Kendall County Vacation Packages
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Your Kendall County Vacation
Our Kendall County vacation packages make it a cinch to discover this alluring destination. From its walking trails to all its other appealing highlights, there are endless reasons to pack your bags and go. Get your trip to Kendall County off to a great start by experiencing its most famous cities. Oswego is one you shouldn't miss. Expedia is your one-stop shop for organizing your Kendall County vacation. From hotels and flights, to activities and more, we know how to create a travel experience like no other.
Top Kendall County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,404
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Free upgrade was amazing and staff were even better. Thank you.
Reviewed on Oct 6, 2026
Kendall County Hotel Deals
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
CA $83
CA $92 total
Nov 5 - Nov 6
includes taxes & fees
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
CA $133
CA $148 total
Oct 7 - Oct 8
includes taxes & fees
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
CA $149
CA $165 total
Nov 1 - Nov 2
includes taxes & fees
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 County vacation package cost?
Starting from as low as CA $855, you can handcraft your own Kendall County package the way you want. Simply combine hotels, flights and rental cars and we'll reward you with discounts.
How do I get a cheap travel package to Kendall County?
Our Kendall County vacation packages promise plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities) into one neat package. But great bargains are just the beginning of your next big adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotels around the world to select from. No matter your budget, there's a package with your name on it.
What are the top hotels in Kendall County?
If you're headed to Oswego, you can't go past Best Western Chicago - Downers Grove and Motel 6 Naperville, IL. Both are comfortable bases for exploring this exciting Kendall County city.
How far in advance should I book my Kendall County vacation?
Savvy travelers will likely want to book early. You can generally compare international airfares on Expedia up to 12 months before your flight. If you've left booking to the last minute, don't stress. Budget prices sometimes become available just weeks prior to departure.
What does an Expedia Kendall County travel package include?
That depends on you. You can pick from a variety of Kendall County bundles, such as a flight, hotel and rental car. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like activities and tours. Whatever your dream Kendall County trip looks like, you're sure to save!
What should I know before booking a Kendall County travel package?
Whether it's adventure or relaxation you're seeking, a Kendall County vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Kendall County Expedia vacation package?
With a vacation package, you're always in charge. Whether you're hoping to fly to Kendall County in economy or business class, simply select from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Kendall County vacation package?
Because we understand life can be unpredictable, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
Stay near popular Kendall County attractions
Photo by travelbug
Farnsworth House
6.0/10 (3 reviews)
You can learn about the history of Plano with a visit to Farnsworth House. Stroll along the riverfront or experience the art scene in this family-friendly area.
Hudson Crossing Park
6.0/10 (4 reviews)
Explore the great outdoors at Hudson Crossing Park, a lovely green space in Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries.
Raging Waves Waterpark
8.6/10 (50 reviews)
Take the family on an outing to Raging Waves Waterpark during your trip to Yorkville. While you're here, you can savor the top-notch restaurants.
Fox Valley Winery
6.8/10 (5 reviews)
You can enjoy a tasting or tour at Fox Valley Winery during your travels to Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries.
Keller's Farmstand
Enjoy a fun-filled day at Keller's Farmstand as part of your trip to Oswego. While in this family-friendly area, you can enjoy the restaurants.
Cedardell Golf Club
Enjoy a round of golf in Plano at Cedardell Golf Club. While in this family-friendly area, you can enjoy the coffeehouses.
What to do in Kendall County
Private Deep Dish Pizza or Pasta Making Class Near Chicago
CA $138
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
