Monticello Holidays

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Top Flight + Hotel Deals in Monticello

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was €801, price is now €489 per person
€489
per person
7 Sept - 12 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
Clean, rustic, great. Will visit again.

Reviewed on 17 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,024, price is now €649 per person
€649
per person
24 Sept - 29 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
decent property - definitely shows better in photos. that was probably my biggest let-down. also, only staying one night, the room cleaner came into our room at 8 am despite check out time not being until noon. my kid was still asleep and I was in the shower. front desk service level definitely elevated the rating.

Reviewed on 17 Jul 2026

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was €815, price is now €531 per person
€531
per person
7 Sept - 12 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,363 reviews)
Very clean room. The front desk person was extremely helpful in giving directions on how to get valet parking.

Reviewed on 17 Jul 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,014, price is now €663 per person
€663
per person
20 Sept - 24 Sept
found 5 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €957, price is now €645 per person
€645
per person
20 Sept - 24 Sept
found 5 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on 14 Jul 2026

Top hotels in Monticello

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! (162 reviews)
"We had a wonderful stay! I would love to come back and stay again. We loved the house. Everything was comfortable. Communication was excellent."

Reviewed on 13 Jul 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
The price is €76 per night from 30 Jul to 31 Jul
€76
30 Jul - 31 Jul
includes taxes & fees
AmericInn by Wyndham Madison West
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

2.5 out of 5
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is €82 per night from 11 Aug to 12 Aug
€82
11 Aug - 12 Aug
includes taxes & fees
9.4/10 Exceptional! (1,042 reviews)
"Everything was just what we needed for our stay. No microwave in the room, but otherwise a good, low-budget stay."

Reviewed on 16 Jul 2026

Tru by Hilton Madison West, WI
See all 163 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.

Frequently asked questions

How much does a Monticello holiday package cost?
You can snap up a holiday package to this destination from €489 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.