Oswego Holidays from AU$2,912

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Your Oswego Holiday

With a holiday package to Oswego, say goodbye to travel planning and hello to trouble-free adventure. Every detail of your escape has been taken care of before you depart, so you can get on with discovering this lively city. Eager to do a bit of sightseeing? A trip to Oswego isn't complete without checking out Fox Valley Winery, Hudson Crossing Park and other big-ticket attractions. Browse Expedia's extensive range of travel options and begin planning your perfect holiday to Oswego today.

The Latest Oswego Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Spark by Hilton Merrillville

Spark by Hilton Merrillville

3 out of 5
Price was AU$2,957, price is now AU$2,912 per person
AU$2,912
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (52 reviews)
Excellent all around, very nice place to stay.

Reviewed on 24 Aug. 2025

Hilton Garden Inn Merrillville

Hilton Garden Inn Merrillville

3 out of 5
Green Acres
Price was AU$3,547, price is now AU$3,196 per person
AU$3,196
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The staff were absolutely wonderful. Everything was clean and they had an open bar and the bartender was absolutely amazing. The lady at the front desk couldn’t have been more helpful. It had been a long trip and they were right there, waiting on us hand and foot.

Reviewed on 19 Aug. 2025

Hampton Inn by Hilton Merrillville

Hampton Inn by Hilton Merrillville

2.5 out of 5
Price was AU$3,115, price is now AU$2,930 per person
AU$2,930
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (805 reviews)
Convenient to shops and restaurants.

Reviewed on 2 Aug. 2025

Tru By Hilton Merrillville

Tru By Hilton Merrillville

2.5 out of 5
Price was AU$3,074, price is now AU$3,020 per person
AU$3,020
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (273 reviews)
Property was clean and the staff was outstanding.

Reviewed on 26 Aug. 2025

Homewood Suites by Hilton Munster

Homewood Suites by Hilton Munster

3 out of 5
Price was AU$3,033, price is now AU$2,981 per person
AU$2,981
per person
27 Sept - 4 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
I love how kind the staff was , they were amazing!

Reviewed on 22 Aug. 2025

Oswego Holiday

Oswego Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
34,000
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Raging Waves Waterpark, Paramount Theatre and Splash Country Waterpark

Our pick of the best 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
The price is AU$155 per night from 2 Sept to 3 Sept
AU$155
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (727 reviews)
"Close to family and services."

Reviewed on 26 Aug. 2025

Best Western Oswego Hotel
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is AU$142 per night from 28 Sept to 29 Sept
AU$142
28 Sept - 29 Sept
includes taxes & fees
7.8/10 Good! (1,098 reviews)
"This was a horrible experience. The bedding was dirty and stained.. basically used. They provided a new room which smelled so bad we had to check out . The smell made my eyes & throat hurt and my daughter was getting a headache from the smell. We checked out and left the hotel. They said they would ..."

Reviewed on 19 Aug. 2025

DoubleTree by Hilton Lisle Naperville
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 AU$121 per night from 16 Sept to 17 Sept
AU$121
16 Sept - 17 Sept
includes taxes & fees
8.8/10 Excellent! (2,204 reviews)
"The facility definitely needs updating, the breakfast was just ok, the location is great, room cleaning only after 3 days is on the short side."

Reviewed on 25 Aug. 2025

SureStay Plus Hotel by Best Western Chicago Lombard
See all 595 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Oswego holiday package cost?
You'll find cheap prices from AU$2,912 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 holiday 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 holiday 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-organised 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 holiday 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 holiday as a package?
Expedia holiday 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 personalised Oswego holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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 favourite 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 holiday 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.