Title: South Side Adventure 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 Adventure Holidays ## Book a Adventure Hotel + Flight or Car together to unlock savings Photo by by Midway Intl Airport - ## 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 flight + Adventure hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/6d23e5ad_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Marquis Chicago Near South Side £879 per person 16 Jan - 23 Jan found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Fresh breakfast; friendly staff and overall wonderful experience! Reviewed on 2 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18178914&paandie=true&HotelClass=40&dealMarker=XW9sC_9o_LWBMtHQKLE3PNfOYU28WkjmhiId4ukJ6uRFpyCALOwjhQ8JowZqfrQ6) ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wheeler Mansion Near South Side Save 100% on your flight £1,825 per person 16 Jan - 23 Jan found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 10/10 Exceptional! (3 reviews) A unique place to stay near the convention centre. Reviewed on 23 Jun 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=7818107&paandie=true&HotelClass=40&dealMarker=Vm6NnvkS1rhqONweSSKXoFFFO_vj3NWLXh9-l-jojK3FMQBRDlVtjdsYzHZyROIz) Don't see what you're looking for? See all available trips from London to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-15/2025-12-22/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Top Adventure South Side Hotels ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency McCormick Place Chicago 2233 S Martin Luther King Dr Chicago IL - 11 min drive from University of Chicago Stay at this 4-star business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean ... 9/10 Wonderful! (1,017 reviews) Staff was very friendly Reviewed on 12 Nov 2025 [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.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! (2,617 reviews) I had an awesome stay! They allowed me to check-in early for free, because I had to rush for a conference, and were super quick in responding, when I needed something. Also, there is a Paris Baguette right next to it and they give you a 10% discount for staying at the hotel. Overall, perfect place ... Reviewed on 12 Nov 2025 [](https://expedia.co.uk/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.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! (1,170 reviews) They let us check in early, which was helpful! Reviewed on 12 Nov 2025 [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) [See all 463 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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)