Title: Beach Vacations in South Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Beach Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Richard Remington - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Plan, book, and manage your trip all in one place ## Flight and Beach hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency McCormick Place Chicago Near South Side CA $763 per person Feb 15 - Feb 17 found 21 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,018 reviews) Room was spotless. Refrigerator noise little too much, constant and loud. Shower water too little and pressured. Market place was too pricey, but I guess that’s the usual these days in hotel market. They also have unannounced $20/day destination fee Reviewed on Dec 7, 2025 ![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 CA $1,371 per person Feb 15 - Feb 17 found 21 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (4 reviews) A unique place to stay near the convention centre. Reviewed on Jun 23, 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 CA $917 per person Feb 9 - Feb 13 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) Room was clean great easy check in Reviewed on Dec 15, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&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. ![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 CA $917 per person Feb 9 - Feb 13 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) Room was clean great easy check in Reviewed on Dec 15, 2025 ![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 CA $1,277 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Regina (YQR) to Chicago (ORD) 8.2/10 Very Good! (2,619 reviews) bad facilities. AC is very old. Noisy and it doesn’t control room temperature very well. The price was low and it is compensated by the good location Reviewed on Dec 18, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in South Side #### What are some benefits when booking beach vacations in South Side? When you travel to the beach in South Side, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. #### How can I book the best beach vacations in South Side? To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your South Side trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. #### Can I book cheap beach vacations in South Side? There are quite a few things you can do to get cheap beach vacations in South Side. Prices range from CA $763, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. #### Can I book beach packages? Yes, and you'll find quite a few beach packages available in South Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 2\. #### Why should I book family beach vacations? When you're travelling with the family to South Side, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. #### How can I find a beachfront vacation in South Side? It's easy to find a beachfront vacation accommodation in South Side using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline. #### How can I book last-minute beach vacations? Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and South Side as your destination and see what's available. #### Can I find all-inclusive beach vacations ? Yes, all you have to do to find all-inclusive beach vacations in South Side is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. #### Can I book a beach trip that's fully refundable? Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Chicago. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too. #### Why should I book beach vacations with Expedia? When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips. ## Beach Hotels in South Side ![Chicago Lake Shore Hotel](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/9cce10bf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chicago Lake Shore Hotel 4900B S Lake Shore Dr, Chicago, IL, Chicago IL - 24 min walk from University of Chicago Stay at this hotel in Chicago. Enjoy free parking and an indoor pool. Popular attractions Soldier Field and Millennium Park are located nearby. Clean room but in need of renovation Reviewed on May 22, 2023 [](https://expedia.ca/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h69827000.Hotel-Information) ![Chicago Lake Shore Hotel](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/f4afbe6d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chicago Lake Shore Hotel 4900 S Lake Shore Dr Chicago IL - 25 min walk from University of Chicago Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ... hotel was about what we expected. Nice breakfast and staff was kind Reviewed on Nov 8, 2023 [](https://expedia.ca/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h7341.Hotel-Information) ![Designer Retreat 2BR w Cowboy Pool, Fire Pit & Fast Access](https://images.trvl-media.com/lodging/123000000/122870000/122869200/122869196/88d736e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Designer Retreat 2BR w Cowboy Pool, Fire Pit & Fast Access Chicago IL - 11 min drive from University of Chicago Stay at this apartment in Chicago. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Soldier Field and Grant Park are located nearby. [](https://expedia.ca/Chicago-Hotels-Designer-Retreat-2BR-W-Cowboy-Pool.h122869196.Hotel-Information) [See all 472 properties in South Side](https://expedia.ca/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 vacations 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 Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Beach Vacation Destinations > - [Myrtle beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach) > - [Miami beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach) > - [Florida beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida) > - [Barbados beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados) > - [South beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach) > - [Palm beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach) > - [Daytona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach) > - [Newport beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach) > - [Vero beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach) > - [India beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India) > - [Laguna beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach) > - [Ontario beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario) > - [Canada beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada) > - [Barcelona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona) > - [Fort Myers beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach) > - [Portugal beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal) > - [Italy beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy) > - [Thailand beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand) > - [France beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France) ## More Vacations Ideas [Flights to South Side ](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[ South Side Hotels ](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[ South Side Vacation Rentals ](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[ South Side Car Rentals ](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[ South Side Vacations ](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)[ Things to do in South Side ](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on 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