Title: Holiday Rentals Southwest Side from £64: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Southwest Side Travel Guide](https://expedia.co.uk/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.co.uk/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Flights to Southwest Side](https://expedia.co.uk/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southwest-Side.d553248635976475403.Car-Hire-Guide)[Southwest Side Holidays](https://expedia.co.uk/Southwest-Side.d553248635976475403.Holidays-City-Breaks)

![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by by Midway Intl Airport

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## Check prices for these dates

In two weeks

[9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[20 Mar - 22 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southwest Side holiday rentals

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1349h899x0y1-6bfcf9ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-3830b9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-166f73c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/46e46203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information)

Brighton Park

8.6/10

Excellent

(20)

"Clean and nice. My son loved the arcade game. Would stay again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nichole S.

£170

includes taxes & fees

1 Jan - 2 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-e0042c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-24e41c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/b7fc4c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-922f1c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

Brighton Park

9.2/10

Wonderful

(7)

"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jessica H.

£216

includes taxes & fees

1 Jan - 2 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information)

![Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City Apartment, City View | Living area | 75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/7fc927d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/c94fe51a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, City View | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/6a748c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ENVITAE Hotel 4 Bedroom Luxury Apartments

[](https://www.expedia.co.uk/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

Near North Side

10/10

Exceptional

(8)

"We loved at our stay at this property. It was one of the best stays we have had on vacation."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Javeria

£458

includes taxes & fees

30 Dec - 31 Dec

[](https://www.expedia.co.uk/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/f0d78c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/89c553a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/6aab6223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103920000/103911700/103911623/w1290h1735x0y538-1e6b1087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Less is more! Pet friendly Tiny Home near Chicago! 

[](https://www.expedia.co.uk/Chicago-Hotels-Less-Is-More-Pet-Friendly-Tiny-Home-Near-Chicago.h103911623.Hotel-Information)

Burr Ridge

9.8/10

Exceptional

(35)

"The place was very clean, comfortable, and even had a few furry neighbors. Effortless check in while having all the great amenities (Wi-Fi, shower, stove, fridge, TV) was an absolute advantage. No place like it exists and highly recommend staying here."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ali J.

£158

includes taxes & fees

30 Dec - 31 Dec

[](https://www.expedia.co.uk/Chicago-Hotels-Less-Is-More-Pet-Friendly-Tiny-Home-Near-Chicago.h103911623.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/44167e80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/w1320h783x0y1-af1e2329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/27e8c783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Duplex, City View | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/bd7ffa4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago luxury home suites

[](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(4)

"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Alex

£115

includes taxes & fees

30 Dec - 31 Dec

[](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 1 Queen Bed (Studio Apartment) | Private kitchen | Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/1bf06d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

[](https://www.expedia.co.uk/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1026)

"My favorite place to stay hands-down"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michele

£125

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1309495b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/c64cc369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f72f6088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/eab5965a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gold Coast Living: Modern Studio Unit

[](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(5)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Seynabou

£126

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/c52efc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/368bd483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/664fb229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Loop Living – Bright 1BR

[](https://www.expedia.co.uk/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(5)

"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey

£128

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/fb27e879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/4c1d4299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/65e9350a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/34bf7592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek 1BR Apt w/ Laundry

[](https://www.expedia.co.uk/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1)

"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

£128

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a49da56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/93c17f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/6b9648de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun-Drenched 1BR Apartment

[](https://www.expedia.co.uk/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(2)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyler B.

£128

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/3cc0a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8c87c7e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/f642030c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/9b704ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish 1BR in West Loop

[](https://www.expedia.co.uk/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(10)

"Great host comfortable bed close to restaurants and parks"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alana C.

£128

includes taxes & fees

1 Jan - 2 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/50bbce16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/640a9e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/fd6dad17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The One: A 1BR Stay That Feels Like Home

[](https://www.expedia.co.uk/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(5)

"Very nice condo in a quiet neighborhood"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Patrick

£128

includes taxes & fees

7 Jan - 8 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/adbf623a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/fe11ac9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/96789a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/4b4ff505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Modern Luxe Apt with In-Unit Laundry

[](https://www.expedia.co.uk/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1)

"Great experience for me and my wife I would definitely come back "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ShowtimeFam1

£128

includes taxes & fees

1 Jan - 2 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Café](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/715d8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

[](https://www.expedia.co.uk/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(182)

"Awesome stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sally

[](https://www.expedia.co.uk/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/72518151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/f508dbca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/e10fadd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/d4f07da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 3

[](https://www.expedia.co.uk/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(4)

"Great stay. I'm from the area but had friends visiting from out of town. This was a great location only a quick walk to Michigan Avenue and 15 minutes from the loop. The apartment was spacious, and I appreciated having disney plus/netflix signed into the TV. The check-in and check-out was really easy with an accompanying video and easy lockbox location. Host/company was also very communicative, and let me grab something I forgot in my rental after checking out!Parking space was also clutch, just...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amarah K.

