Monticello Vacations from $470

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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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,482, price is now $470 per person
$470
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Price was $1,108, price is now $704 per person
$704
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $856, price is now $557 per person
$557
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before you arrive! There is no lobby, no where in the hotel to hang, no vibe. You are literally staying in a condo and have to exit the building and walk a few blocks to be anywhere. Maybe this is the new hotel experience, but for me, I still like some ammenities. The room was fine T

Reviewed on Nov 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $795, price is now $519 per person
$519
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $722, price is now $485 per person
$485
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

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Monticello Hotel Deals

Jaggi Swiss Gasthaus

Jaggi Swiss Gasthaus

Monticello WI
Get rates
Jaggi Swiss Gasthaus
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 WI
10/10 Exceptional! (170 reviews)
"Great property located far enough out of town to be secluded yet close enough to activities. Host was super and place was perfect for our weekend getaway."

Reviewed on Oct 18, 2026

Get rates
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $73 total per night from Dec 6 to Dec 7
$73 total
Dec 6 - Dec 7
Total with taxes and fees
AmericInn by Wyndham Madison West
See all 171 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 $470 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.