
Leland Holidays
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Top Flight + Hotel Deals in Leland
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 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
Price was €2,929, price is now €2,019 per person
€2,019
per person
1 Feb - 6 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

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)
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 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I had an amazing stay at The Pendry Chicago. The hotel is gorgeous, modern, and feels truly high-end without trying too hard. My room was super clean, comfortable, and quiet—honestly one of the best sleep setups I’ve had in a hotel.
The staff made the whole experience even better. Everyone I talked to was friendly, helpful, and actually seemed to enjoy their jobs. The lobby bar and restaurant were great too, and the whole vibe of the place is relaxed but still upscale.
The location made it easy to get around the city, but I kept finding myself wanting to head back early just to enjoy the hotel.
I’d definitely stay here again and recommend it to anyone visiting Chicago.
Reviewed on 30 Nov 2025
Top hotels in Leland

Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
Fully refundableReserve now, pay when you stay
The price is €112 per night from 2 Dec to 3 Dec
€112
2 Dec - 3 Dec
includes taxes & fees
7.2/10 Good! (1,010 reviews)
Clean place, good staff, good time
Reviewed on 26 Nov 2025

Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is €112 per night from 7 Dec to 8 Dec
€112
7 Dec - 8 Dec
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
always a sure thing for clean room and bathroom and overall building + very comfy bed + best breakfast of any Hampton Inn that I stay in — by far...
Reviewed on 28 Nov 2025

Holiday Inn Express & Suites Yorkville by IHG
577 E KENDALL DRIVE Yorkville IL
Fully refundable
The price is €73 per night from 7 Dec to 8 Dec
€73
7 Dec - 8 Dec
includes taxes & fees
8.2/10 Very Good! (617 reviews)
This was a gem! I’m initially from this area and was visiting some family. I was surprised to see this hotel nearby. My husband and I got accommodations on a weekend evening that were affordable and clean. Our room was updated, the bathroom was large, the tv functional, and the morning complimentary ...
Reviewed on 28 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
