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.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,702
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
They charge a facilities fee which is about 20 bucks a night for the amenities. I generally don't have a problem with that as it includes breakfast. BUT, I was annoyed that in the hotel gym (which isn't bad), the bikes had some problems. It's a slight nitpick, admittedly, but that's what it is. The hotel is very close to transit and the LOOP which is the main area of Chicago. Staff were amazing and helpful, the breakfast was very filling. The gym has weights that go up to 20KG, which is pretty nice and they do have those gymbro slogans on the walls which is kind of fun.
Reviewed on Aug 22, 2026
The Talbott, Autograph Collection
Downtown Chicago
CA $1,447
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
CA $1,265
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.
Reviewed on Aug 21, 2026
Kendall County Hotel Deals
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
CA $87
CA $97 total
Aug 30 - Aug 31
includes taxes & fees
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
CA $77
CA $86 total
Sep 20 - Sep 21
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 $179
CA $199 total
Aug 30 - Aug 31
includes taxes & fees
8.2/10 Very good! (1,775 reviews)
"We had a pleasant stay. We liked the breakfast options."
Reviewed on Aug 21, 2026
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 $1,099, 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
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.
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.
Richard E Klatt Memorial Field
Explore the great outdoors at Richard E Klatt Memorial Field, a lovely green space in Plano. 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 $139
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
