Title: Far Southwest Side Beach Holidays 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 - ## 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. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago £770 per person 17 Apr - 22 Apr found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (413 reviews) Room smelled like food but overall very clean, very great service and staff both night and morning shift. Reviewed on 16 Feb 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £806 per person 17 Apr - 22 Apr found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (3,422 reviews) Great breakfast buffet! Great location to Michigan Ave. I would stay here again. Reviewed on 3 Mar 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago £835 per person 17 Apr - 22 Apr found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Had a great stay!! Kelly at the front desk was so sweet Reviewed on 22 Feb 2026 ![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 £1,233 per person 17 Apr - 22 Apr found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on 3 Mar 2026 ![Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/886bf093_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel Downtown Chicago £831 per person 17 Apr - 22 Apr found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.6/10 Exceptional! (1,067 reviews) Fantastic staff, clean rooms, great location, heat can be tricky as it's an older hotel. Wish they had better TV options as The Screen Sharing rarely works Reviewed on 2 Mar 2026 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/2026-04-03/2026-04-10/?FromAirport=DUB&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 £1,233 per person 17 Apr - 22 Apr found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on 3 Mar 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago £1,994 per person 20 Apr - 27 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on 1 Mar 2026 ![Nobu Hotel Chicago](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nobu Hotel Chicago Downtown Chicago £1,378 per person 17 Apr - 22 Apr found 1 day ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (748 reviews) Has everything and more Reviewed on 28 Feb 2026 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/2026-04-03/2026-04-10/?FromAirport=DUB&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. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £746 per person 29 Apr - 2 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,422 reviews) Great breakfast buffet! Great location to Michigan Ave. I would stay here again. Reviewed on 3 Mar 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £886 per person 29 Apr - 2 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,136 reviews) Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries. Reviewed on 1 Mar 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago £1,138 per person 29 Apr - 2 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on 1 Mar 2026 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/2026-04-03/2026-04-10/?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. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £758 per person 2 Apr - 6 Apr found 15 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (3,422 reviews) Great breakfast buffet! Great location to Michigan Ave. I would stay here again. Reviewed on 3 Mar 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago £1,126 per person 20 May - 24 May just found Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (413 reviews) Room smelled like food but overall very clean, very great service and staff both night and morning shift. Reviewed on 16 Feb 2026 ![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 £1,476 per person 20 May - 24 May just found Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on 3 Mar 2026 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/2026-04-03/2026-04-10/?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 £746\. 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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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. Scan the QR code with your device camera and download our app