Title: South Side Holidays 2026 from £578 | 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/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Holidays from £578 ## Book a Hotel + Flight or Car together to unlock savings Photo by Richard Remington - ## 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. ![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 £578 per person 29 Jan - 3 Feb found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on 8 Dec 2025 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £662 per person 29 Jan - 3 Feb found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Everything was absolutely perfect Reviewed on 11 Dec 2025 ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago £590 per person 29 Jan - 3 Feb found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on 26 Nov 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 £672 per person 29 Jan - 3 Feb found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7\. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience. Reviewed on 9 Dec 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 £1,043 per person 4 Mar - 8 Mar found 24 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted. Reviewed on 11 Dec 2025 ## 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://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 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) ![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 4/5(2 area reviews) If you're spending time in Chinatown, you might enjoy attractions like Chinese American Museum of Chicago and On Leong Building. 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) ![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 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) ![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(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) ![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 hotels in South Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6132199) ## South Side Essential Information | Language | English | | --------------- | -------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | ## Top hotels in South Side ![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 £98 21 Dec - 22 Dec includes taxes & fees 8.8/10 Excellent! (1,229 reviews) The staff were helpful in explaining the free shuttle to Midway airport.The shuttle picks you up at a point outside the third level. There is a sign indicating the correct spot. You have to tell the staff when you want to get taken back to Midway and they tell you what time to come to the lobby Reviewed on 9 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&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 £98 1 Jan - 2 Jan 2026 includes taxes & fees 9.4/10 Exceptional! (1,008 reviews) From the moment we checked in, this was one of my best hotel experiences ever. I'm a Chicago native leaving abroad, and my partner and I would definitely stay here again. Love the neighborhood and this hotel is a great addition. Reviewed on 9 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%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 £63 28 Dec - 29 Dec includes taxes & fees 6.8/10 (201 reviews) Great stay Reviewed on 4 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&selected=115871645&PinnedHotelID=115871645&HadPinnedHotel=true®ionId=553248635074842823) [See all 471 properties in South Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®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 ![Robie House](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298009-Robie-House.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Chicago 4/5(15 reviews) 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://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.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) ### What to do in South Side ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour £30 per adult **94%** of travellers recommend [](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![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 **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.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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