South Side Holidays from AU$600
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Top Holiday Package Deals in South Side
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was AU$1,000, price is now AU$600 per person
AU$600
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,241 reviews)
Everyone was great. A special shout out to Tareka and Nate who worked behind the bar!
Reviewed on 16 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$2,949, price is now AU$1,659 per person
AU$1,659
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent stay.
Loved everything about this hotel. Definitely coming back.
Reviewed on 18 Dec 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was AU$1,159, price is now AU$672 per person
AU$672
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on 8 Dec 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was AU$1,413, price is now AU$827 per person
AU$827
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on 14 Dec 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was AU$1,935, price is now AU$1,172 per person
AU$1,172
per person
9 Feb - 15 Feb
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was nice. Service was good.
Reviewed on 17 Dec 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 North Beach and Michigan Maritime Museum.
Our pick of the best South Side Hotel Deals
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven MI
10/10 Exceptional! (189 reviews)
We love South Haven in October and this trip did not disappoint! The location and charm of Crimson Sun was just what we were looking for.
Reviewed on 21 Oct 2025
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 24 Dec to 25 Dec
AU$114
24 Dec - 25 Dec
includes taxes & fees
7.6/10 Good! (1,003 reviews)
Room was very clean
Reviewed on 12 Dec 2025
Old Harbor Inn
515 Williams Street South Haven MI
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 21 Dec to 22 Dec
AU$222
21 Dec - 22 Dec
includes taxes & fees
9.4/10 Exceptional! (679 reviews)
We always love staying here, great location and nice rooms, right on the harbor!
Reviewed on 30 Nov 2025
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.