
Monticello Holidays
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Top Flight + Hotel Deals in Monticello
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €2,026, price is now €1,429 per person
€1,429
per person
23 May - 30 May
found 3 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
8.2/10 Very Good! (2,628 reviews)
Room was slightly small and there was no microwave. But for the most part enjoyed my stay.
Reviewed on 15 Apr 2026


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €2,598, price is now €1,766 per person
€1,766
per person
23 May - 30 May
found 3 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,463 reviews)
Beautiful new hotel with amazing views but there are zero amenities after 8pm. No food or drinks after 8pm and you are on an island physically so hard to leave and get anything. Don’t arrive hungry and certainly don’t expect to hang in a hotel bar. We asked for a connected room and they did not offer this (didn’t see like they tried as the hotel did not feel full). It was a waste of money to get a connecting room. Staff did not seem interested in problem solving.
Reviewed on 16 Apr 2026

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was €2,402, price is now €1,677 per person
€1,677
per person
23 May - 30 May
found 3 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on 14 Apr 2026
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! (157 reviews)
The host was super great an massaged me early with all the information I needed. They even offered dining recommendations. The house slept 10 and we had ample towels and toilet paper. The house is super cute! The only downside, the driveway is a little steep up to the house, so we were glad it didn't ...
Reviewed on 27 Jan 2026

Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is €91 per night from 19 Apr to 20 Apr
€91
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
Yes
Reviewed on 17 Apr 2026

Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
The price is €82 per night from 19 Apr to 20 Apr
€82
19 Apr - 20 Apr
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
Breakfast is good for the rate
Reviewed on 16 Apr 2026
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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