Monticello Holidays
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Top Flight + Hotel Deals in Monticello
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)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on 1 Dec 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 Monticello
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello WI
10/10 Exceptional! (156 reviews)
Nice and clean. Close to town, but out in the country with a beautiful backyard with a fire pit.
Reviewed on 3 Nov 2025
Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is €59 per night from 5 Dec to 6 Dec
€59
5 Dec - 6 Dec
includes taxes & fees
9/10 Wonderful! (1,019 reviews)
Nice place to stay with the family.
Reviewed on 27 Nov 2025
Baymont Inn & Suites by Wyndham Madison
2810 Coho Street Madison WI
Fully refundableReserve now, pay when you stay
The price is €51 per night from 30 Dec to 31 Dec
€51
30 Dec - 31 Dec
includes taxes & fees
7.2/10 Good! (1,511 reviews)
Room wa clean but had a bad smell
Reviewed on 23 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
