Southwest Side Vacation Rentals

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Our top choices for Southwest Side vacation rentals

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is ¥10,607
¥40,252 total
includes taxes & fees
Apr 21 - Apr 22
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Clean and nice. My son loved the arcade game. Would stay again "
United States
Nichole S.
The price is ¥9,403
¥33,742 total
includes taxes & fees
Apr 27 - Apr 28
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,129 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is ¥22,592
¥31,198 total
includes taxes & fees
Apr 16 - Apr 17
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (464 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is ¥32,530
¥42,118 total
includes taxes & fees
Apr 22 - Apr 23
Level Chicago – Old Town

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ¥18,009
¥36,185 total
includes taxes & fees
Apr 16 - Apr 17
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (18 reviews)
"Great place"
United States
Daniel L.
The price is ¥33,308
¥101,697 total
includes taxes & fees
Apr 19 - Apr 20
Modern West Loop Gem-City Views & Prime Location 6

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (190 reviews)
"Great place! Would definitely stay again!"
United States
Katherine
The price is ¥24,225
¥43,397 total
includes taxes & fees
Apr 30 - May 1
Kasa River North Chicago

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is ¥15,618
¥33,385 total
includes taxes & fees
Apr 16 - Apr 17
West Loop Living – Bright 1BR

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is ¥11,475
¥28,531 total
includes taxes & fees
Apr 19 - Apr 20
Modern Comfort: 1BR Unit w/ Laundry

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is ¥25,499
¥72,977 total
includes taxes & fees
Apr 15 - Apr 16
River North Rooftop With In and Out Parking 3

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ¥17,053
¥34,063 total
includes taxes & fees
Apr 28 - Apr 29
Chic Studio in the Heart of the Gold Coast

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
The price is ¥43,667
¥58,737 total
includes taxes & fees
Apr 15 - Apr 16
LIVN Millennium Park Downtown Chicago 2BR

Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
The price is ¥24,209
¥74,096 total
includes taxes & fees
May 13 - May 14
Envitae Hotel, 4BR Modern Sleek Apartment

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
The price is ¥29,165
¥38,174 total
includes taxes & fees
Apr 26 - Apr 27
LIVN West Loop Chicago King Studio

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is ¥27,252
¥74,942 total
includes taxes & fees
Apr 28 - Apr 29
Downtown Chicago Stay with Free In & Out Parking 4

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (34 reviews)
"Great location and space ! Will use again "
United States
Vanessa
The price is ¥17,212
¥20,203 total
includes taxes & fees
Apr 15 - Apr 16
Wrigleyville Suites

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ¥25,689
¥47,105 total
includes taxes & fees
Apr 15 - Apr 16
The Oak Park Loft

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (14 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ¥22,790
¥71,978 total
includes taxes & fees
Apr 26 - Apr 27
Spacious 4BR Central Apartment w/ Skyline Views

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

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ¥19,937
¥28,578 total
includes taxes & fees
Apr 15 - Apr 16
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is ¥14,630
¥60,141 total
includes taxes & fees
Apr 15 - Apr 16
Premium Urban 4BR - Perfect Mix of Comfort & Location
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 Southwest Side Hotel Reviews

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