Oswego Vacations from $664

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,091, price is now $664 per person
$664
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
The front foyer had beautiful glass bulbs that were very dusty and dirty. Not a good first impression Housekeeping or room service could have been disclosed for 4 nights garbage build up Also notice we had no bathroom hooks to hang wet towels just one towel bar. Bed was comfortable and linens were fine. Oh and, $8 bottle of Voss water in room no cups in room or bathroom. Microwave breakfast 😑

Reviewed on Jun 15, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,280, price is now $705 per person
$705
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
The rooftop bar was great.

Reviewed on Jun 17, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,359, price is now $766 per person
$766
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,378 reviews)
The location was amazing though the rooms were a bit run down.

Reviewed on Jun 18, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,299, price is now $735 per person
$735
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,129 reviews)
Great staff. Room was small. Good location.

Reviewed on Jun 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,653, price is now $991 per person
$991
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on Jun 14, 2026

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Stay near popular Oswego attractions

Hudson Crossing Park

6.0/5 (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.
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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
$95 nightly
The price is $104 total per night from Jun 21 to Jun 22
$104 total
Jun 21 - Jun 22
Total with taxes and fees
8.8/10 Excellent! (946 reviews)
"The stay was good everyone is very nice and respectful and helpful"

Reviewed on Jun 17, 2026

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
$92 nightly
The price is $102 total per night from Jun 21 to Jun 22
$102 total
Jun 21 - Jun 22
Total with taxes and fees
9/10 Wonderful! (2,805 reviews)
"Small rooms"

Reviewed on Jun 18, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Jul 12 to Jul 13
$117 total
Jul 12 - Jul 13
Total with taxes and fees
8.2/10 Very Good! (1,638 reviews)
"This hotel was clean, spacious, & cozy and close to a variety of restaurants, bars, & shopping centers."

Reviewed on Jun 17, 2026

Embassy Suites by Hilton Chicago Lombard Oak Brook
See all 614 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 $664 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.