South Side Luxury Holidays
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Luxury hotel deals in South Side
3 Night Luxury holidays in South Side
4 Night Luxury holidays in South Side
Best Western Grant Park Hotel
Reviewed on 6 Aug 2026
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 £715. 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
- 11 min drive from University of Chicago
Best Western Grant Park Hotel
- 14 min drive from University of Chicago
"The air conditioner was leaking water and made half of the carpet wet and thus the room smelt bad as well."
Reviewed on 6 Aug 2026
Hyatt Regency McCormick Place Chicago
- 11 min drive from University of Chicago
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Ticket
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* 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.
