Search Holiday Rentals in Southwest Side

Start date: Check-in selected.
To Date
End date: Check-out
    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

Tonight
18 Sep - 19 Sep
Tomorrow
19 Sep - 20 Sep
This weekend
19 Sep - 21 Sep
Next weekend
26 Sep - 28 Sep

Top Holiday Rentals in Southwest Side

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (922)
"This area is perfect we will definitely be back."
The price is 4.013.717 ₫
5.485.890 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (520)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (355)
"Real nice place 5 stars ill be back."
Level Chicago – Old Town
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (658)
"Dangerous area at times… but not always bad. And a quick walk to the safe areas for sure!!! I would definitely stay here again."
The price is 4.194.420 ₫
4.924.091 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (202)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very good, (360)
"Great stay!"
The price is 3.401.988 ₫
3.993.591 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (221)
"Great location and lovely amenities. "
The price is 3.904.240 ₫
4.583.187 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (342)
"Fantastic property with an amazing view. Easy walk to food, shopping and the lake. Would absolutely stay again "
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.2 out of 10, Very good, (48)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is 4.462.177 ₫
5.238.150 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (167)
"This place has everything for a multi-night stay."
Kasa River North Chicago
The Gem Museum Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is 5.625.148 ₫
6.439.779 ₫ total
includes taxes & fees
24 Sept - 25 Sept
The Gem Museum Suites
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (60)
"Good "
The price is 2.231.071 ₫
2.520.665 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is 4.414.673 ₫
6.500.983 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Wrigleyville Suites
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (179)
"Great location!!!"
The price is 3.930.620 ₫
4.614.155 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (137)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is 4.572.905 ₫
5.368.134 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (61)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is 5.581.634 ₫
6.552.281 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is 1.775.110 ₫
3.819.824 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Ground Floor Studios in Chicago by 747 Lofts
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.
View all properties
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"Enjoyed a wonderful stay at Hotel Felix while we were in town for a Lady GaGa concert. Room was clean and comfortable. Staff was very friendly and helpful."
Cynthia 1-night trip
Posted 1 day ago
Hotel Felix River North/Magnificent Mile