North 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 North Side
Find the best North Side areas and neighborhoods for the activities you enjoy most. Learn more about North Side
Downtown
2 out of top 10 points of interest in this area
Downtown might not have many top sights, but Warner Vineyards and Kal Haven Trail are two attractions nearby that you can check out.
Top hotels in North Side
Luxury Home on North Beach-NEW Heated Pool & Hot Tub, Firepit, Game Room & More!
South Haven MI
9.6/10 Exceptional! (48 reviews)
The house was awesome. Nice and really close to the beach. The backyard was really nice. The pool was heated which was nice. Overall just a great place to stay.
Reviewed on 28 Sept 2025
Yelton Manor Bed & Breakfast
140 North Shore Drive South Haven MI
Fully refundableReserve now, pay when you stay
The price is €164 per night from 23 Nov to 24 Nov
€164
23 Nov - 24 Nov
includes taxes & fees
9.2/10 Wonderful! (120 reviews)
Good time enjoying the weekend here!
Reviewed on 19 Oct 2025
Beachfront Luxury Home-NEW Private Heated Pool, Lake View, Firepit, Game Room
South Haven MI
9.8/10 Exceptional! (48 reviews)
Wonderful location, just 200 ft walk to the beach. The owners were very responsive and caring. Wonderful space.
Reviewed on 24 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.