Oswego Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Anthony Martinez
    deals illustration

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Oswego Vacation Packages

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 ₩127,594 per night from Jul 20 to Jul 21
₩127,594
₩139,052 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (696 reviews)
"The property is a little tired, but overall it is clean and in good repair. My room had a musty smell that mostly went away once I ran the air conditioner for a while."

Reviewed on Jul 9, 2025

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 ₩114,580 per night from Jul 20 to Jul 21
₩114,580
₩127,161 total
Jul 20 - Jul 21
includes taxes & fees
7.8/10 Good! (1,018 reviews)
"It was a very nice hotel. We really enjoyed our stay."

Reviewed on Jul 8, 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 ₩111,192 per night from Jul 14 to Jul 15
₩111,192
₩123,401 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (2,112 reviews)
"Great!!"

Reviewed on Jul 11, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
See all 597 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.

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?
You'll find cheap prices on Expedia for your Oswego escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Oswego costs.
What are the cheapest months to go to Oswego?
January, February and November are the best times to look for cheap Oswego vacation packages. Opting to travel in quieter months means you can typically find better prices on flights and hotels.
How many days is enough for Oswego?
With a well-organized travel plan, you can easily tick off the most popular Oswego attractions in a few days. But if you'd like to venture off the beaten track or take day trips, think about booking your Oswego vacation for longer.
How to find the best Oswego package deals?
Start your search for an Oswego package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Oswego package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oswego adventure underway.
Is it cheaper to book an Oswego vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a personalized Oswego vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Oswego?
If you're planning an impromptu Oswego adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Oswego?

  1. Choose when to travel: Check your schedule and get packing. Your favorite time of year and the activities on offer will also help you decide when to escape to Oswego.
  2. Set a budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Oswego. Then, choose a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Decide your trip length: Think about how much time you want to spend exploring Oswego. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find an Oswego vacation package that brings all your bookings together.

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