Title: Far Southwest Side Beach Holidays 2025/2026 | Expedia.co.uk ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southwest Side Beach Holidays ## Book a Beach Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## Plan, book, travel with confidence ### Better together Save up to £335 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Packages with flights are ATOL protected ## Top flight + Beach hotel deals in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Allegro Royal Sonesta Hotel Chicago Loop Downtown Chicago £696 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (2,027 reviews) The property is Great I got married there! Reviewed on 24 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=34496&paandie=true&HotelClass=40&dealMarker=lmbFn8NwYoFI6ZONL_9MovB_j-Ssk4ynPL5hPzdDzSwDneZyeJWEy5K1PTuas4EB) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £1,226 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming. Reviewed on 24 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=sgnpoo51RmifsiWbki12hW8RwepLRZ2cH2QU3gpOodXY_TJeAjxtYXKHoiPkkYvq) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago Save 100% on your flight £1,318 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on 8 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=yRjjNYZnh3WRFp_0nVgetlA_5sKl5WpYqXwffUp5PEiNGH2cM64gRXF1JSFVuiYF) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago Save 100% on your flight £883 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead Reviewed on 22 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=sgnpoo51RmifsiWbki12hZEqad7dEO5LT-PzG3-YFQedZaR0IpqHmDKrW4iSBpDw) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago Save 100% on your flight £1,387 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great place to stay. Reviewed on 20 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=40&dealMarker=yRjjNYZnh3WRFp_0nVgetlA_5sKl5WpYqXwffUp5PEgSD9ds9tJbLsUvOomGlF0R) Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-25/2025-11-01/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £1,226 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming. Reviewed on 24 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=sgnpoo51RmifsiWbki12hW8RwepLRZ2cH2QU3gpOodXY_TJeAjxtYXKHoiPkkYvq) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago Save 100% on your flight £1,318 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on 8 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=yRjjNYZnh3WRFp_0nVgetlA_5sKl5WpYqXwffUp5PEiNGH2cM64gRXF1JSFVuiYF) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago Save 100% on your flight £1,387 per person 29 Oct - 3 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great place to stay. Reviewed on 20 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-29/2025-11-03/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=50&dealMarker=yRjjNYZnh3WRFp_0nVgetlA_5sKl5WpYqXwffUp5PEgSD9ds9tJbLsUvOomGlF0R) Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-25/2025-11-01/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £1,159 per person 30 Oct - 2 Nov found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Nice rooms and excellent service! Reviewed on 24 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-30/2025-11-02/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=NjvkpQD2hesJld3RLzxki3-X0v0lLlil_CAqx0GI4lpBXgb_2BAfCll9lnmKVVRo) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago £1,464 per person 30 Oct - 2 Nov found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on 8 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-30/2025-11-02/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=NjvkpQD2hesJld3RLzxki3-X0v0lLlil_CAqx0GI4lp7D_8LC1LImiyvvWqZqzhH) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £1,416 per person 30 Oct - 2 Nov found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming. Reviewed on 24 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-30/2025-11-02/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=NjvkpQD2hesJld3RLzxki3-X0v0lLlil_CAqx0GI4lpEzkIMPEFYqzB8fJIyzzww) Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-25/2025-11-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Allegro Royal Sonesta Hotel Chicago Loop Downtown Chicago £453 per person 8 Dec - 12 Dec found 15 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9/10 Wonderful! (2,027 reviews) The property is Great I got married there! Reviewed on 24 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-12/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=34496&paandie=true&dealMarker=RtY-MKngclZR-qvDcU1kq34xlk7ewwX6d4mOi5aCMyCg0IDaukiqhhmgloAem1Bo) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £796 per person 8 Dec - 12 Dec found 15 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming. Reviewed on 24 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-12/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=q6xwP_ozGCQSj7_NdAwnFbL_UINMbLn7yn-LPW9DCHmo_7jd3R4edR1f2XY8jtBw) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago £482 per person 8 Dec - 12 Dec found 15 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Had a great uneventful stay Reviewed on 22 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-12/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=RtY-MKngclZR-qvDcU1kq34xlk7ewwX6d4mOi5aCMyCsBIWbV-ADMAoWvH8Q5kGm) Don't see what you're looking for? See all available trips from Dublin to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-10-25/2025-11-01/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find your perfect Far Southwest Side beach holiday #### How can I book the best beach holidays in Far Southwest Side? Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your Far Southwest Side beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options. #### Can I book cheap beach holidays in Far Southwest Side? For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable Far Southwest Side beach holidays, which start from £453. Prices and availability are subject to change. Additional terms may apply. #### When can I go on a quiet beach holiday in Far Southwest Side? Enjoy out-of-season seclusion on a beach holiday to Far Southwest Side during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too. #### Why should I book family holidays in Far Southwest Side with beach access? If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties. #### How can I find a Far Southwest Side beachfront holiday? For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water. #### How can I book last-minute Far Southwest Side beach holidays? Add a little spontaneity to your beach holiday by looking for a last-minute deal in Far Southwest Side. If you have set dates, pop them into the search and see what heaven awaits in just a few days. #### Can I find Far Southwest Side beach holidays which are all inclusive? A beach holiday to Far Southwest Side is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available. #### Can I book a Far Southwest Side beach trip with free cancellation and/or flexible dates? Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details. #### Why should I book a Far Southwest Side beach holiday with Expedia? Our huge range of accommodation and flights mean you’ll find the best beach holidays in Far Southwest Side on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea. ## More holidays you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Beach Holiday Destinations > - 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[Beach Holidays in Portugal](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/147/Portugal) > - [Beach Holidays in Sardinia](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/6048528/Sardinia) > - [Beach Holidays in Scotland](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/11219/Scotland) > - [Beach Holidays in South Africa](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/165/South-Africa) > - [Beach Holidays in Spain](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/166/Spain) > - [Beach Holidays in Turkey](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/183/Turkey) > - [Beach Holidays in UK](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/190/United-Kingdom) ## More Holiday Ideas [Flights to Far Southwest Side](https://expedia.co.uk/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Hotels](https://expedia.co.uk/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Far Southwest Side Holiday Rentals](https://expedia.co.uk/Far-Southwest-Side-Holiday-Rentals.d553248635976475353.Travel-Guide-HolidayRentals)[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) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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