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 55 Chicago Downtown
Downtown Chicago
CA $1,136
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,577 reviews)
We stayed for one night for my birthday to do some sight seeing. The room was nice, the shower was AMAZING, and it was close to everything downtown.
Reviewed on Aug 20, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $6,031
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,393
per person
Oct 27 - Oct 31
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,152
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 2026
Kendall County Hotel Deals
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
CA $85
CA $95 total
Aug 31 - Sep 1
includes taxes & fees
6.4/10 (1,254 reviews)
"Run down and sketchy. Not a place is recommend."
Reviewed on Aug 20, 2026
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 $180
CA $200 total
Aug 23 - Aug 24
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 $1,136, 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.
