Title: South Side Cheap Holidays 2025/2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Cheap Holidays ## Book a Cheap Hotel + Flight or Car together to unlock savings Photo by by Midway Intl Airport Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 Cheap South Side Hotels ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chinatown Hotel Chicago 214 West 22nd Place, Chicago, IL - 11 min drive from University of Chicago Stay at this hotel in Chicago. Enjoy free Wi-Fi, a 24-hour front desk and daily housekeeping. Our guests praise the property condition in their reviews. Popular ... 5.4/10 (1,001 reviews) Chinatown was a very beautiful area. Reviewed on 21 Oct 2025 [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![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 - 11 min drive from University of Chicago Stay at this 3-star hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and a 24-hour front desk. Our guests praise the helpful staff and the clean ... 8.8/10 Excellent! (1,167 reviews) Room was clean and staff were friendly with check-in and giving me extra pillows. The bed was comfortable. The hotel ia in the heart of chinatown with great restaurants, pretty conveniently walkable to McCormick center. Overall very happy with my stay here. Reviewed on 24 Oct 2025 [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Grant Park Hotel 1100 S Michigan Ave, Chicago, IL - 14 min drive from University of Chicago Stay at this hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ... 8/10 Very Good! (2,612 reviews) Location was great. We could walk to several attractions. If you are going to a bears game very easy to walk to. The bakery/coffee shop connected to it was great. The hotel is a little dated but clean and safe. The only down side was the dog park right next door. I love dogs but waking up at 5 am ... Reviewed on 24 Oct 2025 [](https://expedia.co.uk/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) [See all 447 properties in South Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package®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. ## More holidays 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 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 holiday packages](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) ![](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) ## More Holiday Ideas [Flights to South Side](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[South Side Hotels](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[South Side Holiday Rentals](https://expedia.co.uk/South-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[South Side Holidays](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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 ![QR code to download the app](data:image/png;base64,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)