Monticello Vacation Packages
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Your Monticello Vacation
Amazing adventures await when you book a Monticello vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this vibrant city. New Glarus Brewing Company, Swiss Historical Village and Swissland Miniature Golf are just a few of the many sights worth visiting during your trip to Monticello. Don't delay your visit to this city any longer. The perfect Monticello vacation is a couple of clicks away with Expedia.
Top Monticello Vacation Deals
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Price was CA $1,056, price is now CA $718 per person
CA $718
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,955, price is now CA $1,149 per person
CA $1,149
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,179, price is now CA $763 per person
CA $763
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Loved the hotel and ambiance. My stay was truly amazing. I just wish they would’ve had an ice machine and microwaves inside the hotel . It would’ve been 5 stars if they had microwaves and ice. Also the receptionist attitude wasn’t the best. I didn’t feel very welcomed and seemed like she was just trying to rush me away.
Reviewed on Feb 26, 2026
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,317, price is now CA $951 per person
CA $951
per person
May 5 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.
Reviewed on Feb 26, 2026
Monticello Hotel Deals
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 Jan 27, 2026
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Mar 5 to Mar 6
CA $94
CA $108 total
Mar 5 - Mar 6
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
Good Location, very clean comfortable room. Staff at check in was super friendly.
Reviewed on Feb 26, 2026
Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Mar 2 to Mar 3
CA $100
CA $115 total
Mar 2 - Mar 3
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Consistent with other Hampton inn locations. The staff was, at both check in and check out, sincerely friendly.
Reviewed on Feb 25, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
