Oswego Vacation Packages

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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!

Top Oswego Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was CA $1,069, price is now CA $777 per person
CA $777
per person
Sep 11 - Sep 14
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
Nice setup, courteous staff, wasn’t expecting to have to pay $100 deposit on top of the money I paid Expedia, also an additional fee of $17 that Expedia did not cover even though they summed up all the charges before our stay. Seems to be a consistent issue with Expedia.

Reviewed on Jul 15, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,113, price is now CA $1,436 per person
CA $1,436
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,178, price is now CA $800 per person
CA $800
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
I wish the space was bigger. It was too tight for me and my young girls but the staff was so extra nice and welcoming.

Reviewed on Jul 14, 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $1,458, price is now CA $1,029 per person
CA $1,029
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I enjoyed my stay here. Clean room, well maintained property and great location just 3 miles from Chicago. The best part was the friendly staff. The breakfast was a 4.5 out 5, just adequate foe the day's need, nothing super special. I would definitely return.

Reviewed on Jul 13, 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 CA $1,339, price is now CA $965 per person
CA $965
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Overall very satisfied with the service. Location is top notch. Just a stone throw away from lots of activities.

Reviewed on Jul 15, 2026

Ready to book your vacation to Oswego?

 

Choose your dates

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 CA $134 per night from Aug 10 to Aug 11
CA $134
CA $146 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (975 reviews)
"Very nice stay. Check in was easy, and the room was clean and comfortable. Nice breakfast in the morning, with many options. The staff is always helpful, especially Jenny at the front desk."

Reviewed on Jul 14, 2026

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 CA $106 per night from Jul 21 to Jul 22
CA $106
CA $118 total
Jul 21 - Jul 22
includes taxes & fees
7.2/10 Good! (1,654 reviews)
"The hotel was not well maintained. Not cleaned to the fullest. The owner of the hotel was being rude to people and coming to their room with a hour left until check out to tell them they need to leave. Just wasn’t a good experience at all."

Reviewed on Jul 15, 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 CA $136 per night from Aug 4 to Aug 5
CA $136
CA $151 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (2,876 reviews)
"Clean!!"

Reviewed on Jul 15, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
See all 574 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.
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Stay near popular Oswego attractions

Hudson Crossing Park

6.0/10 (4 reviews)
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.
See properties

Frequently asked questions

How much does an Oswego vacation package cost?
Offering excellent value package deals from CA $777 on Expedia, you'll be surprised at how little a vacation to Oswego costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oswego?
January, February and November are great times to look for cheap Oswego vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on accommodations and flights.
How many days is enough for Oswego?
Usually, a few days is great for an Oswego vacation. With a carefully crafted itinerary, you can go to all the leading sights including Hollywood Casino, as well as discover some hidden gems along the way.
How to find the best Oswego package deals?
Start your search for an Oswego package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oswego package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oswego escape off to a flying start.
Is it cheaper to book an Oswego vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a personalized Oswego vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Oswego?
If you're considering an impromptu Oswego trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Oswego?

  1. Choose when to go: Check your diary and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Oswego.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Oswego.
  3. Decide how long to go away for: Now that you're up to speed on Oswego, you can figure out the perfect length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Oswego vacation package.

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.