Oswego Vacations from $336

Book a Hotel + Flight or Car together to unlock savings

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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.
Swissotel - Chicago
Hotel Riu Plaza Chicago
Pendry Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Trump International Hotel & Tower Chicago
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Oswego Hotel Deals

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
$84 nightly
The price is $93 total per night from Oct 16 to Oct 17
$93 total
Oct 16 - Oct 17
Total with taxes and fees
8.8/10 Excellent! (2,286 reviews)
"Ver"

Reviewed on Oct 8, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Oct 21 to Oct 22
$80 total
Oct 21 - Oct 22
Total with taxes and fees
7/10 Good! (1,267 reviews)
"Very good location, convenient to Oakbrook shopping center and West Suburbs. Great value"

Reviewed on Oct 6, 2025

Chicago Club Inn & Suites
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
$124 nightly
The price is $130 total per night from Oct 13 to Oct 14
$130 total
Oct 13 - Oct 14
Total with taxes and fees
8.4/10 Very Good! (1,273 reviews)
"The staff was friendly, room was perfect for the occasion."

Reviewed on Oct 5, 2025

The Champagne Lodge & Luxury Suites
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.

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 $336 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.

Explore a world of travel with Expedia

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.