Monticello Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Monticello Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
S$667
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Room was standard, close to millennium park, very helpful staff, & yummy restaurant!
Reviewed on 13 Oct, 2026
Sentral Michigan Avenue
Downtown Chicago
S$684
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,344 reviews)
Best part of this place is the location. Didn’t take any Ubers just walked everywhere, and let’s not forget the in-unit laundry. Definitely would stay here again!
Reviewed on 12 Oct, 2026
Omni Chicago Hotel
Downtown Chicago
S$794
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (2,097 reviews)
Great stay. Perfect location, we walked everywhere. The rooms are a little out dated and you can hear the city noise and any noise outside your room very well. We were able to leave our bags and explore the city before our flight. I would definitely stay here again.
Reviewed on 13 Oct, 2026
Top hotels in Monticello
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
S$102
1 Nov - 2 Nov
includes taxes & fees
9/10 Wonderful! (1,374 reviews)
"The shower curtain is about 1-2 in above the ground. It's right over the lip to outside the tub. Water from the shower dripped on the curtain and onto the floor and created a puddle"
Reviewed on 13 Oct, 2026
Best Western West Towne Suites
650 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
S$113
25 Oct - 26 Oct
includes taxes & fees
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
S$124
5 Nov - 6 Nov
includes taxes & fees
9.4/10 Exceptional! (1,114 reviews)
"It was our first time at a Tru by Hilton and we were impressed with the price, the clean fresh lobby and rooms, the evening staff at the desk, and a huge tv in our room! Will definitely visit again."
Reviewed on 13 Oct, 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.
Frequently asked questions
How much does a Monticello holiday package cost?
You can snap up a holiday package to this destination from S$614 on Expedia. But how much your holiday to Monticello costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Monticello?
To pick up cheap Monticello holiday packages, organise your getaway outside of busy periods like public holidays and major festivals. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Monticello?
The ideal length of your Monticello holiday depends on what you'd like to see. Usually, a handful of days to a week will give you time to hit all the major attractions and explore 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Monticello holiday as a package?
An Expedia holiday 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 holiday 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.
How to plan a trip to Monticello?
- Choose when to travel: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to holiday in Monticello.
- Set a budget: Factor in expenses like transportation, flights and meals when working out how much to set aside for your trip to Monticello. Then, pick a hotel that fits your budget, whether that's a wallet-friendly stay or a more luxurious getaway.
- Decide your trip length: Consider how much time you want to spend exploring Monticello. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customised Monticello holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
