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.
Pendry Chicago
Downtown Chicago
CA $1,071
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.
Reviewed on Sep 23, 2026
Ready to book your vacation to Monticello?
Monticello Hotel Deals
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello WI
10/10 Exceptional! (168 reviews)
"Great stay. Lots of room. Very comfortable stay. Very peaceful."
Reviewed on Sep 23, 2026
Jaggi Swiss Gasthaus
Monticello WI
10/10 Exceptional! (44 reviews)
"Host was lovely and very accommodating. Space was very cozy and provided everything I needed. Quick and beautiful drive into New Glarus and surrounding sights. The grounds are perfect and I hope to return in warmer months to enjoy the pool and lush property. Highly recommend!"
Reviewed on Nov 18, 2025
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
CA $98
CA $113 total
Oct 4 - Oct 5
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.
Frequently asked questions
How much does a Monticello vacation package cost?
You'll find cheap prices from CA $914 on Expedia for your Monticello escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Monticello costs.
What are the cheapest months to go to Monticello?
The off-season is the best time to head to Monticello if you're hoping to keep costs down. Another tip for finding cheap Monticello vacation packages? Try to avoid public holidays and any major festivals or events.
How many days is enough for Monticello?
With a well-organized travel plan, you can easily hit the top Monticello attractions in a few days. But if you prefer to discover hidden spots or take day trips, consider booking your Monticello vacation for longer.
How to find the best Monticello package deals?
Start your search for a Monticello package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Monticello package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Monticello escape off to a flying start.
Is it cheaper to book a Monticello vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays separately. Better still, you can customize your Monticello getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Monticello?
If you're considering an impromptu Monticello adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Monticello?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Monticello.
- Plan your budget wisely: On top of the cost of your stay, you should factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may arise during your trip to Monticello.
- Determine how many days away: Start by compiling a list of the attractions and activities you'd like to experience in Monticello. Then, estimate how long you'll need at each, including any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Monticello vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
