Oswego Vacation Packages 2025/2026 from $217

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

Downtown Chicago

Save 100% on your flight

$336

per person

Nov 13 - Nov 16

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on Oct 9, 2025

Hotel Riu Plaza Chicago

Downtown Chicago

$383

per person

Nov 13 - Nov 16

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,427 reviews)

Absolutely lovely and helpfully staff

Reviewed on Oct 8, 2025

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$349

per person

Nov 13 - Nov 16

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on Oct 7, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$535

per person

Nov 13 - Nov 16

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,142 reviews)

Absolutely loved this place.... views were great, staff was great, atmosphere was great! One of my most favorite places to stay.

Reviewed on Oct 8, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

$555

per person

Dec 13 - Dec 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

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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.

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.

Oswego Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street, Lombard, IL

Fully refundableReserve now, pay when you stay

$84 nightly

$93 total

Oct 16 - Oct 17

Total with taxes and fees

8.8/10 Excellent! (2,286 reviews)

"Ver"

Reviewed on Oct 8, 2025

Chicago Club Inn & Suites

630 Pasquinelli Dr, Westmont, IL

Fully refundableReserve now, pay when you stay

$72 nightly

$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

The Champagne Lodge & Luxury Suites

16 W 621 S. Frontage Rd, Willowbrook, IL

$124 nightly

$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

See all 605 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.

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.

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

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Oswego Vacations from $336

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Your Oswego Vacation

The Latest Oswego vacation packages

Swissotel - Chicago

Hotel Riu Plaza Chicago

Pendry Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

Trump International Hotel & Tower Chicago

Discover the most popular places to visit in Oswego

Fox Valley Winery

Hudson Crossing Park

Oswego Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

Chicago Club Inn & Suites

The Champagne Lodge & Luxury Suites

Oswego Essential Information

More vacations you might like

Frequently asked questions

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