Title: Holiday Rentals Far Southwest Side from £63: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Far Southwest Side Travel Guide](https://expedia.co.uk/Far-Southwest-Side.dx553248635976475353)[Hotels in Far Southwest Side](https://expedia.co.uk/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Flights to Far Southwest Side](https://expedia.co.uk/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Far-Southwest-Side.d553248635976475353.Car-Hire-Guide)[Far Southwest Side Holidays](https://expedia.co.uk/Far-Southwest-Side.d553248635976475353.Holidays-City-Breaks) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Far Southwest Side - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [25 Nov - 26 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-11-25&endDate=2025-11-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [26 Nov - 27 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-11-26&endDate=2025-11-27&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Far Southwest Side ![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.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) ![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) ### Sentral Michigan Avenue Downtown Chicago 9.2/10 Wonderful (991) "Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole £113 includes taxes & fees 7 Dec - 8 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information) ![49-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/5915e3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony view](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/36558100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Living area | 49-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/0ac0f470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Living area | 49-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/4ebb1bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kasa Magnificent Mile Chicago Downtown Chicago 9.2/10 Wonderful (632) "Room was very nice, location was wonderful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas [](https://www.expedia.co.uk/Chicago-Hotels-Kasa-Chicago-River-North-Apartments.h46231022.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) ![Lobby](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/a7a120b4.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) ![Deluxe Room, 1 Single Bed, City View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Level Chicago – Old Town Downtown Chicago 9.0/10 Wonderful (388) "Property was clean, centrally located with wonderful staff. Will definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle [](https://www.expedia.co.uk/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information) ![Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/603af13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Studio, 1 King Bed, Non Smoking, Kitchen (Self Check-in with Virtual Front Desk) | City view](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/bfbcc9a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/5aeefd88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Studio, 1 King Bed, Non Smoking, Kitchen (Self Check-in with Virtual Front Desk) | In-room dining](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/7934883a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kasa South Loop Chicago Downtown Chicago 9.4/10 Exceptional (376) "An excellent place to stay in Chicago downtown." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ABDULHAFEEZ [](https://www.expedia.co.uk/Chicago-Hotels-Kasa-South-Loop-Chicago.h29433443.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/05d44ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down duvets, desk](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/f5b85335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch Smart TV with satellite channels](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/042dd182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/97000000/96300000/96299500/96299486/50c31ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Neighborhood Hotel-Little Italy Near West Side 9.6/10 Exceptional (220) "Staff was courteous. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela [](https://www.expedia.co.uk/Chicago-Hotels-The-Neighborhood-Hotel-Little-Italy.h96299486.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) ![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) ![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/860305fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kasa River North Chicago Downtown Chicago 9.4/10 Exceptional (179) "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) ![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/06060406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/2626f596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/c25a1316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Suites Lakeview 9.6/10 Exceptional (26) "Excellent location and very clean! Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob £80 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/e4296478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/4c40e70c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/e66c238f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago luxury home suites Downtown Chicago 10/10 Exceptional (1) "This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. " ![New Zealand](https://a.travel-assets.com/egds/marks/flags/nz.svg) Moha £157 includes taxes & fees 26 Nov - 27 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information) ![Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/22fe051f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/81879fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Studio | Desk, laptop workspace, blackout curtains, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/d6f1cd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/11a11fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Chicago Southland I-80 & I-294 Near Casino Harvey 3.8/10 (67) "Good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abel £63 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/9262cfe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/f361fe8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/631182fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/fe8d8a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clean & Equipped 1BR Apt Lakeview 9.2/10 Wonderful (36) "Perfect for our needs, clean, convenient and great value. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa B. £124 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Clean-Equipped-1BR-Apt.h116792882.Hotel-Information) ![Classic Apartment | Private kitchen](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/65b6e2ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment | Free WiFi](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/w2571h1446x1y1-ccdca671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment | Living area](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/2b79b031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment | Bathroom | Shower, towels](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/82b5fa12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Apartment near Chicago Downtown Bridgeport £296 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-Apartment-Near-Chicago-Downtown.h119973593.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/de39e34a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/978fa548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/9984ab06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792894/d4ca51dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeview 2BR Apartment Lakeview 9.4/10 Exceptional (26) "The apartment was as described and the customer service was amazing! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael M. £140 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Lakeview-2BR-Apartment.h116792894.