Timberlane Vacations from $401

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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.

The Latest Timberlane Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 16 - Dec 19

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,161 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $609
    $401
    per traveler
    found 1 day ago
    Pendry Chicago
  • Dec 20 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,873 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,483
    $471
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Dec 24 - Dec 29

    The Emily Hotel + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,356 reviews)
    "Staff was friendly and the room was clean"
    Reviewed November 3, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $830
    $508
    per traveler
    found 1 day ago
    The Emily Hotel
  • Jan 5 - Jan 10

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (601 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $640
    $404
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • Jan 22 - Jan 25

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,641 reviews)
    "We thoroughly enjoyed our stay at the Riu Hotel. The location was fantastic. You could go shopping or walk to the lakefront in 5 minutes. The rooms were modern and immaculate. The breakfast was included in our reservation and was great. We were also able to enjoy the rooftop bar with a heater. We would definitely recommend staying here"
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $720
    $475
    per traveler
    found 1 day ago
    Hotel Riu Plaza 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?

You'll find cheap prices from $401 on Expedia for your Timberlane getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Timberlane costs.

What are the cheapest months to go to Timberlane?

December, January and February are great times to look for cheap Timberlane vacation packages. Opting to travel in less busy periods means you can typically find better prices on accommodations and flights.

How many days is enough for Timberlane?

With a well-organized travel plan, you can easily visit the top Timberlane sights in a few days. But if you want to discover lesser-known spots or go on day tours, think about booking your Timberlane vacation for longer.

How to find the best Timberlane package deals?

Use Expedia's handy filters to find some of the best Timberlane package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Timberlane package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.

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

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Timberlane vacation by choosing your preferred airline, accommodation type and car class.

When to book a vacation package to Timberlane?

If you've got your Timberlane vacation dates confirmed, book early to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.

Does Expedia offer Book Now, Pay Later Timberlane vacation packages?

Your Timberlane trip should be an escape from your busy life, not a source of money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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