Oswego Vacations from $142

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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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $278, price is now $142 per person
$142
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $719, price is now $364 per person
$364
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe.

Reviewed on Nov 22, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $680 per person
$680
per person
Dec 27 - Jan 2
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.

Reviewed on Nov 25, 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $285, price is now $159 per person
$159
per person
Jan 17 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.2/10 Exceptional! (2,008 reviews)
Great accommodation!

Reviewed on Nov 19, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $398, price is now $222 per person
$222
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (1,862 reviews)
Superb in all respects. Will stay again for sure.

Reviewed on Nov 20, 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.

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

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
$75 nightly
The price is $82 total per night from Nov 30 to Dec 1
$82 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (771 reviews)
Very clean room and hotel, friendly staff, had all amenities needed.

Reviewed on Nov 10, 2025

Best Western Oswego Hotel
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
$72 nightly
The price is $80 total per night from Nov 26 to Nov 27
$80 total
Nov 26 - Nov 27
Total with taxes and fees
8.8/10 Excellent! (2,394 reviews)
Clean room friendly staff and great breakfast in a great location

Reviewed on Nov 23, 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
$60 nightly
The price is $66 total per night from Dec 25 to Dec 26
$66 total
Dec 25 - Dec 26
Total with taxes and fees
7/10 Good! (1,328 reviews)
Clean room. Proximity to the highway and good restaurants.

Reviewed on Nov 16, 2025

Chicago Club Inn & Suites
See all 613 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.

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 $142 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.