Title: South Side Luxury Holidays 2025/2026 | Expedia.co.uk ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Luxury Holidays ## Book a Luxury Hotel + Flight or Car together to unlock savings 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 flight + Luxury hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency McCormick Place Chicago Near South Side £1,111 per person 29 Dec - 1 Jan found 22 hours ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9/10 Wonderful! (1,012 reviews) Huge convention center associated hotel. Very nice clean and modern rooms. Lakeside views from the convention are amazing (watch it at Sunrise). Only con is that it's kind of isolated dining wise and from more hip or active parts of the city. taxis/rideshares making a killing over here. Reviewed on 22 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-29/2026-01-01/?FromAirport=MAN&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=84736&paandie=true&HotelClass=40&dealMarker=hEcxEAl0cQr8TKY7Kq7rzmCqjS1Z6XutzA5Dt8f8a6HPb1x96ttqmMeuyR_xMmJ7) Don't see what you're looking for? See all available trips from Manchester to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-23/2025-11-30/?FromAirport=MAN&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency McCormick Place Chicago Near South Side £1,111 per person 29 Dec - 1 Jan found 22 hours ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9/10 Wonderful! (1,012 reviews) Huge convention center associated hotel. Very nice clean and modern rooms. Lakeside views from the convention are amazing (watch it at Sunrise). Only con is that it's kind of isolated dining wise and from more hip or active parts of the city. taxis/rideshares making a killing over here. Reviewed on 22 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-29/2026-01-01/?FromAirport=MAN&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=84736&paandie=true&HotelClass=40&dealMarker=hEcxEAl0cQr8TKY7Kq7rzmCqjS1Z6XutzA5Dt8f8a6HPb1x96ttqmMeuyR_xMmJ7) Don't see what you're looking for? See all available trips from Manchester to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-23/2025-11-30/?FromAirport=MAN&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Grant Park Hotel Downtown Chicago £862 per person 27 Dec - 31 Dec found 1 day ago Return flight included London (LHR) to Chicago (ORD) 8.2/10 Very Good! (2,628 reviews) For the price NO. The best option if it is available is to stay somewhere near the end of one of the L-trains with a day pass and make your way in and around town. Everyone I ask sad the noise from the mechanical things on the roof (9th) floor rooms was horrible. On my floor the road noise and the L-train was almost load. Sub $250 it’s OK, anything higher it’s a VERY maybe stay for me. Dinning options around the area a very good. Reviewed on 14 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-27/2025-12-31/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23023&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFS7MQ2DXoMm-OAPdTZ_OepGYwGy2_vzDuV2P5wOICYo0A) 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/2025-11-23/2025-11-30/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury holidays in South Side #### What can I expect from a luxury South Side holiday? Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes. #### How can I find all-inclusive luxury holidays in South Side? Tick the all-inclusive and 5-star filters to find the crème de la crème of South Side holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end. #### Can I book a cheap luxury holiday to South Side? A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to South Side starting at £862. Prices and availability are subject to change. Additional terms may apply. #### Are there luxury spa holidays in South Side? For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal South Side spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh. #### What should I look for when booking a luxury family holiday in South Side? Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore. #### Can I book luxury last-minute holidays to South Side? You can wangle a top-notch luxury holiday in South Side for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better! #### Can I book a luxury holiday in South Side with free cancellation and/or flexible dates? If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions. #### Why should I book my luxury travel to South Side with Expedia? Nobody does luxury quite like Expedia. With so many gorgeous properties in South Side to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book. ## Top Luxury South Side Hotels ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Wheeler Mansion 2020 South Calumet Avenue, Chicago, IL - 11 min drive from University of Chicago Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Soldier Field and Grant Park are located ... 10/10 Exceptional! (3 reviews) A unique place to stay near the convention centre. Reviewed on 23 Jun 2025 [](https://expedia.co.uk/Chicago-Hotels-The-Wheeler-Mansion.h7818107.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! (2,637 reviews) It was good Reviewed on 19 Oct 2025 [](https://expedia.co.uk/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) ![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 eco-certified hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (1,015 reviews) Great location, friendly staff, clean spacious room Reviewed on 18 Oct 2025 [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) [See all 450 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. 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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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)