
Miles Holidays
Photo by Richard Remington
- 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
Top Flight + Hotel Deals in Miles
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
Top hotels in Miles

Stoney Creek Inn Galena
940 Galena Square Dr, Galena, IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,232 reviews)
"Friendly staff Nice room, pool and hot tub"
Reviewed on 4 Oct 2025

Irish Cottage Inn & Suites
9853 US-20, Galena, IL
Fully refundableReserve now, pay when you stay
The price is €141 per night from 29 Oct to 30 Oct
€141
29 Oct - 30 Oct
includes taxes & fees
9.4/10 Exceptional! (1,214 reviews)
"Hotel was great. Shuttle into town was nice option. Bed was very un comfortable the first night. They gladly moved us to a different room. Bed was much better. We’d definitely stay there again."
Reviewed on 3 Oct 2025

Chestnut Mountain Resort
8700 W Chestnut Mountain Rd, Galena, IL
8.4/10 Very Good! (1,002 reviews)
"N/a"
Reviewed on 3 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.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.