Oswego Vacation Packages

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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, Hollywood Casino Aurora and Raging Waves Waterpark 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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,135, price is now CA $745 per person
CA $745
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (282 reviews)
The staff were excellent

Reviewed on Aug. 21, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,170, price is now CA $1,307 per person
CA $1,307
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,793, price is now CA $1,090 per person
CA $1,090
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was CA $1,699, price is now CA $1,070 per person
CA $1,070
per person
Oct 6 - Oct 10
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
We loved the experience! We shall come back again😊

Reviewed on Aug. 24, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,291, price is now CA $845 per person
CA $845
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Ready to book your vacation to Oswego?

 

Choose your dates

Oswego Hotel Deals

Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
2055 Wiesbrook Dr, Oswego, IL
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 31 to Sep 1
CA $128
CA $140 total
Aug 31 - Sep 1
includes taxes & fees
Best Western Oswego Hotel
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 $115 per night from Sep 7 to Sep 8
CA $115
CA $128 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (1,102 reviews)
"Restful stay"

Reviewed on Aug. 24, 2025

DoubleTree by Hilton Lisle Naperville
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Sep 16 to Sep 17
CA $99
CA $109 total
Sep 16 - Sep 17
includes taxes & fees
8.8/10 Excellent! (2,203 reviews)
"The facility definitely needs updating, the breakfast was just ok, the location is great, room cleaning only after 3 days is on the short side."

Reviewed on Aug. 25, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
See all 595 properties in Oswego
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

Discover the most popular places to visit in Oswego

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.

Fox Valley Winery

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.

Hudson Crossing Park

Frequently asked questions

How much does an Oswego vacation package cost?
Offering excellent value package deals from CA $745 on Expedia, you'll be surprised at how little a vacation to Oswego costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oswego?
January, February and November are great times to look for cheap Oswego vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on accommodations and flights.
How many days is enough for Oswego?
Usually, a few days is great for an Oswego vacation. With a carefully crafted itinerary, you can go to all the leading sights including Hollywood Casino, as well as discover some hidden gems along the way.
How to find the best Oswego package deals?
Start your search for an Oswego package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oswego package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oswego escape off to a flying start.
Is it cheaper to book an Oswego vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a personalized Oswego vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Oswego?
If you're considering an impromptu Oswego trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Oswego?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Oswego.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Oswego.
  3. Decide how long to go away for: Now that you're up to speed on Oswego, you can figure out the perfect length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Oswego vacation package.

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