Title: South Side Fishing Holidays 2026/2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Fishing Holidays ## Book a Fishing 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 flight + Fishing hotel deals in South Side 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 Save 100% on your flight £189 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on 22 Nov 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 Save 100% on your flight £363 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. 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 Save 100% on your flight £262 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on 3 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 Dec 2025 ![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 Save 100% on your flight £228 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on 4 Dec 2025 Don't see what you're looking for? See all available trips from Charlotte to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Fishing holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago Save 100% on your flight £335 per person 27 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on 26 Nov 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 Dec 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago Save 100% on your flight £545 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on 29 Nov 2025 Don't see what you're looking for? See all available trips from Charlotte to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Fishing holidays in South Side Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight £262 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on 3 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 Save 100% on your flight £363 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on 26 Nov 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 Dec 2025 Don't see what you're looking for? See all available trips from Charlotte to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Fishing holidays in South Side Price found within the past 48 hours. Click for updated prices. ![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 £1,163 per person 7 Feb - 11 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 ![Chicago luxury home suites](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago luxury home suites Downtown Chicago Save 100% on your flight £1,602 per person 13 Jan - 17 Jan found 9 hours ago Return direct flight included London (LON) to Chicago (ORD) 10/10 Exceptional! (1 review) Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job. Reviewed on 26 Nov 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago £1,187 per person 13 Jan - 17 Jan found 9 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on 29 Nov 2025 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/2026-01-05/2026-01-12/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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