Oswego Holidays from AU$3,630

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$3,764, price is now AU$3,630 per person
AU$3,630
per person
8 Dec - 11 Dec
found 1 day ago
Return direct flight included
Perth (PER) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on 26 Oct 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was AU$3,960, price is now AU$3,789 per person
AU$3,789
per person
8 Dec - 11 Dec
found 1 day ago
Return direct flight included
Perth (PER) to Chicago (ORD)
9.4/10 Exceptional! (2,727 reviews)

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$4,047, price is now AU$3,894 per person
AU$3,894
per person
8 Dec - 11 Dec
found 1 day ago
Return direct flight included
Perth (PER) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was AU$3,932, price is now AU$3,799 per person
AU$3,799
per person
8 Dec - 11 Dec
found 1 day ago
Return direct flight included
Perth (PER) to Chicago (ORD)
9.2/10 Wonderful! (479 reviews)

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was AU$3,864, price is now AU$3,739 per person
AU$3,739
per person
8 Dec - 11 Dec
found 1 day ago
Return direct flight included
Perth (PER) to Chicago (ORD)
9.4/10 Exceptional! (2,419 reviews)

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$123 per night from 1 Nov to 2 Nov
AU$123
1 Nov - 2 Nov
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 AU$107 per night from 2 Nov to 3 Nov
AU$107
2 Nov - 3 Nov
includes taxes & fees
7.2/10 Good! (1,890 reviews)
"The property itself is very rundown not modern at all. When you enter the property, it smelled like marijuana. There were tons of supplies everywhere almost as if a renovation was going to happen. No one ever checked to see if we needed additional towels, the lighting in the room was horrible. There ..."

Reviewed on 26 Oct 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 AU$153 per night from 3 Nov to 4 Nov
AU$153
3 Nov - 4 Nov
includes taxes & fees
SureStay Plus Hotel by Best Western Chicago Lombard
See all 615 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

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 holiday package cost?
You'll find cheap prices from AU$3,630 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.