Monticello Vacations

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Find the Best Monticello Vacation Packages

Monticello Hotel Deals

Best Western Plus Brandywine Inn & Suites

Best Western Plus Brandywine Inn & Suites

2.5 out of 5
304 S 6th Street Monticello IN
Fully refundableReserve now, pay when you stay
The price is AED 397 per night from Mar 2 to Mar 3
AED 397
AED 444 total
2 Mar - 3 Mar
includes taxes & fees
8.2/10 Very Good! (665 reviews)
Staff was friendly. The room was very run down and looked nothing like the pictures.

Reviewed on 27 February 2026

Best Western Plus Brandywine Inn & Suites
Blue Door Cottages

Blue Door Cottages

2 out of 5
5312 N. West Shafer Drive Monticello IN
The price is AED 384 per night from Mar 8 to Mar 9
AED 384
AED 430 total
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (99 reviews)
Arrived and the bed our kids were supposed to sleep on was broken and it was unusable. Refrigerator was rusted. Blinds broken in main bedroom. Flooring completely falling apart. Spider webs everywhere. Listing showed it on the lake, it was across a very busy street from the property. This listing ...

Reviewed on 20 October 2025

Blue Door Cottages
Lake Freeman house w/boat dock... Minutes from Indiana Beach/Lake Shafer

Lake Freeman house w/boat dock... Minutes from Indiana Beach/Lake Shafer

Monticello IN
10/10 Exceptional! (60 reviews)
Good accomodations and close to Indiana beach.

Reviewed on 7 September 2025

Lake Freeman house w/boat dock... Minutes from Indiana Beach/Lake Shafer
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 do I find cheap flights to Monticello that have flexible change policies?
Search for cheap flights to Monticello, then select "No change fee" underneath the "Flexible change policies" heading. It's as easy as that. We know that travel plans change and flexibility is important, so you can book with confidence with Expedia.
Which airlines fly to Monticello?
Whenever and wherever you want to travel, these airlines will take you comfortably to or near Monticello:

  • United Airlines - 13,638 flights to or near Monticello each month, including 13,005 flights to O'Hare Intl. Airport (ORD) and 629 to Indianapolis Intl. Airport (IND) per month.
  • American Airlines - 11,219 flights to or near Monticello each month, including 10,036 flights to O'Hare Intl. Airport (ORD) and 1,183 to Indianapolis Intl. Airport (IND) per month.

How can I find cheap tickets to Monticello?
An effective strategy for nabbing cheap fares is to be flexible with your dates. Start by searching for your flight to Monticello, then click on the "flexible dates" box to compare prices for nearby days. Want another good tip? Book in advance. To give you an idea of fares, was the best price for a flight to Monticello in the last seven days.
How much is a flight to Monticello?
If you were traveling one way from (), you could've scored a low-cost fare for in the last seven days. Round-trip journeys to Monticello ranged from to during this same period.
What are the most popular airports to fly into in Monticello?
Your place of departure and the carrier you're traveling with will determine which of these leading Monticello airports you'll fly into:

  • O'Hare Intl. Airport (ORD) - 26,484 flights per month.
  • Midway Intl. Airport (MDW) - 6,439 flights per month.
  • Indianapolis Intl. Airport (IND) - 3,680 flights per month.

When is the cheapest time to fly to Monticello?
Leave for Monticello earlier in the week and you'll usually be rewarded with lower-priced fares. Tuesday is typically the cheapest day to fly out, closely followed by Monday. If you want to avoid the priciest flights, give Saturdays a wide berth.
How much is a plane ticket to Monticello?
In the last seven days, flights to Monticello varied between and . Prices depend on a number of things, particularly the time of departure, airline, cabin class and when you make your booking.
What months are the cheapest to book a flight to Monticello?
An inexpensive month to bag a top deal to Monticello is February, while prices are at their highest in December. Give this month a miss if you're on a budget.
How long is a flight to Monticello?
Whether or not you'll have time to binge-watch your favorite series depends on where you're flying from in the USA. To make organizing your trip a little easier, here are the average flight times for some sought-after domestic routes to Monticello:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 37 minutes
  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 34 minutes
  • Phoenix, AZ (PHX-Sky Harbor Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 17 minutes