Monticello Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Monticello Flight & Hotel Packages

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
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Excellent location and property

Reviewed on 16 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The location is great, with a fantastic staff and an easy check-in process. I can walk to almost everything, and the bus station is right next to the door.

Reviewed on 16 Jul, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
It’s super convenient bc it’s on the pier but beware it’s connected so it’s not its own building. Still we felt safe and it was very clean

Reviewed on 16 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Family of 6 got two rooms near one another on the same floor. A wonderful property in a great location. We loved it

Reviewed on 16 Jul, 2025

Top hotels in Monticello

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 S$123 per night from 11 Aug to 12 Aug
S$123
11 Aug - 12 Aug
includes taxes & fees
8.6/10 Excellent! (1,162 reviews)
"Staff was friendly and efficient at handling check-in. Room was clean, bed comfortable, bathroom well-supplied."

Reviewed on 14 Jul, 2025

AmericInn by Wyndham Madison West
Baymont Inn & Suites by Wyndham Madison

Baymont Inn & Suites by Wyndham Madison

2.5 out of 5
2810 Coho Street, Madison, WI
Fully refundableReserve now, pay when you stay
The price is S$95 per night from 14 Aug to 15 Aug
S$95
14 Aug - 15 Aug
includes taxes & fees
7.2/10 Good! (1,563 reviews)
"."

Reviewed on 11 Jul, 2025

Baymont Inn & Suites by Wyndham Madison
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
The price is S$126 per night from 29 Jul to 30 Jul
S$126
29 Jul - 30 Jul
includes taxes & fees
8.6/10 Excellent! (1,176 reviews)
Very friendly, a bit run down
"We were in town for a wedding and this location worked best for us. We really liked the suite layout, with a door on the bedroom and a pull out couch in the other room. It wasn't fancy, but perfectly acceptable. Some minor cosmetic issues like cracked paint high on a wall in the bedroom. Some of ..."

Reviewed on 12 Jul, 2025

Best Western West Towne Suites
See all 155 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 S$437 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.

* 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.