Monticello Vacations from $144

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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.

The Latest Monticello vacation packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $313, price is now $144 per person
$144
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Everything was perfect

Reviewed on Nov 12, 2025

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $668, price is now $334 per person
$334
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Best location to stay

Reviewed on Oct 25, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $384, price is now $196 per person
$196
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.

Reviewed on Nov 12, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Price was $526, price is now $275 per person
$275
per person
Dec 31 - Jan 3
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (154 reviews)
Beautiful place, friendly staff. We loved the restaurant.

Reviewed on Nov 1, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $493, price is now $261 per person
$261
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on Nov 9, 2025

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Monticello Hotel Deals

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Monticello
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 Nov 3, 2025

Get rates
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Jaggi Swiss Gasthaus

Jaggi Swiss Gasthaus

Monticello
9.8/10 Exceptional! (43 reviews)
My husband and I had a great time. Our rental was perfect in every way! It was cozy and comfortable. Our hostess, Annamarie, was very hospitable. When we arrived, we found a complimentary bottle of wine, 2 mini apple pies and other goodies. We picked out this area to visit the New Glarus brewery, ...

Reviewed on Oct 26, 2025

Get rates
Jaggi Swiss Gasthaus
Best Western West Towne Suites

Best Western West Towne Suites

2.5 out of 5
650 Grand Canyon Dr, Madison, WI
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $88 total per night from Nov 30 to Dec 1
$88 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,183 reviews)
Yes

Reviewed on Oct 31, 2025

Best Western West Towne Suites
See all 150 properties in Monticello
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.

Find the Best Monticello Vacation Packages

Monticello Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Population
1,250
Top Sights
New Glarus Brewing Company, Minhas Craft Brewery and New Glarus Woods State Park

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Frequently asked questions

How much does a Monticello vacation package cost?
You can snap up a vacation package to this destination from $144 on Expedia. But how much your vacation to Monticello costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Monticello?
If you're hoping to book a cheap Monticello vacation package, consider visiting in November, December and January. You'll typically find better rates on flights and accommodations during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Monticello?
The ideal length for your Monticello vacation depends on what you'd like to see. Typically, a few days to a week will give you time to hit all the main attractions and discover some hidden treasures along the way.
How to find the best Monticello package deals?
Landing a cheap Monticello package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Monticello package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
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 hotels individually. Better still, you can tailor your Monticello getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Monticello?
Secure incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Monticello getaway.
Does Expedia offer Book Now, Pay Later Monticello vacation packages?
Your Monticello getaway should be an escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.