Title: Holiday Rentals Southwest Side from £71: 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 ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [27 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-09-27&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Sept - 29 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [10 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Southwest Side ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/073ee6bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/acd4cf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/26ad2ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carlton Inn Midway Archer Heights 6.4/10 (1018) "Thanks slept well" £104 includes taxes & fees 4 Oct - 5 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/93b80b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/e45ee1e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/dccf4817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/b8a7cbaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rainbow Motel Garfield Ridge 5.6/10 (11) "It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people " £87 includes taxes & fees 30 Sept - 1 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/84aefbd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini fridge](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/b118c2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/3da50eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/6c3662e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skylark Motel Garfield Ridge 4.6/10 (118) "Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal." £93 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/f4ddba07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Mobility Accessible (Accessible Tub) | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/eae811db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/c24526f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/b8ff5ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Chicago – Midway Airport S by IHG West Lawn 8.4/10 Very good (1000) "Great stay" [](https://www.expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.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=2025-10-11&endDate=2025-10-12®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 ![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 "Clean room, staff was friendly & helpful. Location was perfect for us" [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Room was nice and the views are amazing" [](https://expedia.co.uk/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close. " [](https://expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Lovely " [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.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 "Modern & updated, clean, great views " [](https://expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "The intercontinental made my trip to Chicago perfect! " [](https://expedia.co.uk/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "It was a pleasurable stay" [](https://expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Loved my stay at Hotel Felix. I was in the city for work. I live out in the middle of nowhere, so it's very dark and quiet at night. The street noise didn't bother me as I thought it might. Staff was super friendly and helpful, and the cafe was great! Cucumber water in the lobby was a nice touch, too. The room was spotless, but prior to check-in, I had to be let into the lobby bathroom, and it was in need of some attention. The only thing I would add is that either the walls are a bit thin or noise travels through the venting system, as I heard an entire conversation carried on by two ladies. Otherwise, I loved this boutique hotel and would highly recommend it and will definitely re-book for my next trip to Chicago in a few weeks." [](https://expedia.co.uk/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.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 "Great!" [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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 £71 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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