£238

includes taxes & fees

5 Jan - 6 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

![Front of property – evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/9bdb478c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/a7a120b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.co.uk/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(406)

"Great location, clean room and friendly staff!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott

£181

includes taxes & fees

4 Jan - 5 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/e4126779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/53fb8853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/61009377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/1ab3553c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Twice as Nice: Chic 2BR Stay with Style & Space

[](https://www.expedia.co.uk/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information)

Downtown Chicago

9.8/10

Exceptional

(16)

"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shederia P.

£144

includes taxes & fees

1 Jan - 2 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/1310976f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/716fc9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/c0215d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/2bfb9517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Complete 1BR Home Sum

[](https://www.expedia.co.uk/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

Downtown Chicago

£128

includes taxes & fees

1 Jan - 2 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/e4656d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/c554d00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/ec6df83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/d733d639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing Chicago Studio

[](https://www.expedia.co.uk/Chicago-Hotels-Relaxing-Chicago-Studio.h115775130.Hotel-Information)

Edgewater

10/10

Exceptional

(43)

"Had a great stay. Great location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justin

£126

includes taxes & fees

5 Jan - 6 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Relaxing-Chicago-Studio.h115775130.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/3ab1d1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/91c8477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/bfb6cea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/f4be1275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

[](https://www.expedia.co.uk/Chicago-Hotels-Artistic-Loft-Rooftop-Uptown-Montrose-Beach-GymWFH.h101619097.Hotel-Information)

Uptown

10/10

Exceptional

(48)

"Clean and quiet, perfect for nights to rest after exploring the city"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe T.

£192

includes taxes & fees

13 Jan - 14 Jan 2026

[](https://www.expedia.co.uk/Chicago-Hotels-Artistic-Loft-Rooftop-Uptown-Montrose-Beach-GymWFH.h101619097.Hotel-Information)

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](https://expedia.co.uk/Hotel-Search?startDate=2026-01-12&endDate=2026-01-13&regionId=553248635976475403&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Aparthotels

[](https://www.expedia.co.uk/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=APARTMENT)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=VILLA)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=CONDO)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=COTTAGE)

Residences

[](https://www.expedia.co.uk/Hotel-Search?destination=Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475403&latLong=41.792141%2C-87.701844&adults=2&startDate=2026-03-28&d1=2026-03-28&endDate=2026-03-31&d2=2026-03-31&lodging=RESIDENCE)

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## Top Southwest Side Hotel Reviews

![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg)

### Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"Clean room, good price and helpful staff"

[](https://expedia.co.uk/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"Not only was our room spacious and spotless, but the staff was always courteous and accommodating.Great amenities. Great varied breakfast buffet."

[](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"We had a wonderful stay at Swissotel in Chicago. The staf was friendly and the rooms were spotless. Our room had a spectacular view and the location is great. I would stay there again without thinking twice about it."

[](https://expedia.co.uk/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"Room is very nice and the service was excellent."

[](https://expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"The lobby is a beautiful place to sit at Christmas time"

[](https://expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"Staff were very friendly and helpful. I would recommend this hotel to friends. Conveniently located and walkable to area attractions."

[](https://expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Clean. Modern. Elegant. Great river view from a Vista room "

[](https://expedia.co.uk/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Clean friendly hotel "

[](https://expedia.co.uk/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"Was great experience "

[](https://expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

## Find out more about Southwest Side

**Everything you need to know about** **Southwest Side** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Southwest Side holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Southwest Side. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Southwest Side holiday rentals we have selected for you start as low as £64 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Southwest Side rentals**

At Expedia, we put the best Southwest Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwest Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

- Trending destinations on Expedia.co.uk
- All accommodation types in Southwest Side

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- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

