South Side Holidays
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Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was €1,093, price is now €721 per person
€721
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The lady in the front counter when I walked in the hotel she greeted me ask me to check in and I was surprised because I thought it was only available till 3:00 p.m. but the room was available early so I checked it early and she was helpful I wish I knew her name I don't. I would recommend Swissotel to everybody.
Reviewed on 5 Oct 2025
The Emily Hotel
Downtown Chicago
Price was €1,244, price is now €825 per person
€825
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.
Reviewed on 29 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €972, price is now €674 per person
€674
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on 26 Sept 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 Michigan Maritime Museum and North Beach.
Top hotels in South Side
GORGEOUS Remodeled South Beach Cottage - 2 blocks from the shore!
South Haven
9.8/10 Exceptional! (74 reviews)
"This home was clean and comfortable. We enjoyed walking to downtown Phoenix Street and to tke Lihht house. Very close to the beach and bluffs. We loved the sunsets. We will be back."
Reviewed on 25 Sept 2025
New build in 2021! Short Walk To Beach & Downtown, Includes Hot Tub
South Haven
10/10 Exceptional! (34 reviews)
"House was clean and close to beach and downtown. Enjoyed it very much!"
Reviewed on 11 Sept 2025
Two Blocks from the beach & Kids Corner close to Riverwalk and Downtown
South Haven
10/10 Exceptional! (91 reviews)
"Great location. The house was great for 3 couples. Neighborhood very friendly."
Reviewed on 15 Sept 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.