Title: South Side Holidays 2026 from £632 | Expedia.co.uk [South Side Travel Guide](https://expedia.co.uk/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Holiday Rentals in South Side](https://expedia.co.uk/South-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[Flights to South Side](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Holidays from £632 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ## Top South Side Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![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 £632 per person 4 Mar - 10 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on 19 Jan 2026 ![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 Save 100% on your flight £1,220 per person 15 Apr - 20 Apr found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 Jan 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 Save 100% on your flight £997 per person 4 Mar - 9 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on 24 Jan 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 £659 per person 4 Mar - 9 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Beautiful room, great location. Will definitely stay there again. Reviewed on 28 Jan 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 £765 per person 4 Mar - 9 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on 8 Jan 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.co.uk/South-Side.dx553248635074842823) ![Chicago Museum of Science and Industry](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 3/5(1 area review) Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House. [Find hotels in Hyde Park](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=117842) ![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 4/5(2 area reviews) If you're spending time in Chinatown, you might enjoy attractions like South Wentworth Street and Chinatown Gateway. You might also enjoy the neighbourhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city. [Find hotels in Chinatown](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6003647) ![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 1 out of top 10 points of interest in this area 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 Theatre on the Lake, and jump on the metro at Halsted Station (Orange Line) to get around the city. [Find hotels in Bridgeport](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6132075) ![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(4 area reviews) Consider exploring the abundant dining options in Bronzeville. If sightseeing is on the list, Lake Michigan is a top attraction. Hop on the metro at 35th-Bronzeville-IIT Station or Indiana Station to see more of the area. [Find hotels in Bronzeville](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6132245) ![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 If you're spending time in Douglas, you might enjoy attractions like Lake Michigan and McCormick Tribune Center. You might also enjoy the neighbourhood's ample dining options before hopping on the metro at 35th-Bronzeville-IIT Station to see more of the city. [Find hotels in Douglas](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6132367) ## South Side Essential Information | Language | English | | --------------- | -------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | ## Top hotels in South Side ![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 £86 2 Feb - 3 Feb includes taxes & fees 9.4/10 Exceptional! (1,011 reviews) Clean and great service Reviewed on 25 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%2F02%2F2026&selected=64624399&PinnedHotelID=64624399&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 Fully refundableReserve now, pay when you stay 8.8/10 Excellent! (1,176 reviews) Courteous staff and got a discount at the Starbucks that's on the corner. Reviewed on 22 Jan 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=13320264&PinnedHotelID=13320264&HadPinnedHotel=true®ionId=553248635074842823) [](https://expedia.co.uk/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=13320264&PinnedHotelID=13320264&HadPinnedHotel=true®ionId=553248635074842823) ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Chicago – Midway Airport S by IHG 7353 S Cicero Avenue Chicago IL Fully refundable £78 2 Feb - 3 Feb includes taxes & fees 8.2/10 Very Good! (1,001 reviews) The room was spotless and the staff was courteous good service Reviewed on 18 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%2F02%2F2026&selected=2190&PinnedHotelID=2190&HadPinnedHotel=true®ionId=553248635074842823) [See all 472 properties in South Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F01%2F2026&endDate=31%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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Popular places to visit ![Aerial View of a large University in the Chicago Neighborhood of Hyde Park](https://images.trvl-media.com/place/6064081/ed547d2b-1357-42b3-840a-f88661f7db9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Chicago Explore the campus of University of Chicago during your travels in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area. [](https://expedia.co.uk/University-Of-Chicago-Hyde-Park.d6064081.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.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) ### What to do in South Side ![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Navy Pier Centennial Wheel Ticket £18 per adult **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details) ![Chicago C3® : Save on admission to your choice of 3 top attractactions](https://mediaim.expedia.com/localexpert/46362450/da44d619-18fc-4969-97e2-f7b8d0da99b5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago C3® by CityPASS® £79 per adult **90%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.activity-details) ![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 £25 per adult **96%** of travellers recommend [](https://expedia.co.uk/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in South Side](https://expedia.co.uk/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 travellers 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 - Accommodation - Flights - Packages - Cars - [4 Star Hotels in McKinley Park ](https://www.expedia.co.uk/4Star-McKinley-Park-Chicago-Hotels.s40-n6132389-0.Travel-Guide-Filter-Hotels) - 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[Visit Grand Boulevard ](https://www.expedia.co.uk/Chicago-Grand-Boulevard.dx6132310) - [Chicago Harbor Lighthouse ](https://www.expedia.co.uk/Chicago-Harbor-Lighthouse-Chicago.d6064039.Attraction) - [Visit Hyde Park ](https://www.expedia.co.uk/Chicago-Hyde-Park.dx117842) - [Visit Jackson Park Highlands ](https://www.expedia.co.uk/Chicago-Jackson-Park-Highlands.dx6132329) - [Visit Near South Side ](https://www.expedia.co.uk/Chicago-Near-South-Side.dx6132399) - [Visit Prairie District ](https://www.expedia.co.uk/Chicago-Prairie-District.dx553248635976473159) - [Chicago Riverwalk ](https://www.expedia.co.uk/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Attraction) - [Visit South Commons ](https://www.expedia.co.uk/Chicago-South-Commons.dx6132263) - [Visit South Loop ](https://www.expedia.co.uk/Chicago-South-Loop.dx6130108) - [Chicago Theatre ](https://www.expedia.co.uk/Chicago-Theatre-Downtown-Chicago.d6064049.Attraction) - [Chicago Water Tower ](https://www.expedia.co.uk/Chicago-Water-Tower-Downtown-Chicago.d6064051.Attraction) - 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[Michigan Avenue ](https://www.expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction) - [Millennium Park ](https://www.expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction) - [Navy Pier ](https://www.expedia.co.uk/Navy-Pier-Downtown-Chicago.d6069215.Attraction) - [Robie House ](https://www.expedia.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) - [Sr Crown Hall ](https://www.expedia.co.uk/SR-Crown-Hall-Bronzeville.d553248621533116346.Attraction) - [S.s. Peter and Paul Church ](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Shops at North Bridge ](https://www.expedia.co.uk/Shops-At-North-Bridge-Downtown-Chicago.d6227764.Attraction) - [South Loop Holidays ](https://www.expedia.co.uk/South-Loop.d6130108.Holidays-City-Breaks) - [The Loop Holidays ](https://www.expedia.co.uk/The-Loop.d800024.Holidays-City-Breaks) - [United Center ](https://www.expedia.co.uk/United-Center-Near-West-Side.d6064077.Attraction) - [Willis Tower ](https://www.expedia.co.uk/Willis-Tower-Downtown-Chicago.d6064069.Attraction) - [Car hire near Chicago ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Chicago.d178248.Car-Hire-Guide) - [Car hire near Lake Meadows Park ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lake-Meadows-Park.d6132351.Car-Hire-Guide) - [Enterprise Rental Cars in Hyde Park ](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Southwest Side ](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Southwest-Side.d553248635976475403-c15.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Hyde Park ](https://www.expedia.co.uk/Europcar-Car-Rentals-In-Hyde-Park.d117842-c14.Car-Rental-Guide-Suppliers) \* Savings based on package bookings compared to the price of the same components booked separately. 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