Timberlane Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Timberlane Vacation

When a city break is calling, answer it with a Timberlane vacation package. With all your travel needs in place before you go, all you have to do here is focus on enjoying yourself. Make your trip to Timberlane even more fulfilling by including some sightseeing. Rock Cut State Park, Rivets Stadium and McEachran Homestead Winery are some of the top attractions worth exploring. Don't put off visiting this city any longer. The ultimate Timberlane vacation is just a few clicks away with Expedia.

Top Timberlane vacation deals

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

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $914
    CA $671
    per traveller
    found 6 hours ago
    Le Méridien Essex Chicago
  • Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,009 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    Save 100% on your flight
    CA $1,899
    CA $1,337
    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 (1,885 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,107
    CA $794
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,801
    CA $1,316
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • Jan 21 - Jan 24

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,344
    CA $984
    per traveller
    found 1 day ago
    Pendry Chicago

Timberlane 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 Timberlane vacation package cost?

Offering great value package deals from CA $671 on Expedia, you'll be pleasantly surprised at how much a vacation to Timberlane costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Timberlane?

January, February and November are the best times to search for cheap Timberlane vacation packages. Travelling in quieter periods means you can generally find better prices on accommodations and flights.

How many days is enough for Timberlane?

Usually, a handful of days is enough to visit the top sights during your Timberlane vacation. But if you want to have time to chill out or go on day trips, think about extending your itinerary.

How to find the best Timberlane package deals?

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

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

You can enjoy significant savings on your Timberlane break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Timberlane?

Secure fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Timberlane getaway.

How to plan a trip to Timberlane?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to visit Timberlane.
  2. Budget wisely: Besides the cost of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Timberlane.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to experience in Timberlane. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Timberlane 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.