
North Side Holidays
- Plan, book, travel with confidence
Better together
Save up to €185 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
Price found within the past 48 hours. Click for updated prices.

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €1,104, price is now €860 per person
€860
per person
29 Dec - 2 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on 4 Oct 2025

Pendry Chicago
Downtown Chicago
Price was €1,183, price is now €890 per person
€890
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
This hotel was very nice however they have one elevator that was working for 36 floors. We constantly had to wait for the elevator and
sometimes we waited so long that we decided to take the stairs and walk down 14 flights, we ended up doing this 3 times. This was incredibly inconvenient! When the elevator was working, it stopped on every single floor as we went down.
We were there from Wednesday to Sunday, it was very frustrating!
Reviewed on 5 Oct 2025

The Peninsula Chicago
Downtown Chicago
Price was €2,048, price is now €1,564 per person
€1,564
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Excellent hotel, my only complaint would be the Peninsula food service.
We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster.
As to the main dining room the service continues, as always, to be erratic and frequently slow. Food is sometimes served hot, sometimes not.
The room service on our checkout day was absolutely abysmal. We both ordered eggs Benedict and both orders were served not a degree above room temperature. The hollandaise sauce was so cold it had solidified.
There really is no excuse for this.
And unfortunately we did not have time to return the order as we had a plane to catch and we were running a bit behind.
For an otherwise professional hotel the food service and quality is sadly lacking. It leads one to believe that the F&B manager could be a nephew, a cousin, or some other family member need of a job.
Reviewed on 27 Sept 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

South Side
While South Side isn't home to many top sights, South Beach and South Haven Lighthouse are some notable places to visit nearby.
Top hotels in North Side

Yelton Manor Bed & Breakfast
140 North Shore Drive, South Haven, MI
Fully refundableReserve now, pay when you stay
The price is €161 per night from 29 Oct to 30 Oct
€161
29 Oct - 30 Oct
includes taxes & fees
9.2/10 Wonderful! (114 reviews)
"She was able to get an early check in and quick response thank you!"
Reviewed on 30 Sept 2025

Waters View Inn
86 North Shore Drive, South Haven, MI
The price is €183 per night from 7 Oct to 8 Oct
€183
7 Oct - 8 Oct
includes taxes & fees
8.8/10 Excellent! (100 reviews)
"We stayed in Room 14. It’s has 3 beds. Very comfortable. Four adults parents/kids stayed here and enjoyed the room. Stairs. Nicely decorated. Very clean. Air conditioner. Heater available. Staff is AMAZING! Very nice morning breakfast. Beach towels. In a fabulous location to beach or downtown. Highly ..."
Reviewed on 28 Sept 2025

Victoria Resort and Bed & Breakfast
241 Oak St, South Haven, MI
9.4/10 Exceptional! (130 reviews)
"Historical, our first BnB. Easy to find. Easy to park. Shopping and food and lake nearby. We went kayaking nearby. Ate and fantastic places. Easy to maneuver. Love the big tub and fireplace. Overall nice area and stay."
Reviewed on 14 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.