Title: Beach Vacations in Far Southwest Side 2026 | Expedia.ca ![](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 Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Sports Illustrated Resorts Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/bc30a848_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sports Illustrated Resorts Chicago Downtown Chicago CA $1,017 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.2/10 Wonderful! (1,407 reviews) We chose this hotel for my husband’s birthday weekend. The room was spacious clean and trendy. The bed was so comfortable. The happy hour was excellent and the game room and bar on the second floor was fabulous. The customer service was phenomenal. They surprised my husband with a goody bag for his birthday which was the icing on the cake. The hotel is currently undergoing renovations but it was still a great stay. Reviewed on Mar 3, 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 CA $1,252 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Room was cleans and everything looked great. Reviewed on Mar 6, 2026 ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago CA $1,491 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.2/10 Wonderful! (2,082 reviews) Very courteous and super helpful staff. Reviewed on Mar 2, 2026 ![Le Méridien Essex Chicago](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Le Méridien Essex Chicago Downtown Chicago CA $1,570 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 8.8/10 Excellent! (1,001 reviews) Every activity I did was no further than 10 minutes away from the hotel. Reviewed on Mar 7, 2026 ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/83e4c147_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago CA $1,275 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.2/10 Wonderful! (1,001 reviews) The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again . Reviewed on Feb 17, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&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/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,198 per person Apr 6 - Apr 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,839 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on Mar 3, 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,775 per person Apr 23 - Apr 26 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.8/10 Exceptional! (1,000 reviews) Great location (very walkable), well equipped gym, very good restaurant Reviewed on Mar 5, 2026 ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c8149674_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,244 per person Apr 10 - Apr 13 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,001 reviews) The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate Reviewed on Feb 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&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 CA $1,252 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Room was cleans and everything looked great. Reviewed on Mar 6, 2026 ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago CA $1,491 per person May 1 - May 4 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.2/10 Wonderful! (2,082 reviews) Very courteous and super helpful staff. Reviewed on Mar 2, 2026 ![Le Méridien Essex Chicago](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Le Méridien Essex Chicago Downtown Chicago CA $1,570 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 8.8/10 Excellent! (1,001 reviews) Every activity I did was no further than 10 minutes away from the hotel. Reviewed on Mar 7, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&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 CA $992 per person May 25 - May 29 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Room was cleans and everything looked great. Reviewed on Mar 6, 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 CA $993 per person May 25 - May 29 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) 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 Feb 16, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,087 per person May 25 - May 29 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Beautiful property with stunning views! Reviewed on Mar 6, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-04-07/2026-04-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Far Southwest Side #### What are some benefits when booking beach vacations in Far Southwest Side? When you travel to the beach in Far Southwest 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 Far Southwest 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 Far Southwest 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 Far Southwest Side? There are quite a few things you can do to get cheap beach vacations in Far Southwest Side. Prices range from CA $992, 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 Far Southwest Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 22\. #### Why should I book family beach vacations? When you're travelling with the family to Far Southwest 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 Far Southwest Side? It's easy to find a beachfront vacation accommodation in Far Southwest 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 Far Southwest 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 Far Southwest 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. ## 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 Far Southwest Side ](https://expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[ Far Southwest Side Hotels ](https://expedia.ca/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[ Far Southwest Side Vacation Rentals ](https://expedia.ca/Far-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)[ Far Southwest Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide)[ Far Southwest Side Vacations ](https://expedia.ca/Far-Southwest-Side.d553248635976475353.Destination-Travel-Guides) \* 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