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 vacation destinations in Kendall County

FlightsFlightsHotelsHotels

Oswego

Oswego

Top Kendall County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,113, price is now CA $722 per person
CA $722
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Room was great, the staff and concierge exceeded expectations!

Reviewed on Feb 15, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,266, price is now CA $815 per person
CA $815
per person
Apr 21 - Apr 25
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,436, price is now CA $973 per person
CA $973
per person
May 6 - May 10
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The room was excellent

Reviewed on Feb 16, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,193, price is now CA $894 per person
CA $894
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Everything was amazing

Reviewed on Feb 17, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,081, price is now CA $835 per person
CA $835
per person
Apr 8 - Apr 11
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
We stayed at the Viceroy Chicago last night and had a wonderful experience. The hotel is stylish, comfortable, and feels thoughtfully designed in every detail. The staff was warm and welcoming from the moment we arrived, and the service throughout our stay was excellent. Our room was spotless with a great layout, and the overall atmosphere of the hotel made it easy to relax and enjoy the night. A really lovely stay—highly recommend.

Reviewed on Feb 15, 2026

The Annual Vacation Sale

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Kendall County Hotel Deals

Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Feb 18 to Feb 19
CA $95
CA $105 total
Feb 18 - Feb 19
includes taxes & fees
7/10 Good! (1,430 reviews)
yes

Reviewed on Feb 13, 2026

Chicago Club Inn & Suites
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
The price is CA $122 per night from Feb 18 to Feb 19
CA $122
CA $163 total
Feb 18 - Feb 19
includes taxes & fees
8.4/10 Very Good! (1,408 reviews)
Great stay and service! Will be back again.

Reviewed on Feb 16, 2026

The Champagne Lodge & Luxury Suites
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Feb 24 to Feb 25
CA $111
CA $123 total
Feb 24 - Feb 25
includes taxes & fees
7.8/10 Good! (1,237 reviews)
Great place to stay!

Reviewed on Feb 14, 2026

DoubleTree by Hilton Lisle Naperville
See all 911 properties in Kendall County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Kendall County vacation package cost?
Starting from as low as CA $722, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.