Title: South Side Vacation Packages & Trips 2026 from CA $1,120 | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Vacation Packages ## 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 ## Top South Side Vacation Deals 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 CA $1,120 per person Jun 12 - Jun 16 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.2/10 Wonderful! (436 reviews) Was a little noisy but I think that was just my unit. Facilities were top notch! Reviewed on Apr 4, 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 $1,941 per person May 22 - May 29 found 15 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (3,688 reviews) The room was clean. Very modern hotel. Great service and staff. Great experience overall. Reviewed on Apr 7, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,578 per person Jun 1 - Jun 5 found 15 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (2,427 reviews) Great place to stay Reviewed on Apr 7, 2026 ![Cambria Hotel Chicago Loop - Theatre District](https://images.trvl-media.com/lodging/19000000/18060000/18057400/18057374/8a20be9a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cambria Hotel Chicago Loop - Theatre District Downtown Chicago CA $1,242 per person May 14 - May 18 found 10 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,551 reviews) Clean room Nice music mirror Reviewed on Apr 6, 2026 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/8920c075_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago CA $1,912 per person May 22 - May 29 found 15 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.2/10 Wonderful! (1,332 reviews) The Thompson Chicago is a wonderful boutique Hotel located in the perfect part of the city. Reviewed on Apr 6, 2026 ## Where to stay in South Side Find the best South Side areas and neighborhoods for the activities you enjoy most. [Learn more about South Side](https://expedia.ca/South-Side.dx553248635074842823) ![Hyde Park](https://images.trvl-media.com/place/6064043/29f0986c-b49b-485b-8fcc-9b5424ca802f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Hyde Park 4 out of top 10 points of interest in this area 4/5(4 area reviews) Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House. [Find hotel + flight trips in Hyde Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Hyde%20Park&DestID=117842&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![EyeEm Custom Shoots Q4 2018](https://images.trvl-media.com/place/6003647/e3f94976-3603-43a7-a36a-570792654b8d.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Chinatown 3.5/5(13 area reviews) If you're spending time in Chinatown, you might enjoy attractions like South Wentworth Street and Chinese American Museum of Chicago. You might also enjoy the neighborhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city. [Find hotel + flight trips in Chinatown](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Chinatown&DestID=6003647&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![www.alamy.com](https://images.trvl-media.com/place/6132075/cfd0936f-7a46-4712-9bcf-9fc886479e02.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bridgeport Well-liked for its restaurants and churches, Bridgeport is worth a visit. Check out the variety of things to see and do like Bridgeport Art Center and Zhou B Art Center, and jump on the metro at Halsted Station (Orange Line) to get around the city. [Find hotel + flight trips in Bridgeport](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bridgeport&DestID=6132075&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Bronzeville Bridge ](https://images.trvl-media.com/place/6132245/bdf0ca23-8e04-4a02-a6f8-aaeeeaf14c16.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bronzeville 1 out of top 10 points of interest in this area 3.5/5(14 area reviews) Travelers choose Bronzeville for its abundant dining options. Hop aboard the metro at 35th-Bronzeville-IIT Station or Indiana Station and check out top sights like Lake Michigan. [Find hotel + flight trips in Bronzeville](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bronzeville&DestID=6132245&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Aerial Chicago Douglas Neighborhood](https://images.trvl-media.com/place/6132367/ef7d8028-54cc-4a3b-8ea2-51bfd9daba05.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Douglas 1 out of top 10 points of interest in this area Visitors often come to Douglas for its abundant dining options, but many stay to explore sights like Lake Michigan and McCormick Tribune Center. Getting around the area on the metro is easy if you catch a ride at 35th-Bronzeville-IIT Station. [Find hotel + flight trips in Douglas](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Douglas&DestID=6132367&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to South Side? Choose your dates ## South Side Hotel Deals ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Chicago – Midway Airport S by IHG 7353 S Cicero Avenue Chicago IL Fully refundable CA $173 CA $217 total Apr 26 - Apr 27 includes taxes & fees 8.2/10 Very Good! (998 reviews) Breakfast was a typical hotel breakfast, was pricey for what you get. Reviewed on Apr 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=2190&PinnedHotelID=2190&HadPinnedHotel=true®ionId=553248635074842823) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jaslin Hotel 261 West Cermak Rd Chicago IL CA $148 CA $174 total Apr 12 - Apr 13 includes taxes & fees 9/10 Wonderful! (1,197 reviews) The hotel was in a prime location to allowing easy access to explore the China Town. It was also in close enough distance to the event we were there for at the McCormick place which allowed us to take a quick bus ride there. The hotel was extremely clean and well kept. The staff were friendly and ... Reviewed on Apr 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=13320264&PinnedHotelID=13320264&HadPinnedHotel=true®ionId=553248635074842823) ![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SpringHill Suites by Marriott Chicago Chinatown 2357 S WENTWORTH AVE Chicago IL Fully refundableReserve now, pay when you stay CA $186 CA $218 total Apr 16 - Apr 17 includes taxes & fees 9.6/10 Exceptional! (1,004 reviews) Flawless! Reviewed on Apr 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=64624399&PinnedHotelID=64624399&HadPinnedHotel=true®ionId=553248635074842823) [See all 474 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F04%2F2026&endDate=10%2F04%2F2026®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. ![](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) ### Discover the most popular places to visit in South Side ![Griffin Museum of Science and Industry](https://images.trvl-media.com/place/6064043/29f0986c-b49b-485b-8fcc-9b5424ca802f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Griffin Museum of Science and Industry 4.5/5(81 reviews) This large, interactive museum contains a coal mine and World War II submarine among its many attractions. [](https://expedia.ca/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction) ![Robie House](https://images.trvl-media.com/place/6064059/b14a8837-fd9c-420f-a714-d7b542dc804b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Robie House Witness the simple beauty of Frank Lloyd Wright’s designs in a Chicago house that epitomizes a popular American style of architecture. [](https://expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction) #### Obama's House Find out about the history of Chicago when you spend time at Obama's House. Amble around this vibrant area's lakeside or experience its acclaimed theater scene. [](https://expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction) ### What to do in South Side ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck CA $37 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Wendella's Lake and River Architecture Tour](https://mediaim.expedia.com/localexpert/766210/243b3b6c-3da3-47e5-b0c3-a50a9169e092.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's Lake and River Architecture Tour CA $61 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-lake-and-river-architecture-tour.a766210.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) [See all activities in South Side](https://expedia.ca/things-to-do/search?rid=553248635074842823) ## Frequently asked questions ### Can I cancel my flight booking to South Side due to COVID-19? ### What's the best way to find cheap flights to South Side that have flexible change policies? ### What are some of the general tips for travelers to South Side during the COVID-19 outbreak? > - Research if any travel restrictions apply to your origin and destination before booking your flight. Also check if there are any requirements you'll need to follow on arrival, such as undergoing health assessments. > - You're required to wear a face mask at the airport, including at screening checkpoints. Be prepared to adjust your mask for ID purposes when asked. > - Rather than handing a TSA employee your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection. > - You can take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be taken out for X-ray screening. > - To minimize handling during the screening process, place items such as your belt, phone and wallet into your carry-on rather than the bins. > - Transport all food items in a clear plastic bag and also put them in a screening bin. Keeping food separate from your carry-on makes it less likely that a TSA agent will need to open your bag for inspection. ### Which airlines fly to South Side? ### How can I find cheap tickets to South Side? ### How much is a flight to South Side? ### What are the most popular airports to fly into in South Side? ### When is the cheapest time to fly to South Side? ### How much is a plane ticket to South Side? ### Which airlines with flights to South Side employ COVID-19 cleanliness policies? > - United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Canaryville Hotels ](https://www.expedia.ca/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels) - 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