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68160000/68153800/68153777/w1061h809x0y0-23606953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, books](https://images.trvl-media.com/lodging/69000000/68160000/68153800/68153777/0fc78803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68160000/68153800/68153777/f5490c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68160000/68153800/68153777/86a8f241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place Near West Side 10/10 Exceptional (268) "Lovely place! Very clean and has all of the amenities necessary for a good stay. Lots of fresh towels, a fully stocked kitchen and the location is excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela C. [](https://www.expedia.co.uk/Chicago-Hotels-3F-Vintage-Graystone-In-Little-Italy-Near-Loop-UIC-United-Ct-McCormick-Place.h68153777.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) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/9b704ea8.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) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/89a0d93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 1BR in West Loop Downtown Chicago 10/10 Exceptional (10) "We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob D. £125 includes taxes & fees 30 Nov - 1 Dec [](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/71000000/70890000/70886100/70886010/03d3c9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/w828h549x0y0-b2df28f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/a351b4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/2ff2c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LakeHouse South Shore 9.4/10 Exceptional (24) "Everything was perfect with the property and the host even came to help right away when we had one issue with the lights." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isaiah P. [](https://www.expedia.co.uk/Chicago-Hotels-LakeHouse.h70886010.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/00656023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/93a33738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/6cef91d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/5d5af9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Villa West Town 10/10 Exceptional (2) " " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tomonobu [](https://www.expedia.co.uk/Chicago-Hotels-Art-Villa.h115163763.Hotel-Information) ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/e37c62cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/26d113a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/0e0ab83d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/c434b940.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2BR in Vibrant Lakeview Lakeview 9.0/10 Wonderful (30) "Great stay. Place was spic and span on arrival and host very easy to communicate with. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lukas H O. £142 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Charming-2BR-In-Vibrant-Lakeview.h116792940.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/e173d9a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, memory-foam beds, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/b3492081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/3b41a424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63360000/63358300/63358275/2f08b052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW LUXURY PENTHOUSE CONDO West Town 10/10 Exceptional (200) "Great house with a great rooftop. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francisco [](https://www.expedia.co.uk/Chicago-Hotels-NEW-LUXURY-PENTHOUSE-CONDO.h63358275.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/e55ec92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/646b6706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/d31f0f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112530000/112528300/112528246/9c740284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Luxury Penthouse Gold Coast Best Location Downtown Chicago 10/10 Exceptional (3) "I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin F. [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Luxury-Penthouse-Massive-Rooftop-Walk-To-Beach-And-Restaurants.h112528246.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/117000000/116800000/116793200/116793104/1ab3553c.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/117000000/116800000/116793200/116793104/53fb8853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twice as Nice: Chic 2BR Stay with Style & Space Downtown Chicago 9.6/10 Exceptional (14) "Had a very nice time in Chicago!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie S. £143 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.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=2025-12-09&endDate=2025-12-10®ionId=553248635976475353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=VR_BF_PROMO_553248635976475353) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CONDO) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VILLA) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=COTTAGE) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CABIN) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FFar-Southwest-Side-Holiday-Rentals.d553248635976475353.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FFar-Southwest-Side-Holiday-Rentals.d553248635976475353.Travel-Guide-HolidayRentals) ## Top Far Southwest Side Hotel Reviews ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Friendly staff, clean rooms" [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "Everything was amazing. We we're shopping for rooms that could handle 5 people without having to book a suite and RIU had the best price. But we didn't expect the level of amenities and service. The room was more than enough to handle our family of 5, the rooftop was amazing, the lobby was gorgeous. Breakfast was super busy but SUPREMELY managed. The entire staff worked as one unit, organizing, sitting guests, cleaning up and sanitizing the tables between rotations. Food was great (Smoked Salmon, who does that at a hotel breakfast!) Anytime we're staying downtown Chicago again, we'll be booking at RIU Plaza for sure" [](https://expedia.co.uk/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "I absolutely had a great experience. I loved the cleanliness, they had a bathtub, and it was in a great area. My son loved it as well. The restaurant had amazing food and the staff was very professional… we will be back. The gym room was amazing too! They cleaned our room everyday. It was so fun and amazing. Thank you so much!" [](https://expedia.co.uk/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Awesome , spotless " [](https://expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![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 "The room was spotless. Balcony was a big plus. There was a fan in the hallway that was extremely noisy- I guess there was a spill or something. Left luggage was a bit weird- they didn’t give us a claim ticket… our bags were all there when we picked them up. " [](https://expedia.co.uk/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "Awesome room, awesome staff 10/10" [](https://expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "They gave us a free room upgrade...amazing view. Very clean room, amazing facilities, great safety practices. " [](https://expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.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 "Awesome" [](https://expedia.co.uk/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Great location. Good breakfast and cocktail hour. Clean fresh smelling rooms. " [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ## Find out more about Far Southwest Side **Everything you need to know about** **Far 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 Far 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 Far Southwest Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Far Southwest Side holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Far 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 Far 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 Far Southwest Side holiday rentals we have selected for you start as low as £63 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Far Southwest Side rentals** At Expedia, we put the best Far 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 Far 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 Far 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 Far 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 Far Southwest Side ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - 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