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.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,113, price is now CA $722 per person
CA $722
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Room was great, the staff and concierge exceeded expectations!
Reviewed on Feb 15, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,266, price is now CA $815 per person
CA $815
per person
Apr 21 - Apr 25
just found
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
Viceroy Chicago
Downtown Chicago
Price was CA $1,081, price is now CA $835 per person
CA $835
per person
Apr 8 - Apr 11
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
We stayed at the Viceroy Chicago last night and had a wonderful experience. The hotel is stylish, comfortable, and feels thoughtfully designed in every detail. The staff was warm and welcoming from the moment we arrived, and the service throughout our stay was excellent. Our room was spotless with a great layout, and the overall atmosphere of the hotel made it easy to relax and enjoy the night. A really lovely stay—highly recommend.
Reviewed on Feb 15, 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 $93 per night from Feb 23 to Feb 24
CA $93
CA $108 total
Feb 23 - Feb 24
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
No comment
Reviewed on Feb 16, 2026
Baymont Inn & Suites by Wyndham Madison
2810 Coho Street Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $69 per night from Mar 18 to Mar 19
CA $69
CA $80 total
Mar 18 - Mar 19
includes taxes & fees
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.
