Title: South Side Beach Holidays 2026/2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Beach Holidays ## Book a Beach Hotel + Flight or Car together to unlock savings Photo by Richard Remington - ## 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 South Side Price found within the past 48 hours. Click for updated prices. ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wheeler Mansion Near South Side £553 per person 27 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (4 reviews) A unique place to stay near the convention centre. Reviewed on 23 Jun 2025 ![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/6d23e5ad_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Marquis Chicago Near South Side £838 per person 12 Feb - 17 Feb found 1 day ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) Clean room, great staff, Reviewed on 26 Nov 2025 Don't see what you're looking for? See all available trips from Charlotte to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Grant Park Hotel Downtown Chicago £572 per person 13 Jan - 17 Jan found 9 hours ago Return direct flight included London (LON) to Chicago (ORD) 8.2/10 Very Good! (2,619 reviews) room was clean, though a few light bulb issues. Staff were very kind and friendly Reviewed on 1 Dec 2025 Don't see what you're looking for? See all available trips from London to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find your perfect South Side beach holiday #### How can I book the best beach holidays in South 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 South 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 South 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 South Side beach holidays, which start from £553\. Prices and availability are subject to change. Additional terms may apply. #### When can I go on a quiet beach holiday in South Side? Enjoy out-of-season seclusion on a beach holiday to South 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 South 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 South 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 South Side beach holidays? Add a little spontaneity to your beach holiday by looking for a last-minute deal in South Side. If you have set dates, pop them into the search and see what heaven awaits in just a few days. #### Can I find South Side beach holidays which are all inclusive? A beach holiday to South 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 South 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 South Side beach holiday with Expedia? Our huge range of accommodation and flights mean you’ll find the best beach holidays in South Side on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea. ## Top Beach South Side Hotels ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Wheeler Mansion 2020 South Calumet Avenue Chicago IL - 11 min drive from University of Chicago Stay at this luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Millennium Park are located ... 9/10 Wonderful! (4 reviews) A unique place to stay near the convention centre. Reviewed on 23 Jun 2025 [](https://expedia.co.uk/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information) ![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/6d23e5ad_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott Marquis Chicago 2121 South Prairie Avenue Chicago IL - 11 min drive from University of Chicago Stay at this business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge) and 24-hour room service. Our guests praise the helpful staff in ... 9/10 Wonderful! (1,000 reviews) Clean room, great staff, Reviewed on 26 Nov 2025 [](https://expedia.co.uk/Chicago-Hotels-Marriott-Marquis-Chicago.h18178914.Hotel-Information) ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency McCormick Place Chicago 2233 S Martin Luther King Dr Chicago IL - 11 min drive from University of Chicago Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (1,036 reviews) Would visit again Reviewed on 21 Nov 2025 [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) [See all 466 properties in South Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635074842823) 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. ## 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