Title: South Side Vacation Packages & Trips 2026 from CA $860 | 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/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Vacation Packages ## 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 ## Top South Side Vacation Deals 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 $860 per person Feb 14 - Feb 21 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything is ok but no parking lot and too much fee Reviewed on Jan 6, 2026 ![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 $881 per person Feb 14 - Feb 21 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Perfect location, comfortable and clean room Reviewed on Jan 5, 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 $1,760 per person Feb 14 - Feb 21 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again! Reviewed on Jan 3, 2026 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago CA $879 per person Feb 14 - Feb 21 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Th staff was mostly helpful, Jennifer that was in charge of the pool fitness area was very helpful, she gave us information on family restaurants cheap close to the hotel to eat at the first night we were in town, she was a gem, the hotel itself needs a lot of work, the windows in the room we stayed in were very drafty and we had issues keeping the room warm, the surprise costs was a shock to us, they don’t disclose the fact that they charge the paying guests at the hotel to park in the garage, the fact that they charge guests to use the pool and the fitness areas is just crazy, the pool area and hot tubs were not anything special and most hotels do not charge guests to use the amenities, we won’t be staying with the Hilton anywhere in the USA again even if we are given free room, we just weren’t impressed, it was just a basic hotel to us, Reviewed on Jan 6, 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 $972 per person Feb 14 - Feb 21 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Everything was exceptional!!!!! Reviewed on Jan 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) ![Chicago Museum of Science and Industry](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26587-Museum-Of-Science-And-Industry.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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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 Chinatown Gateway 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) ![Default Image](https://mediaim.expedia.com/destination/1/b2e69e2dbe99ba599fd0651e33351318.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) ![Default Image](https://mediaim.expedia.com/destination/9/8c1c017cd959b9905ecf2e0485df24d8.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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### South Chicago You'll enjoy the beaches and restaurants in South Chicago. You might want to make time for a stop at Lake Michigan or Mahalia Jackson Residence. [Find hotel + flight trips in South Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=South%20Chicago&DestID=6132199&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 Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 6500 S Cicero Ave Chicago IL Fully refundableReserve now, pay when you stay CA $154 CA $181 total Jan 25 - Jan 26 includes taxes & fees 8.8/10 Excellent! (1,258 reviews) Excellent breakfast, comfy bed, BIG room, VERY VERY clean. Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=201281&PinnedHotelID=201281&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 $139 CA $163 total Jan 11 - Jan 12 includes taxes & fees 9.4/10 Exceptional! (1,006 reviews) Very nice location Reviewed on Dec 31, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=64624399&PinnedHotelID=64624399&HadPinnedHotel=true®ionId=553248635074842823) ![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 - Chicago, IL 10022 South Halsted Street Chicago IL Fully refundableReserve now, pay when you stay CA $99 CA $116 total Jan 8 - Jan 9 includes taxes & fees 7/10 Good! (218 reviews) Everything was great I really enjoyed!! Reviewed on Jan 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F01%2F2026&endDate=09%2F01%2F2026&selected=115871645&PinnedHotelID=115871645&HadPinnedHotel=true®ionId=553248635074842823) [See all 469 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F01%2F2026&endDate=09%2F01%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 ![Chicago Museum of Science and Industry](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26587-Museum-Of-Science-And-Industry.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Griffin Museum of Science and Industry 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298007-Robie-House.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) ### What to do in South Side ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $46 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting CA $49 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.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 **100%** 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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