
Far North Side Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
- 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 Orrington / Evanston
Downtown Evanston
Save 100% on your flight
Price was €756, price is now €452 per person
€452
per person
20 Nov - 25 Nov
found 7 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
7.6/10 Good! (1,007 reviews)
Two mornings received poor service at breakfast.
King bed in room. Could not open cabinet
Reviewed on 15 Sept 2025

Pendry Chicago
Downtown Chicago
Price was €1,013, price is now €522 per person
€522
per person
20 Nov - 27 Nov
found 18 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Excellent location, great restaurants nearby. Nice, spacious rooms.
Reviewed on 3 Oct 2025



Don't see what you're looking for?
See all available trips from Boston to Far North Side
View all tripsPrice found within the past 48 hours. Click for updated prices.



The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was €3,288, price is now €2,465 per person
€2,465
per person
28 Nov - 4 Dec
found 1 day ago
Return flight included
Belgrade (BEG) 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
Don't see what you're looking for?
See all available trips from Boston to Far North Side
View all tripsPrice found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was €1,098, price is now €711 per person
€711
per person
6 Nov - 10 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Excellent location, great restaurants nearby. Nice, spacious rooms.
Reviewed on 3 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 2 hours 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
Don't see what you're looking for?
See all available trips from Dublin to Far North Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.