Grayslake Holidays
Photo by Richard Remington
- 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 Grayslake
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was €1,386, price is now €793 per person
€793
per person
5 Feb - 11 Feb
found 1 day 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
Save 100% on your flight
Price was €3,440, price is now €2,345 per person
€2,345
per person
5 Feb - 11 Feb
found 1 day 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
Pendry Chicago
Downtown Chicago
Price was €1,009, price is now €713 per person
€713
per person
5 Feb - 11 Feb
found 1 day 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
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 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Everything perfect , comfortable room , nice staff make out stay unforgettable.
Reviewed on 27 Nov 2025
Top hotels in Grayslake
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
Fully refundableReserve now, pay when you stay
The price is €83 per night from 14 Dec to 15 Dec
€83
14 Dec - 15 Dec
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
The room was clean. The woman at the front desk was very nice and helpful. I chose this hotel because it stated that it was only an 11 minute drive to the Naval RTC graduation. The drive was actually 25 minutes. Otherwise, nice hotel; I’d stay again.
Reviewed on 22 Nov 2025
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
Fully refundableReserve now, pay when you stay
The price is €107 per night from 7 Dec to 8 Dec
€107
7 Dec - 8 Dec
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
The hotel was clean, inviting and the staff was courteous. Unfortunately they have the skimpiest pillows I've ever seen. It was difficult to sleep on them. Also the sheets arent long enough to cover a king sized bed, do the bottom of the bed is weird.
Reviewed on 23 Nov 2025
Motel 6 Prospect Heights, IL
540 N Milwaukee Ave Prospect Heights IL
Fully refundableReserve now, pay when you stay
The price is €37 per night from 15 Dec to 16 Dec
€37
15 Dec - 16 Dec
includes taxes & fees
8/10 Very Good! (1,525 reviews)
clean rooms
Reviewed on 27 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.
