Title: Kendall County Vacations & Trips 2026 from CA $644 | 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

- ##  
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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](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 vacation destinations in Kendall County

![View along the Fox River.](https://images.trvl-media.com/place/142441/0f2c17dd-13ca-41e6-95b9-5e5017ce4f3e.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Oswego

[](https://expedia.ca/Oswego.d142441.Destination-Travel-Guides)

![Fox River, Silver Springs State Park, Yorkville, Illinois USA](https://images.trvl-media.com/place/602761/05f326af-3c55-4e46-9936-76d59203385b.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Yorkville

[](https://expedia.ca/Yorkville.d602761.Destination-Travel-Guides)

## Top Kendall County Vacation Deals

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

![Chicago Marriott Downtown Magnificent Mile](https://images.trvl-media.com/lodging/1000000/20000/18100/18035/efd0770d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chicago Marriott Downtown Magnificent Mile

Downtown Chicago

CA $644

per person

May 22 - May 24

found 2 hours ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

8.8/10 Excellent! (1,001 reviews)

We didn’t get the room we thought we booked. Very disappointing. The staff was nice but said this happens a lot because third party reservations. We DO NOT like booking through any place but directly through the hotel. Customer service has definitely changed over the years. We used to like Marriott but because of this we try and book at smaller hotels who answers their phones and makes their own reservations.

Reviewed on Apr 3, 2026

![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,154

per person

Jun 18 - Jun 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant.

Reviewed on Apr 4, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,284

per person

May 23 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,005 reviews)

The staff were wonderful, the room was beautiful, and the location was fantastic. I really wanted to love this hotel. Unfortunately, two issues made for a difficult stay. The noise was severe. Despite being listed as soundproof, our junior suite on the 10th floor was incredibly loud. We’ve stayed in many major cities (and lived in some). But have not experienced this level of disruption from sirens, car alarms, horns, and blasting music from passersby all night. The blackout curtains are thin and don't reach the floor, offering little sound buffering. This is a far cry from the double-glazed windows and heavy drapes you'd expect from a hotel marketing itself as soundproof. The motion-sensor system controlling all lights and HVAC was also a safety concern. If you're still for too long (say, soaking in the bathtub), the entire room goes pitch black. Even the bathroom night light turns off on a timer. We asked the staff to disable this, and they said they did, but the problem persisted. For the price of a 5-star hotel, these issues brought the experience down to a 3-star stay. It's a shame, because so much else was genuinely excellent. We’d return, but only if these issues are addressed.

Reviewed on Apr 5, 2026

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $860

per person

May 23 - May 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (876 reviews)

Nice and clean. Great view. A few construction issues.

Reviewed on Apr 4, 2026

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,471

per person

May 23 - May 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,007 reviews)

Room service took too long

Reviewed on Apr 5, 2026

## 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 $108

CA $120 total

Apr 8 - Apr 9

includes taxes & fees

7.2/10 Good! (1,494 reviews)

.

Reviewed on Apr 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=8492&PinnedHotelID=8492&HadPinnedHotel=true&regionId=553248635976433381)

![Red Roof Inn PLUS+ Chicago - Willowbrook](https://images.trvl-media.com/lodging/1000000/10000/4100/4013/2539e456_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

Fully refundableReserve now, pay when you stay

CA $79

CA $89 total

Apr 12 - Apr 13

includes taxes & fees

6.4/10 (1,085 reviews)

Yes

Reviewed on Apr 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=4013&PinnedHotelID=4013&HadPinnedHotel=true&regionId=553248635976433381)

![Embassy Suites by Hilton Chicago Lombard Oak Brook](https://images.trvl-media.com/lodging/1000000/20000/17400/17328/3e582665_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Lombard Oak Brook

707 E Butterfield Road Lombard IL

Fully refundableReserve now, pay when you stay

CA $182

CA $202 total

Apr 8 - Apr 9

includes taxes & fees

8.2/10 Very Good! (1,474 reviews)

The room had a smell like someone smoked there. Breakfast was great.

Reviewed on Apr 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=17328&PinnedHotelID=17328&HadPinnedHotel=true&regionId=553248635976433381)

[See all 816 properties in Kendall County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&regionId=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?

### How do I get a cheap travel package to Kendall County?

### What are the top hotels in Kendall County?

### How far in advance should I book my Kendall County vacation?

### What does an Expedia Kendall County travel package include?

### What should I know before booking a Kendall County travel package?

### Can I choose my airline with a Kendall County Expedia vacation package?

### If I'm not able to travel, can I cancel my Kendall County vacation package?

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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