
Greenwood Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Greenwood
Price found within the past 48 hours. Click for updated prices.


Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €906, price is now €617 per person
€617
per person
1 Feb - 6 Feb
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on 26 Nov 2025

Chicago luxury home suites
Downtown Chicago
Price was €2,929, price is now €2,019 per person
€2,019
per person
1 Feb - 6 Feb
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on 26 Nov 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,714, price is now €1,215 per person
€1,215
per person
1 Feb - 6 Feb
found 5 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Mostly great. The pull out sofa bed is not usable as it’s so uncomfortable. So then they charge $50/night for each rollaway. Thats not a good solution.
Reviewed on 28 Nov 2025

Pendry Chicago
Downtown Chicago
Price was €892, price is now €654 per person
€654
per person
1 Feb - 6 Feb
found 4 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I thoroughly enjoyed my time at Pendry Chicago. I stayed in a tower king room. I originally was going to stay in a suite but the normal king room was very spacious for one person. The valet service was pretty quick and the valets were all very nice. The front desk clerk was extremely helpful and professional. I loved staying right on Michigan Ave and within walking distance to so many things. I read some reviews saying safety was a concern but I didn’t experience any safety issues. They lock the doors on Michigan Ave after a certain point to keep the flow of traffic thru a better monitored entrance. I also took an evening(beginning around 9:30pm) stroll around Millennium Park, down to Buckingham fountain and back up Michigan Ave to the river and the surroundings blocks around the hotel. At no point did I feel unsafe and would highly recommend this hotel to anyone coming to Chicago. The location is fantastic, the employees are amazing and the rooms are comfy. What more could you ask for?
Reviewed on 26 Nov 2025
Top hotels in Greenwood

Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is €168 per night from 14 Dec to 15 Dec
€168
14 Dec - 15 Dec
includes taxes & fees
8.6/10 Excellent! (3,039 reviews)
Yes the room was clean nice and cozy
Reviewed on 17 Nov 2025

Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is €108 per night from 30 Nov to 1 Dec
€108
30 Nov - 1 Dec
includes taxes & fees
8.4/10 Very Good! (1,664 reviews)
All staff were great and kind to us except one. Austin at the waterfront bar. He was rude, expected us to know what we wanted to order the second we sat down. Rolled his eyes, processed to ignore us and served/check on other customers. When we asked him to break a $20 he again rolled his eyes. The ...
Reviewed on 23 Nov 2025

Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is €94 per night from 16 Dec to 17 Dec
€94
16 Dec - 17 Dec
includes taxes & fees
9/10 Wonderful! (1,323 reviews)
Excellent staff great location! Really loved this property!
Reviewed on 24 Nov 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.
