South Side Holidays
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,505, price is now €1,005 per person
€1,005
per person
1 Feb - 6 Feb
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on 17 Nov 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €952, price is now €662 per person
€662
per person
1 Feb - 6 Feb
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on 28 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €937, price is now €670 per person
€670
per person
1 Feb - 6 Feb
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Everything was excellent. Will definitely stay here again. I really liked the scent of the bath/shower products and the candles in the lobby
Reviewed on 20 Nov 2025
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.
Top hotels in South Side
GORGEOUS Remodeled South Beach Cottage - 2 blocks from the shore!
South Haven MI
9.8/10 Exceptional! (76 reviews)
Beautiful home very walkable to the beach & South Haven coffee shops, restaurants and shops. Look forward to returning in the future.
Reviewed on 2 Oct 2025
$1m Luxury Beach House on South Beach, Free Golf Cart with Summer Rentals
South Haven MI
10/10 Exceptional! (36 reviews)
Perfect location in beautiful South Haven! Very spacious with a great front deck! Steps from the beach and pier. A short walk to downtown. We loved this property!
Reviewed on 27 Oct 2025
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
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.