Oswego Vacations from $385
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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!
The Latest Oswego vacation packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,027
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
$536
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
The bathroom needs to be updated! The tub is difficult getting in and out of it for older adults
Reviewed on Oct 2, 2026
Stay near popular Oswego attractions
Hudson Crossing Park
6.0/10 (4 reviews)
A riverside sanctuary with accessible playgrounds, ziplines, and serene picnic spots along the Fox River. Explore the Egret sculpture garden or cross the pedestrian bridge for peaceful views of Waubonsie Creek.
Fox Valley Winery
6.8/10 (5 reviews)
Fox Valley Winery showcases wines from grapes grown along the scenic Fox River Valley. Sample their diverse selection in the tasting room while admiring local artwork on display.
Keller's Farmstand
This family-run farmstand offers seasonal delights from apple picking to a corn maze. Savor homegrown produce and fresh-baked treats while enjoying authentic farm activities during the vibrant fall festivities.
Oswego Hotel Deals
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
$79 nightly
$86 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
$86 nightly
$96 total
Oct 18 - Oct 19
Total with taxes and fees
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
$52 nightly
$58 total
Nov 2 - Nov 3
Total with taxes and fees
7.2/10 Good! (1,842 reviews)
"Good deal for jetted tub room. Quite far from downtown but still close to local amenities. Gas station within 2 minute walking distance."
Reviewed on Oct 2, 2026
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.
Find the Best Oswego Vacation Packages
Oswego Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 34,000 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Fox Valley Winery, Farnsworth House and Hudson Crossing Park |
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Frequently asked questions
How much does an Oswego vacation package cost?
You'll find cheap prices from $385 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?
If you're looking to book a cheap Oswego vacation package, consider visiting in January, February and March. You'll usually find lower rates on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Oswego?
With a well-planned schedule, you can easily hit the main Oswego sights in a few days. But if you'd like to discover lesser-known spots or go on day trips, consider 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.
Does Expedia offer Book Now, Pay Later Oswego vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Oswego break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
