Photo by Steve Luzzo

Search Vacation 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Homes in Far Southwest Side

Cozy Room with Rooftop Lounge & City Views in River North
Property grounds

Cozy Room with Rooftop Lounge & City Views in River North

10.0 out of 10, Exceptional, (1)
"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."
The price is ￥25,391
￥37,610 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Room with Rooftop Lounge & City Views in River North
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 ￥15,282
￥32,177 total
includes taxes & fees
Sep 2 - Sep 3
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 ￥15,282
￥32,177 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is ￥15,282
￥32,177 total
includes taxes & fees
Sep 2 - Sep 3
Sun-Drenched 1BR Apartment
2 Connecting Suites at a 4⭐️ Hotel
Banquet hall

2 Connecting Suites at a 4⭐️ Hotel

The price is ￥80,926
￥109,225 total
includes taxes & fees
Sep 1 - Sep 2
2 Connecting Suites at a 4⭐️ Hotel
2 Connecting Suites at a 5⭐️ Hotel
Exterior

2 Connecting Suites at a 5⭐️ Hotel

The price is ￥387,919
￥523,411 total
includes taxes & fees
Sep 2 - Sep 3
2 Connecting Suites at a 5⭐️ Hotel
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, (7)
"Very clean in a safe neighborhood. I would stay here again"
The price is ￥21,027
￥29,311 total
includes taxes & fees
Aug 28 - Aug 29
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 ￥26,052
￥58,523 total
includes taxes & fees
Aug 27 - Aug 28
Cozy house in the city
Honeycomb Hideout w/ 2 bedrooms
Fridge, microwave, oven, stovetop

Honeycomb Hideout w/ 2 bedrooms

The price is ￥19,176
￥61,963 total
includes taxes & fees
Aug 27 - Aug 28
Honeycomb Hideout w/ 2 bedrooms
Chic Studio in Heart of Chicago
Fridge, oven, stovetop, coffee/tea maker

Chic Studio in Heart of Chicago

10.0 out of 10, Exceptional, (1)
The price is ￥13,078
￥29,231 total
includes taxes & fees
Aug 27 - Aug 28
Chic Studio in Heart of 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 ￥33,326
￥66,777 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 3br home near Chicago, fenced yard for pets
Comfy Studio in Portage Park- Great Value!
Iron/ironing board, travel crib, WiFi

Comfy Studio in Portage Park- Great Value!

The price is ￥13,078
￥27,762 total
includes taxes & fees
Aug 27 - Aug 28
Comfy Studio in Portage Park- Great Value!
Luxury Unit with Rooftop Lounge & Spectacular City Views
Property grounds

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is ￥21,512
￥32,515 total
includes taxes & fees
Sep 2 - Sep 3
Luxury Unit with Rooftop Lounge & Spectacular City Views
Enamored in Elmhurst
Smart TV

Enamored in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay"
The price is ￥31,210
￥72,475 total
includes taxes & fees
Aug 27 - Aug 28
Enamored in Elmhurst
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 ￥18,985
￥47,819 total
includes taxes & fees
Sep 8 - Sep 9
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
Property grounds

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is ￥26,684
￥39,491 total
includes taxes & fees
Sep 2 - Sep 3
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
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 ￥12,931
￥31,263 total
includes taxes & fees
Sep 22 - Sep 23
Great Layout – Spacious 2BR Apt
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, (22)
"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 ￥11,755
￥23,570 total
includes taxes & fees
Sep 2 - Sep 3
Cozy studio in Andersonville Chicago
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
Property grounds

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is ￥30,446
￥44,452 total
includes taxes & fees
Sep 2 - Sep 3
Modern Suite with Rooftop Lounge & Views of Downtown Chicago
Chic apartment with fitness room and AC in beautiful Chicago
Exterior

Chic apartment with fitness room and AC in beautiful Chicago

7.0 out of 10, Good, (2)
"This was a nice apartment and stay forThe price. Close to train station. However would be nice to add a microwave. I had to reach out by calling the host after no response about check in information on VRBO app. Received the check in information very late the night prior to my stay. Was charged 50 for early check in but when we arrived they were stillCleaning and we had to wait about 15-20minutes outside. Overall with all the inconveniences. It ended up being good stay for the price. "
The price is ￥8,082
￥35,904 total
includes taxes & fees
Aug 27 - Aug 28
Chic apartment with fitness room and AC in beautiful 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.
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

Find out more about Far Southwest Side

Find out more about Far Southwest Side

Far Southwest Side Vacation Homes information

Number of reviews
76
Accommodation
388 Vacation Homes
Lowest Price
￥8,599
Highest Price
￥22,855

Explore a world of travel with Expedia

Explore a world of travel with Expedia