Monticello Holidays from £1,164

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Your Monticello Holiday

Amazing adventures await when you book a Monticello holiday package. Whether you're a history buff, foodie or just a traveller 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 holiday is a couple of clicks away with Expedia.

Top Monticello Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,742, price is now £1,164 per person
£1,164
per person
29 Sept - 6 Oct
found 17 hours ago
Return flight included
Edinburgh (EDI) 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

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,143, price is now £1,406 per person
£1,406
per person
29 Sept - 6 Oct
found 17 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (501 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

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,830, price is now £1,952 per person
£1,952
per person
29 Sept - 6 Oct
found 17 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
Trump is the best in town for families. Staff is awesome and pool is great. Very walkable. We go every summer

Reviewed on 16 Jul 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,688, price is now £1,863 per person
£1,863
per person
20 Sept - 23 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
amazing!

Reviewed on 16 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,893, price is now £1,347 per person
£1,347
per person
29 Sept - 6 Oct
found 17 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)

Monticello Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Population
1,250
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
New Glarus Brewing Company, Minhas Craft Brewery and New Glarus Woods State Park

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 £68 per night from 26 Jul to 27 Jul
£68
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (1,239 reviews)
"Friendly staff, excellent breakfast, and room was very clean and bed was very comfortable."

Reviewed on 17 Jul 2026

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 £78 per night from 2 Aug to 3 Aug
£78
2 Aug - 3 Aug
includes taxes & fees
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Monticello travel package cost?
From just £1,164. Yes, you read that right. Our Monticello travel packages are an awesome way to stretch your budget. Bundle your preferred hotels, flights and car rentals and get out and explore this exciting destination.
If I'm not able to travel, can I cancel my Monticello travel package?
Because we know life is full of surprises, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you've booked your Monticello travel package in the last 24 hours, you may be able to change or cancel it for no charge. Your hotel, airline or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Monticello?
If you love bargains, combine your bookings into a Monticello travel package. Whether you're chasing hotels, flights, rental cars or activities, you can book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has more than 550 air carriers and 1,000,000 properties across the globe to choose from. Fly with who you prefer, stay where you like and save a bundle — now that's the perfect getaway!
Does Expedia offer Book Now, Pay Later Monticello holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan best suited to your needs during checkout and take the stress out of budgeting for your next trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that work for all budget sizes, so you can take that well-earned holiday now.
  • Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you want to jump on an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you get what you want.

What are the top hotels in Monticello?
Make a reservation at Harbour Shores on Lake Geneva. It's one of this neighbourhood's most sought-after hotels. Another highly rated option in Monticello is Mt. Olympus Water & Theme Park Resort.
How far in advance should I book my Monticello holiday?
It's always wise to book early. Airlines usually advertise flight tickets around a year prior to departure, and this is a fantastic opportunity to pick up some of the cheapest prices. Just been told you need to take your holiday time in a few weeks? No problem! Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Monticello travel package include?
From hotels and airfares to car rentals, Expedia can help you shape a Monticello package that works for you. Holidaying for a week or two? Consider a hotel, rental car and flight bundle. If you're taking a short break, a hotel and airfare deal could be more your style. Activities can also be added after you've booked. Our travel packages make it a breeze to plan and save.
What should I know before booking a Monticello travel package?
You'll land amazing savings when you combine your flights, hotels and rental cars into a package. Not only that, booking everything in one place simply makes planning easier. So why waste money or time? Whether you're organising an upscale romantic escape or a budget family adventure, explore our package deals today.
Can I choose my airline with a Monticello Expedia travel package?
With a travel package, you're always in charge. Whether you're looking to fly to Monticello in coach or business class, simply select from the available airline options. Expedia has access to over 550 airline partners all over the world.

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. Flight-inclusive packages are ATOL protected.