Oswego Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Oswego

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,923, price is now €1,235 per person
€1,235
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Perfect location,superb breakfast buffet, rooftop bar was outstanding and a great option for happy hour!!! We will definitely stay here again on our next trip to Chicago

Reviewed on 24 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €2,285, price is now €1,543 per person
€1,543
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9/10 Wonderful! (504 reviews)
We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure.

Reviewed on 23 Jul 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 €2,344, price is now €1,628 per person
€1,628
per person
6 Oct - 11 Oct
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,855, price is now €1,295 per person
€1,295
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)
Will be back great experience room was amazing.

Reviewed on 23 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was €2,096, price is now €1,474 per person
€1,474
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
We had such a great stay! Only complaint was one of the blinds would not shut in one of the bedrooms, but we understood it was probably not fixable in the 2 days we were there. We were also upgraded to a better room upon arrival! Overall 10/10!

Reviewed on 23 Jul 2026

Top hotels in Oswego

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 €83 per night from 23 Aug to 24 Aug
€83
23 Aug - 24 Aug
includes taxes & fees
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 €84 per night from 19 Aug to 20 Aug
€84
19 Aug - 20 Aug
includes taxes & fees
DoubleTree by Hilton Lisle Naperville
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 €58 per night from 23 Aug to 24 Aug
€58
23 Aug - 24 Aug
includes taxes & fees
7.2/10 Good! (1,667 reviews)
"Very friendly and clean, food is good and excellent customer service!"

Reviewed on 23 Jul 2026

Chicago Club Inn & Suites
See all 571 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 holiday package cost?
You'll find cheap prices from €1,235 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.