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Our top choices for Southwest Side holiday rentals

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (1 review)
"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment [if available]. "
United States
Fabian H.
The price is CHF 221
includes taxes & fees
6 Apr - 7 Apr
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,118 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is CHF 134
includes taxes & fees
5 Apr - 6 Apr
Sentral Michigan Avenue

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is CHF 182
includes taxes & fees
8 Apr - 9 Apr
West Loop Living – Bright 1BR

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is CHF 141
includes taxes & fees
12 Apr - 13 Apr
Modern Comfort: 1BR Unit w/ Laundry

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 CHF 182
includes taxes & fees
8 Apr - 9 Apr
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern 2BR Retreat Near Old Town & Lincoln Park

Modern 2BR Retreat Near Old Town & Lincoln Park
Near North Side
10.0 out of 10, Exceptional, (12 reviews)
"Great stay! "
United States
Aimee B.
Modern 2BR Retreat Near Old Town & Lincoln Park

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 CHF 171
includes taxes & fees
27 Apr - 28 Apr
Chic Studio in the Heart of the Gold Coast

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (456 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is CHF 210
includes taxes & fees
5 Apr - 6 Apr
Level Chicago – Old Town

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, (4 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 CHF 355
includes taxes & fees
14 Apr - 15 Apr
River North Rooftop With In and Out Parking 3

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is CHF 438
includes taxes & fees
22 Apr - 23 Apr
Modern West Loop Gem-City Views & Prime Location 3

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Apartment is as advertised. Nicely stocked, large, clean, comfortable, nice natural light, quiet, great location, full size appliances, easy access. "
United States
Susan G.
The price is CHF 233
includes taxes & fees
13 Apr - 14 Apr
Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.4 out of 10, Exceptional, (66 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is CHF 129
includes taxes & fees
27 Apr - 28 Apr
Cozy studio in Andersonville Chicago

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 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, (12 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is CHF 373
includes taxes & fees
26 Apr - 27 Apr
Spacious 4BR Central Apartment w/ Skyline Views

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is CHF 148
includes taxes & fees
14 Apr - 15 Apr
LIVN West Loop Chicago Queen Superior Studio

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (60 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is CHF 168
includes taxes & fees
7 Apr - 8 Apr
Chic Suite/Mins to L Train /Laundry/Free Parking

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
The price is CHF 200
includes taxes & fees
22 Apr - 23 Apr
Kasa River North Chicago

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is CHF 129
includes taxes & fees
5 Apr - 6 Apr
Uptown Studio Gem Sum

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Great host, quick communication, and wonderful place to stay in Chicago. Well thought out and made our stay enjoyable. Highly recommend, we will book it again next time we are in Chicago. "
United States
Justin P.
The price is CHF 255
includes taxes & fees
5 Apr - 6 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field

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 CHF 145
includes taxes & fees
6 Apr - 7 Apr
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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