Monticello Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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Your Monticello Vacation

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

Top Monticello vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 24

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (194 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,195
    CA $943
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • Jan 8 - Jan 11

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,008 reviews)
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $2,118
    CA $1,439
    per traveller
    found 6 hours ago
    The Peninsula Chicago
  • Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,880 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,322
    CA $979
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Sofitel Chicago Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (2,679 reviews)
    "Great room, rates and staff"
    Reviewed November 7, 2026
    Roundtrip • Calgary (YYC) - Chicago (ORD)
    YYC - ORD • Nonstop ORD - YYC • 1 stop
    CA $1,490
    CA $1,174
    per traveller
    found 18 hours ago
    Sofitel Chicago Magnificent Mile
  • Jan 8 - Jan 11

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    8.8/10 - Excellent (2,335 reviews)
    "I had an amazing view and excellent service."
    Reviewed November 6, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,238
    CA $977
    per traveller
    found 6 hours ago
    Fairmont Chicago at Millennium Park

Monticello Hotel Deals

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 vacation package cost?

You'll find cheap prices from CA $943 on Expedia for your Monticello escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Monticello costs.

What are the cheapest months to go to Monticello?

The off-season is the best time to head to Monticello if you're hoping to keep costs down. Another tip for finding cheap Monticello vacation packages? Try to avoid public holidays and any major festivals or events.

How many days is enough for Monticello?

With a well-organized travel plan, you can easily hit the top Monticello attractions in a few days. But if you prefer to discover hidden spots or take day trips, consider booking your Monticello vacation for longer.

How to find the best Monticello package deals?

Start your search for a Monticello package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Monticello package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Monticello escape off to a flying start.

Is it cheaper to book a Monticello vacation as a package?

An Expedia vacation package could land you significant savings when compared to booking flights and stays separately. Better still, you can customize your Monticello getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.

When to book a vacation package to Monticello?

If you're considering an impromptu Monticello adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.

How to plan a trip to Monticello?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Monticello.
  2. Plan your budget wisely: On top of the cost of your stay, you should factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may arise during your trip to Monticello.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you'd like to experience in Monticello. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Monticello vacation package that brings all your bookings together.

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