Title: Oswego Vacation Packages & Trips 2026 from CA $1,281 | Expedia.ca

[Hotels in Oswego](https://expedia.ca/Oswego-Hotels.d142441.Travel-Guide-Hotels)[Vacation Rentals in Oswego](https://expedia.ca/Oswego-Vacation-Rentals.d142441.Travel-Guide-VacationRentals)[Flights to Oswego](https://expedia.ca/Cheap-Flights-To-Oswego.d142441.Travel-Guide-Flights)[Oswego Car Rentals](https://expedia.ca/Car-Rentals-In-Oswego.d142441.Car-Rental-Guide)

![](https://images.trvl-media.com/place/142441/0f2c17dd-13ca-41e6-95b9-5e5017ce4f3e.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Oswego Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
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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
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Rest easy  
Plan, book, and manage your trip all in one place

#### Your Oswego Vacation

Our vacation packages to Oswego offer countless opportunities to enjoy new sights, sounds and smells. And with all of the travel arrangements taken care of, you can breathe easy and enjoy your city escape in the way that you deserve. [Aurora University](https://www.expedia.ca/Aurora-University-Aurora.d6129538.Vacation-Attraction), [Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Aurora.d6260166.Vacation-Attraction) and [Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Yorkville.d553248621532658485.Vacation-Attraction) are just a few of the many attractions worth checking out during your trip to Oswego. Expedia is here to help you escape your routine. Tailor your vacation to Oswego to suit your travel style, whatever that may be!

## Top Oswego Vacation Deals

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

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,281

per person

Jun 4 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (3,438 reviews)

Good breakfast, excellent service, unfortunately, they don't have microwave service to heat food

Reviewed on Mar 13, 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 $1,564

per person

May 28 - May 31

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,385 reviews)

The room so clean with a beautiful view!

Reviewed on Mar 13, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,658

per person

Jun 5 - Jun 8

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (414 reviews)

This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back.

Reviewed on Mar 8, 2026

![Hyatt Place Chicago/Downtown - The Loop](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

CA $1,320

per person

Jun 4 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

8.8/10 Excellent! (1,201 reviews)

We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.

Reviewed on Mar 9, 2026

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $1,366

per person

Jun 4 - Jun 7

found 9 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (1,137 reviews)

Great location, clean and very nice restaurant and bar.

Reviewed on Mar 9, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_142441)

## Ready to book your vacation to Oswego?

Choose your dates

## Oswego Hotel Deals

![Best Western Oswego Hotel](https://images.trvl-media.com/lodging/1000000/430000/424400/424318/4e4a11b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Best Western Oswego Hotel

2055 Wiesbrook Dr Oswego IL

Fully refundableReserve now, pay when you stay

CA $100

CA $109 total

Mar 15 - Mar 16

includes taxes & fees

8.8/10 Excellent! (855 reviews)

Second time at this hotel, it's a good value for the money. The staff is wonderful, very helpful and professional, good Wi-Fi and quiet for the most part. Super clean! There is a wide selection of breakfast choices (i wasnt impressed with the eggs) and a fitness room with a couple of cardio machines. ...

Reviewed on Mar 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=424318&PinnedHotelID=424318&HadPinnedHotel=true&regionId=142441)

![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 $106 total

Mar 19 - Mar 20

includes taxes & fees

7.2/10 Good! (1,473 reviews)

The building caught fire while staying there. Every terrifying experience.

Reviewed on Mar 9, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F03%2F2026&endDate=20%2F03%2F2026&selected=8492&PinnedHotelID=8492&HadPinnedHotel=true&regionId=142441)

![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 $77

CA $87 total

Mar 28 - Mar 29

includes taxes & fees

6.4/10 (1,064 reviews)

Don't go there, it it really smell

Reviewed on Mar 11, 2026

[](https://expedia.ca/Hotel-Search?startDate=28%2F03%2F2026&endDate=29%2F03%2F2026&selected=4013&PinnedHotelID=4013&HadPinnedHotel=true&regionId=142441)

[See all 611 properties in Oswego](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F03%2F2026&endDate=15%2F03%2F2026&regionId=142441)

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)

### Discover the most popular places to visit in Oswego

![railway trestle bridge over wallkill river valley](https://images.trvl-media.com/place/553248621532658491/83afbe63-200d-4261-bc9e-ef33fb6ab5d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Hudson Crossing Park

Explore the great outdoors at Hudson Crossing Park, a lovely green space in Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries. 

[](https://expedia.ca/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction)

#### Fox Valley Winery

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. 

[](https://expedia.ca/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction)

## Explore a world of travel with Expedia

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- [Hudson Crossing Park ](https://www.expedia.ca/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction)
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- [Yorktown Shopping Center ](https://www.expedia.ca/Yorktown-Shopping-Center-Chicago.d6227539.Vacation-Attraction)
- [Yorkville Vacations ](https://www.expedia.ca/Yorkville.d602761.Destination-Travel-Guides)

- [Car rentals in Budget 1426 State Route 66 Ste 101 ](https://www.expedia.ca/Budget-at-1426-State-Route-66-Ste-101-Flagstaff-Arizona-USA.v6186.Car-Rental-Guide-Location)
- [Car rental Aurora ](https://www.expedia.ca/Car-Rentals-In-Aurora.d6186.Car-Rental-Guide)
- [Car rental Yorkville ](https://www.expedia.ca/Car-Rentals-In-Yorkville.d602761.Car-Rental-Guide)
- [Hertz Rental Cars in Aurora ](https://www.expedia.ca/Hertz-Car-Rentals-In-Aurora.d6186-c40.Car-Rental-Guide-Suppliers)

- [Aurora Vacation Rentals ](https://www.expedia.ca/Aurora-Vacation-Rentals.d6186.Travel-Guide-VacationRentals)

\* 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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