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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $2,128, price is now CA $1,457 per person
CA $1,457
per person
Oct 16 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.2/10 Very good! (2,854 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $3,101, price is now CA $1,939 per person
CA $1,939
per person
Oct 16 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $7,890, price is now CA $4,967 per person
CA $4,967
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,229, price is now CA $1,547 per person
CA $1,547
per person
Oct 16 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,779, price is now CA $1,987 per person
CA $1,987
per person
Aug 30 - Sep 5
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
We had such a great stay! Only complaint was one of the blinds would not shut in one of the bedrooms, but we understood it was probably not fixable in the 2 days we were there. We were also upgraded to a better room upon arrival! Overall 10/10!

Reviewed on Jul 23, 2026

Ready to book your vacation to Oswego?

 

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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 $123 per night from Aug 2 to Aug 3
CA $123
CA $134 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (987 reviews)
"Breakfast was better this Sunday"

Reviewed on Jul 26, 2026

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 $121 per night from Aug 20 to Aug 21
CA $121
CA $135 total
Aug 20 - Aug 21
includes taxes & fees
7.8/10 Good! (1,382 reviews)
"Great experience the whole weekend"

Reviewed on Jul 27, 2026

DoubleTree by Hilton Lisle Naperville
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Aug 2 to Aug 3
CA $184
CA $204 total
Aug 2 - Aug 3
includes taxes & fees
8.2/10 Very good! (1,724 reviews)
"The rooms were a nice size with ample supplies. The nightly reception and breakfast were a nice bonus"

Reviewed on Jul 26, 2026

Embassy Suites by Hilton Chicago Lombard Oak Brook
See all 610 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
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Stay near popular Oswego attractions

Hudson Crossing Park

6.0/10 (4 reviews)
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.
See properties

Frequently asked questions

How much does an Oswego vacation package cost?
Offering excellent value package deals from CA $1,457 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.

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.