Oswego Vacations from ￥446,202

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    Save up to ￥109,000 when you book a flight and hotel together*

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The Latest Oswego Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Interstate Motel

Interstate Motel

2 out of 5
Price was ￥448,764, price is now ￥446,202 per person
￥446,202
per person
Jan 10 - Jan 13
found 6 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
7.4/10 Good! (22 reviews)
After making a reservation about two weeks in advance, we get there late in the evening to find out they do not have a room available that we reserved. Then, we reluctantly agreed to another room and the smoke smell was so strong. We went to the desk to ask for another room and were told they did not have any other rooms. We had to go to another establishment and find a room. Don’t waste your time.

Reviewed on Mar 28, 2026

Watseka 24 Inn & Suites

Watseka 24 Inn & Suites

2 out of 5
Price was ￥457,818, price is now ￥453,927 per person
￥453,927
per person
Jan 10 - Jan 13
found 6 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
7.4/10 Good! (362 reviews)

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
The price is ￥12,649 per night from Nov 22 to Nov 23
￥12,649
￥13,785 total
Nov 22 - Nov 23
includes taxes & fees
Best Western Oswego Hotel
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is ￥8,983 per night from Dec 14 to Dec 15
￥8,983
￥9,969 total
Dec 14 - Dec 15
includes taxes & fees
7.2/10 Good! (1,904 reviews)
"Breakfast was good for the 1st day same thing every day after that never changed, room needed repairs and paint,had to ask for refills of everything"

Reviewed on Nov 14, 2026

Chicago Club Inn & Suites
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 ￥14,931 per night from Nov 16 to Nov 17
￥14,931
￥16,571 total
Nov 16 - Nov 17
includes taxes & fees
SureStay Plus Hotel by Best Western Chicago Lombard
See all 612 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.

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.
See properties

Frequently asked questions

How much does an Oswego vacation package cost?
You'll find cheap prices from ￥446,202 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.