Title: Beach Vacations in Far Southeast Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/b4cf8e95-0f92-4795-af28-19f97bbf7dad.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southeast 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 Southeast 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 $618 per person Feb 12 - Feb 16 found 15 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean room Clean bathroom Friendly staff Reviewed on Jan 1, 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 CA $1,025 per person Mar 11 - Mar 14 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It was like a Ritz Carlton like experience without the Ritz Carlton price tag. Reviewed on Dec 31, 2025 ![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 CA $978 per person Mar 15 - Mar 19 found 21 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $826 per person Mar 15 - Mar 19 found 21 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Excellent service from staff. Clean rooms and great location Reviewed on Jan 2, 2026 ![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 CA $862 per person Mar 15 - Mar 19 found 21 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Everything was great! Reviewed on Dec 29, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-02/2026-02-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Far Southeast 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 CA $1,025 per person Mar 11 - Mar 14 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It was like a Ritz Carlton like experience without the Ritz Carlton price tag. Reviewed on Dec 31, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,153 per person Mar 11 - Mar 14 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good. Reviewed on Dec 29, 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,471 per person Feb 4 - Feb 8 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Super comfortable bed, and the deep bathtub alone is worth the stay! Reviewed on Dec 26, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-02/2026-02-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $732 per person Mar 11 - Mar 14 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Excellent service from staff. Clean rooms and great location Reviewed on Jan 2, 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 $780 per person Mar 11 - Mar 14 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean room Clean bathroom Friendly staff Reviewed on Jan 1, 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 CA $1,025 per person Mar 11 - Mar 14 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It was like a Ritz Carlton like experience without the Ritz Carlton price tag. Reviewed on Dec 31, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-02/2026-02-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Far Southeast 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 $618 per person Feb 12 - Feb 16 found 15 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean room Clean bathroom Friendly staff Reviewed on Jan 1, 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 CA $978 per person Mar 15 - Mar 19 found 21 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 ![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 CA $1,205 per person Feb 4 - Feb 8 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It was like a Ritz Carlton like experience without the Ritz Carlton price tag. Reviewed on Dec 31, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-02/2026-02-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Far Southeast Side #### What are some benefits when booking beach vacations in Far Southeast Side? When you travel to the beach in Far Southeast 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 Southeast 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 Southeast 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 Southeast Side? There are quite a few things you can do to get cheap beach vacations in Far Southeast Side. Prices range from CA $618, 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 Southeast Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 34\. #### Why should I book family beach vacations? When you're travelling with the family to Far Southeast 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 Southeast Side? It's easy to find a beachfront vacation accommodation in Far Southeast 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 Southeast 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 Southeast 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 Far Southeast Side ![South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/00965c86_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly Chicago IL - 10 min drive from Abbott Park Stay at this condo in Chicago. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Griffin Museum of Science and Industry and ... 10/10 Exceptional! (4 reviews) Great place to stay host was very communicative which made the stay a lot easier highly recommend Reviewed on Nov 17, 2025 [](https://expedia.ca/Chicago-Hotels-South-Shore-Chicago-Condo-1-Block-To-Lake-WiFi-AC-Elevator-420-Friendly.h117794818.Hotel-Information) ![Chic Retreat, Chic Retreat "Your Urban Getaway"](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/faeb35cc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chic Retreat, Chic Retreat "Your Urban Getaway" Chicago Illinois - 13 min walk from Abbott Park Stay at this apartment in Chicago. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Griffin Museum of Science ... 6/10 (3 reviews) Nice The host was excellent and she responded to all my questions in an excellent manner. The home was beautiful as pictured. I wouldn’t mind staying there again on my next visit! I parked my car out in front and was no problems the 3 days we were there! Reviewed on Mar 22, 2025 [](https://expedia.ca/Chicago-Hotels-Chic-Retreat.h111903171.Hotel-Information) ![Modern "Blast From The Past" A Real Retreat 3Bedroom Unit](https://images.trvl-media.com/lodging/73000000/72590000/72583800/72583730/ce1d99b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Modern "Blast From The Past" A Real Retreat 3Bedroom Unit Chicago IL - 5 min drive from Abbott Park Stay at this apartment in Chicago. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Harborside International Golf ... 9.8/10 Exceptional! (7 reviews) We were in town for a 4 day sporting tournament. The "Blast From The Past" was very clean, comfortable and nice. Reviewed on Jul 27, 2025 [](https://expedia.ca/Chicago-Hotels-Modern-Blast-From-The-Past-A-Real-Retreat-3Bedroom-Unit.h72583730.Hotel-Information) [See all 4,744 properties in Far Southeast Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635976475411) 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 Far Southeast Side ](https://expedia.ca/Cheap-Flights-To-Far-Southeast-Side.d553248635976475411.Travel-Guide-Flights)[ Far Southeast Side Hotels ](https://expedia.ca/Far-Southeast-Side-Hotels.d553248635976475411.Travel-Guide-Hotels)[ Far Southeast Side Vacation Rentals ](https://expedia.ca/Far-Southeast-Side-Vacation-Rentals.d553248635976475411.Travel-Guide-VacationRentals)[ Far Southeast Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Far-Southeast-Side.d553248635976475411.Car-Rental-Guide)[ Far Southeast Side Vacations ](https://expedia.ca/Far-Southeast-Side.d553248635976475411.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