of reviews
Accommodation
 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia