Title: Kendall County Vacation Packages & Trips 2025 from CA $724 | Expedia.ca [Kendall County Travel Guide](https://expedia.ca/Kendall-County.dx553248635976433381)[Kendall County Hotels](https://expedia.ca/Destinations-In-Kendall-County.d553248635976433381.Hotel-Destinations)[Vacation Rentals in Kendall County](https://expedia.ca/Destinations-In-Kendall-County.d553248635976433381.Vacation-Rental-Destinations)[Kendall County Car Rentals](https://expedia.ca/Destinations-In-Kendall-County.d553248635976433381.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/6186/2b367267-d22d-4742-8626-540c544b7491.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Kendall County Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 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 ### 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](https://www.expedia.ca/Oswego.d142441.Destination-Travel-Guides) 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. ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $724 per person Dec 30 - Jan 2 found 9 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) Excellent stay. The hotel staff is very courteous and helpful, and the location is great! Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=19PV2pgAjljVuJCn96RrG4045akwGRD67M4Yuh4OzYz6bXdB_TnfinACXP-5LW2i) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $824 per person Dec 23 - Dec 28 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=kDhtpFwUY77IpIJUdgP2xEJseRK2YP1TRDpx-p87kYagr8J7Kz5t7lkPntm9Dd23) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $887 per person Dec 23 - Dec 28 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (367 reviews) This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom. The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine. Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters. Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=kDhtpFwUY77IpIJUdgP2xEJseRK2YP1TRDpx-p87kYaMK00ZNHyHPlc-bq_PWnA8) ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,351 per person Dec 30 - Jan 2 found 9 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,004 reviews) Beautiful place and service Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&dealMarker=19PV2pgAjljVuJCn96RrG5Lx303KKYin3RS1k04KbvO5Njtcibah6TZF8kvJJ791) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,084 per person Dec 30 - Jan 2 found 9 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=19PV2pgAjljVuJCn96RrG5Lx303KKYin3RS1k04KbvOebjud0wlj8OFiqm6Bg1cv) ## Kendall County Hotel Deals ![Chicago Club Inn & Suites](https://images.trvl-media.com/lodging/1000000/10000/8500/8492/02be5769_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chicago Club Inn & Suites 630 Pasquinelli Dr, Westmont, IL Fully refundableReserve now, pay when you stay CA $95 CA $105 total Nov 30 - Dec 1 includes taxes & fees 7/10 Good! (1,309 reviews) Clean room Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%2F2025&selected=8492&PinnedHotelID=8492&HadPinnedHotel=true®ionId=553248635976433381) ![Motel 6 Naperville, IL](https://images.trvl-media.com/lodging/1000000/10000/9300/9225/4ecd9a2e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 Naperville, IL 1585 Naperville Wheaton Road, Naperville, IL Fully refundable CA $69 CA $77 total Nov 10 - Nov 11 includes taxes & fees 7.8/10 Good! (1,098 reviews) hallways were pretty dirty (but room was fine) Reviewed on Oct 22, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&selected=9225&PinnedHotelID=9225&HadPinnedHotel=true®ionId=553248635976433381) ![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/w3838h2556x2y3-00664b38_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay Plus Hotel by Best Western Chicago Lombard 222 E 22nd Street, Lombard, IL Fully refundableReserve now, pay when you stay CA $117 CA $129 total Nov 5 - Nov 6 includes taxes & fees 8.8/10 Excellent! (2,320 reviews) The place was immaculate, beautiful lobby and seating area, crisp clean rooms, everything in order. Reviewed on Oct 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F11%2F2025&endDate=06%2F11%2F2025&selected=10641&PinnedHotelID=10641&HadPinnedHotel=true®ionId=553248635976433381) [See all 891 properties in Kendall County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=553248635976433381) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Kendall County vacation package cost? > Starting from as low as CA $724, 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](https://www.expedia.ca/Chicago-Hotels-Comfort-Inn-Downers-Grove-Lombard.h11297.Hotel-Information) and [Motel 6 Naperville, IL](https://www.expedia.ca/Chicago-Hotels-Motel-6-Naperville.h9225.Hotel-Information). 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](https://www.expedia.ca/service/?langid=4105). 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. ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)