South Side Adventure Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 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 easyPlan, book, and manage your trip all in one place
Top Adventure holiday packages in South Side
- Hotel Felix River North/Magnificent Mile
25 Jan - 28 JanHotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.4/10 - Very good (3,177 reviews)"I stayed for a night before transferring to the main hotel while there for chicago marathon. Room was a little small but I was okay with given the price. Just know the standard rooms can be a little tight so don't be afraid to upgrade if you have lots of luggage."Reviewed November 10, 2026Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$3,293AU$2,121found 1 day agoper traveller - Park Hyatt Chicago
25 Jan - 28 JanPark Hyatt Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,003 reviews)Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$4,430AU$2,847found 1 day agoper traveller - The Talbott, Autograph Collection
25 Jan - 28 JanThe Talbott, Autograph Collection + Flight
Downtown Chicago3 nights4.5 star property9.4/10 - Exceptional (197 reviews)Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$3,635AU$2,346found 1 day agoper traveller - Trump International Hotel & Tower Chicago
25 Jan - 28 JanTrump International Hotel & Tower Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (2,082 reviews)"Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨"Reviewed November 9, 2026Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$4,057AU$2,628found 1 day agoper traveller - Kinzie Hotel
25 Jan - 28 JanKinzie Hotel + Flight
Downtown Chicago3 nights4.0 star property9.2/10 - Wonderful (2,187 reviews)"A little dated and in need of bathroom remodeling, but clean and comfortable."Reviewed November 10, 2026Return • Melbourne (MEL) - Chicago (ORD)MEL - ORD • 2 stops ORD - MEL • 2 stopsAU$3,375AU$2,202found 1 day agoper traveller
Discover the most popular places to visit in South Side
What to do in South Side
Skydeck Chicago at Willis Tower
Top Adventure South Side Hotels
"Our stay was great! The staff answered all of my questions promptly, it was easy to find and not having to pay for parking was a nice bonus."
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago"The condo was neat and clean; they had coffee and snacks available. Parking although it is in the street was open right in front of the condo. The neighborhood was also clean and we felt safe there. We were attending a show a Mcormick, and it was always an easy drive to the convention and back. The host were responsive to messages and phone calls. I would come back to this property again."
Frequently Asked Questions
How much does a South Side holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in South Side from just AU$2,121. And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to South Side?
Book everything in the one place with our South Side holiday packages. You'll find deals on flights, hotels and more that'll keep your pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1 000 000 hotels throughout the world to pick from, you'll have the flexibility to mix and match all you want.
What are the top hotels in South Side?
When it comes to properties in Carville, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are a couple of favourites. If you're considering heading to Chatham Fields, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my South Side holiday?
While not all airlines advertise ticket prices early, it's usually possible to look up international flights on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you're purchasing tickets last minute, there's a chance you could get lucky. Sometimes the lowest prices become available a few weeks prior to departure.
What does an Expedia South Side travel package include?
Expedia has everything you need to book your South Side escape, but what your package looks like is up to you. Choose from a combination of rental cars, hotels and flights. Searching for some activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package deal to suit your needs.
What should I know before booking a South Side travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we're a one-stop shop for all of them. You'll save precious cash just for combining your bookings. Whether you're embarking on a ski trip or relaxing on a sunny beach, your perfect getaway is only clicks away.
Can I choose my airline with a South Side Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to choose from all over the world. With so many choices, finding the right carrier to bring you to South Side will be a snap.
If I'm not able to travel, can I cancel my South Side holiday package?
You can. We get that even the best-laid plans can go awry, so we're here to help if you have to make changes to your South Side holiday package. It may be possible to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.