Kendall 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

Top Kendall 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 14 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 (1,881 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 1 day 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 (2,337 reviews)
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,238
    CA $977
    per traveller
    found 14 hours ago
    Fairmont Chicago at Millennium Park

Kendall 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 Kendall vacation package cost?

You'll find cheap prices from CA $864 on Expedia for your Kendall getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Kendall costs.

What are the cheapest months to go to Kendall?

Travel in the low or shoulder season and you're likely to score cheap Kendall vacation packages. Bear in mind that public holidays and major events and festivals can have an impact on prices, so do a little research before you go.

How many days is enough for Kendall?

Usually, a handful of days is enough to explore the top attractions during your Kendall vacation. However, if you'd like to have time to rest or go on day tours, think about extending your itinerary.

How to find the best Kendall package deals?

Bagging a cheap Kendall package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Kendall package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.

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

You can enjoy significant savings on your next Kendall getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Kendall?

Enjoy fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Kendall adventure.

How to plan a trip to Kendall?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred time of year and the activities available will also help you decide when to escape to Kendall.
  2. Set a budget: Factor in costs such as transportation, flights and meals when calculating how much to put aside for your trip to Kendall. Then, pick a hotel that works with your budget, whether that's a low-cost stay or a more luxurious getaway.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Kendall. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Kendall vacation package.

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