Title: Holiday Rentals Southwest Side from £73: 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in 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 [13 Nov - 14 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-11-13&endDate=2025-11-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [14 Nov - 15 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-11-14&endDate=2025-11-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [14 Nov - 16 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [21 Nov - 23 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in 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) ![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.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) ![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 (983) "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 £128 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) ![City Studio, 1 Queen Bed, Non Smoking, Kitchen (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/47000000/46240000/46231100/46231022/1d34bb7f.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/47000000/46240000/46231100/46231022/4ebb1bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kasa Magnificent Mile Chicago Downtown Chicago 9.2/10 Wonderful (617) "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) ![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 Downtown Chicago 9.0/10 Wonderful (378) "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) ![1 bedroom, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/e3b8d058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a9095b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a5314f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/ea846735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy Market Hall Apartments West Loop Downtown Chicago 8.0/10 Very good (401) "Quite and low key spot" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shunica [](https://www.expedia.co.uk/Chicago-Hotels-Sonder-Market-Hall.h91683158.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/038aeb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/de5e0137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, premium bedding, individually decorated](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/d277fc7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, premium bedding, individually decorated](https://images.trvl-media.com/lodging/99000000/98590000/98589700/98589620/a33c4e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy The Burnham Apartments Loop Downtown Chicago 8.8/10 Excellent (253) "Great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa [](https://www.expedia.co.uk/Chicago-Hotels-Sonder-The-Burnham.h98589620.Hotel-Information) ![36-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/ccdc9112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/97fa62c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/a8e87dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/45000000/44780000/44773000/44772938/a811cd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy South Wabash Apartments South Loop Near South Side 8.6/10 Excellent (712) "Love the unit and location close to multiple restaurants and shopping." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessie [](https://www.expedia.co.uk/Chicago-Hotels-Sonder-At-South-Wabash.h44772938.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) | 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) ![Lobby](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/5aeefd88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | City view](https://images.trvl-media.com/lodging/30000000/29440000/29433500/29433443/24b549c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kasa South Loop Chicago Downtown Chicago 9.4/10 Exceptional (372) "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) ![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) ![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/97000000/96300000/96299500/96299486/79c83288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Neighborhood Hotel-Little Italy Near West Side 9.6/10 Exceptional (218) "This hotel is a 10 out of 10 for me! The hotel room was clean and the location was great. When I come back next year I’m definitely coming back here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amonee [](https://www.expedia.co.uk/Chicago-Hotels-The-Neighborhood-Hotel-Little-Italy.h96299486.Hotel-Information) ![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/112ab7b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/83373d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/de34b3e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/84000000/83700000/83695900/83695822/a5b88630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy The Opal Apartments River North Downtown Chicago 8.4/10 Very good (57) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Swastika [](https://www.expedia.co.uk/Chicago-Hotels-Sonder-The-Opal.h83695822.Hotel-Information) ![50-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/d10a452f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/e0b5e4c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/36238ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/dac97393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park Downtown Chicago 8.2/10 Very good (188) "Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander [](https://www.expedia.co.uk/Chicago-Hotels-Sonder-At-Jewelers-Row.h64871080.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) ![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) ![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 Downtown Chicago 9.4/10 Exceptional (176) "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) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.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/105000000/104320000/104315700/104315648/5dcfd7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Suites Lakeview 9.6/10 Exceptional (25) "Excellent location and very clean! Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob £131 includes taxes & fees 16 Nov - 17 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information) ![Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/acb706d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 Bedroom, Kitchen (Penthouse, Washer/Dryer) | Living area | 45-inch LED TV with cable channels](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/124718c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Double Bed, Kitchen (Washer/Dryer) | 2 bedrooms, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/fe592b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen (Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/38d26f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gem Museum Suites Downtown Evanston 9.4/10 Exceptional (95) "Great stay. The studio is small but has everything necessary." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia £144 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.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) ![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) ![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) ![Desk, laptop workspace, blackout curtains, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/7a3c031a.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 (66) "This place looked like a whole in the wall I didn’t even stay the place was so dirty and I could not receive a refund looks disgusting and not even worth a $50 stay at minimum. