South Side Holidays from AU$2,484
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AU$703 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
Plan, book, and manage your trip all in one place
Top Holiday Package Deals in South Side
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was AU$5,233, price is now AU$3,988 per person
AU$3,988
per person
13 Nov - 19 Nov
found 1 day ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
I loved the location - it was very walkable and lots of restaurants/shops nearby. The room itself was average - beds were very low and the furniture was kind of odd - mostly plywood built ins. But the one room served it's purpose and was clean. The issue was, I had reserved TWO rooms, but when I arrived I was informed they only had one room for me. Apparently they didn't accept the second room reservation... Neither the Emily nor Expedia notified me that one of my "PREPAID" rooms was not reserved. There were NO rooms available in the Hotel for Saturday, nor in the entire city of Chicago on Labor Day weekend, so we were left scrambling to find a place to accomodate the six of us (i.e friends couches, etc.). Not sure which company is ultimately to blame, but needless to say, ALWAYS double check your reservation with this place before you travel.
Reviewed on 3 Sep. 2025
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,819, price is now AU$4,453 per person
AU$4,453
per person
13 Nov - 20 Nov
found 16 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Truly enjoyed our experience at this hotel. Staff very kind and helpful. Location was perfect because of its location on the Magnificent Mile and getting to other areas of interest in Chicago. The room was very comfortable and clean. Definitely recommend this hotel!
Reviewed on 4 Sep. 2025
The Langham, Chicago
Downtown Chicago
Price was AU$6,845, price is now AU$5,249 per person
AU$5,249
per person
13 Nov - 19 Nov
found 1 day ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug. 2025
Our guide on where to stay in South Side
Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach.
Our pick of the best South Side Hotel Deals
GORGEOUS Remodeled South Beach Cottage - 2 blocks from the shore!
South Haven
Two Blocks from the beach & Kids Corner close to Riverwalk and Downtown
South Haven
Baymont by Wyndham South Haven
1555 Phoenix Rd, I-196 Exit 20, South Haven, MI
Fully refundableReserve now, pay when you stay
The price is AU$130 per night from 1 Oct to 2 Oct
AU$130
1 Oct - 2 Oct
includes taxes & fees
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