- [Apartments in Southwest Side ](https://expedia.co.uk/Southwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation)
- [Holiday Homes in Southwest Side ](https://expedia.co.uk/Southwest-Side-Private-Holiday-Homes.d553248635976475403-aaPrivateHolidayHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Southwest Side ](https://expedia.co.uk/Southwest-Side-Condos.d553248635976475403-aaCondos.Travel-Guide-Accommodation)
- [Motels in Southwest Side ](https://expedia.co.uk/Southwest-Side-Motels.d553248635976475403-aaMotels.Travel-Guide-Accommodation)
- [Serviced Apartments in Southwest Side ](https://expedia.co.uk/Southwest-Side-Apart-Hotels.d553248635976475403-aaApartHotels.Travel-Guide-Accommodation)
- [Cottages in Southwest Side ](https://expedia.co.uk/Southwest-Side-Cottages.d553248635976475403-aaCottages.Travel-Guide-Accommodation)
- [B&B in Southwest Side ](https://expedia.co.uk/Southwest-Side-Bed-And-Breakfasts.d553248635976475403-aaBedAndBreakfasts.Travel-Guide-Accommodation)
- [Hostels in Southwest Side ](https://expedia.co.uk/Southwest-Side-Hostels.d553248635976475403-aaHostels.Travel-Guide-Accommodation)
- [Guest Houses in Southwest Side ](https://expedia.co.uk/Southwest-Side-Guest-Houses.d553248635976475403-aaGuestHouses.Travel-Guide-Accommodation)
- [Resorts in Southwest Side ](https://expedia.co.uk/Southwest-Side-Hotel-Resorts.d553248635976475403-aaHotelResorts.Travel-Guide-Accommodation)
- [Villas in Southwest Side ](https://expedia.co.uk/Southwest-Side-Villas.d553248635976475403-aaVillas.Travel-Guide-Accommodation)
- [Farmstay in Southwest Side ](https://expedia.co.uk/Southwest-Side-Agritourism.d553248635976475403-aaAgritourism.Travel-Guide-Accommodation)
- [Residences in Southwest Side ](https://expedia.co.uk/Southwest-Side-Residences.d553248635976475403-aaResidences.Travel-Guide-Accommodation)

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- [Duo Milan Porta Nuova, A Tribute Portfolio Hotel](https://expedia.co.uk/Milan-Hotels-Four-Points-By-Sheraton-Milan-Center.h789026.Hotel-Information)
- [Three Corners Fayrouz Plaza Beach Resort](https://expedia.co.uk/Marsa-Alam-Hotels-The-Three-Corners-Fayrouz-Plaza-Beach-Resort.h2266461.Hotel-Information)
- [Hotels with Connecting Rooms in Glasgow](https://expedia.co.uk/Glasgow-Hotels-Hotel-With-Connecting-Rooms.0-0-d1334-thotelwithconnectingrooms.Travel-Guide-Filter-Hotels)
- [JW Marriott Hotel Bogota](https://expedia.co.uk/Bogota-Hotels-JW-Marriott-Hotel-Bogota.h3565915.Hotel-Information)
- [Hotels in Sarasota](https://expedia.co.uk/Sarasota-Hotels.d602719.Travel-Guide-Hotels)
- [Hotels near Navy Pier](https://expedia.co.uk/Navy-Pier-Hotels.0-l6069215-0.Travel-Guide-Filter-Hotels)
- [Hotels with Hot Tubs in Preston](https://expedia.co.uk/Preston-Hotels-Hotels-With-Hot-Tubs.0-0-d5661-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Best Western Andover Hotel](https://expedia.co.uk/Andover-Hotels-Best-Western-Andover-Hotel.h459203.Hotel-Information)
- [Millennium Plaza Downtown Hotel](https://expedia.co.uk/Dubai-Hotels-Millennium-Plaza-Downtown-Hotel.h7610.Hotel-Information)
- [Hotel Colosseo & Spa](https://expedia.co.uk/Shkoder-Hotels-Hotel-Colosseo-Spa.h25032160.Hotel-Information)
- [Caravan Parks South Coast](https://expedia.co.uk/South-Coast-Caravan-Parks.d6046244-aaCaravanParks.Travel-Guide-Accommodation)
- [La Medusa Dimora di Charme](https://expedia.co.uk/Mount-Vesuvius-Pompei-Hotels-La-Medusa-Hotel-Dimora-Di-Charme.h915449.Hotel-Information)
- [Hotels near McCormick Place](https://expedia.co.uk/McCormick-Place-Hotels.0-l6069191-0.Travel-Guide-Filter-Hotels)

Flights

- [Flights from Londonderry to Leeds](https://expedia.co.uk/lp/flights/ldy/lba/londonderry-to-leeds)
- [Flights to Porto Cervo](https://expedia.co.uk/Cheap-Flights-To-Porto-Cervo.d6049076.Travel-Guide-Flights)

Cars

- [Car hire in Middlesbrough](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Middlesbrough.d6557.Car-Hire-Guide)

Activities

- [Things to do in Kyoto](https://expedia.co.uk/Things-To-Do-In-Kyoto.d6131486.Travel-Guide-Activities)
- [Things to do in Sozopol](https://expedia.co.uk/Things-To-Do-In-Sozopol.d6049019.Travel-Guide-Activities)

Packages

- [Jersey Holidays](https://expedia.co.uk/Jersey.d55539.Holidays-City-Breaks)
- [Willis Tower](https://expedia.co.uk/Willis-Tower-Downtown-Chicago.d6064069.Attraction)
- [Marsa Alam Holidays](https://expedia.co.uk/Marsa-Alam.d6035091.Holidays-City-Breaks)
- [Singapore Holidays](https://expedia.co.uk/Singapore.d161.Holidays-City-Breaks)
- [Wrigley Field](https://expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction)
- [Millennium Park](https://expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction)

General

- [Visit Karachi](https://expedia.co.uk/Karachi.dx1809)

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