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bria £73 includes taxes & fees 15 Nov - 16 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information) ![Free WiFi](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/489cf83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](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/e4296478.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 £262 includes taxes & fees 16 Nov - 17 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information) ![Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/1687c774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![40-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/3e0b12b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/3e40aa77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/42000000/41970000/41963600/41963526/26c37847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy Greektown Apartments Downtown Chicago 8.6/10 Excellent (65) "I enjoyed my stay! Thanks!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan [](https://www.expedia.co.uk/Chicago-Hotels-Sonder-Greektown-Suites.h41963526.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) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792882/631182fd.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) ![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 (34) "Was very clean and comfortable simply furnished but nice close to the things we were looking for. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) zack r. £129 includes taxes & fees 2 Dec - 3 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) ![Classic Apartment | Private kitchen](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/d0a14058.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) ### Stylish Apartment near Chicago Downtown Bridgeport £296 includes taxes & fees 16 Nov - 17 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-Apartment-Near-Chicago-Downtown.h119973593.Hotel-Information) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/2c5edc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/873e46ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/ac888596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/77ca5eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio in Hyde Park-Walk to Lake & University Hyde Park 9.0/10 Wonderful (9) "Good communication and easy check-in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chen £126 includes taxes & fees 3 Dec - 4 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Studio-In-Hyde-Park-Walk-To-Lake-University.h116792603.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) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792940/743dca25.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) ![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) ### Charming 2BR in Vibrant Lakeview Lakeview 9.2/10 Wonderful (27) "Check in was a breeze, unit was very clean and comfortable. Would definitely stay in this location again. Great area, with easy access to transportation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris H. £147 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Charming-2BR-In-Vibrant-Lakeview.h116792940.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=2025-11-27&endDate=2025-11-28®ionId=553248635976475403&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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%2FSouthwest-Side-Holiday-Rentals.d553248635976475403.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Holiday-Rentals.d553248635976475403.Travel-Guide-HolidayRentals) ## Top Southwest Side Hotel Reviews ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Centrally located by the Magnificent Mile. Plenty of shopping options. Access to both train and bus public transportation. Hotel is older but kept. Staff are friendly, efficient, abd aware of comings and goings. Always greeting you ss you leave snd return. Rooms and property are clean. Rooms are spacious for a large metro city. I have stayed at this location multiple times. Will always be my first choice. " [](https://expedia.co.uk/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Everything. Loved the experience. " [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Great" [](https://expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "First I made phone call day earlier before arriving Ruth answered the phone and her customer skills was absolutely amazing from there on it was great experience . To have to pay for early check in gets me upset because if check out early hotel does not reimburse me back" [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "My stay at the Hotel Riu Plaza in downtown Chicago was absolutely incredible from start to finish! The location is perfect — right in the heart of the city, close to everything, yet quiet enough for a relaxing getaway. The highlight of my stay was the breakfast buffet. It was hands down one of the best I’ve ever had at any hotel! The variety was amazing — fresh fruit, made-to-order omelets, pastries, pancakes, and plenty of healthy options too. Everything was fresh, beautifully presented, and delicious. The staff working the breakfast area were so friendly and attentive, always making sure guests had what they needed and tables were spotless. Speaking of spotless, I have to give huge credit to the cleaning staff. They kept the rooms and common areas immaculate. My room was always perfectly cleaned and restocked, and every area of the hotel — from the lobby to the elevators — was shining. You can tell they take real pride in their work. And the rooftop view — absolutely breathtaking! Whether it was morning or night, the skyline looked stunning from up there. It’s the perfect spot to relax, take photos, or just soak in the beauty of Chicago. I would 100% stay here again and highly recommend the Riu Plaza Chicago to anyone visiting the city. Fantastic service, amazing breakfast, and unbeatable views — this hotel truly exceeded all expectations!" [](https://expedia.co.uk/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Aloft Chicago Mag Mile](//images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg) ### Aloft Chicago Mag Mile 10/10 Excellent "Great stay….. we arrived super early and the staff were gracious enough to afford us an early check in that we needed due to a long delayed overnight flight. Hotel was very well staffed and a comforting atmosphere in the lounge area- fireplace, bar, pool table. Would definitely recommend- location is fantastic! " [](https://expedia.co.uk/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Eurostars Magnificent Mile](//images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "We loved our stay!! The views in the panoramic room were amazing!! Rooms were clean. Definitely coming back!! " [](https://expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "The gent at the front desk was very friendly. The room and hotel were clean. Was the room small? Yes. Buy I don't need a ton of space. I'd stay here again." [](https://expedia.co.uk/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Great " [](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 £73 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 ### 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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