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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,359, price is now CA $878 per person
CA $878
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.
Reviewed on Apr 24, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,467, price is now CA $1,649 per person
CA $1,649
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
Absolutely fantastic will be back
Reviewed on Apr 27, 2026
Oswego Hotel Deals
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from May 10 to May 11
CA $108
CA $117 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (892 reviews)
Our room was extremely clean and was very comfortable! The bed was great and amenities were wonderful! The entire staff at checkin and breakfast were so friendly and helpful! We couldn’t have asked for a better breakfast-probably the best we’ve had in a hotel! It was in a very convenient location ...
Reviewed on Apr 27, 2026
AmericInn by Wyndham Oswego
1050 Douglas Road Oswego IL
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from May 18 to May 19
CA $156
CA $173 total
May 18 - May 19
includes taxes & fees
8.2/10 Very Good! (560 reviews)
I believe the girl I spoke with was new. Either busy or just didn't care. We were attending a visitation. I asked if our driving time got us there before 3:00 could we check in. Abruptly she said '40.00' You have got to be kidding. The Manager told me this morning we could check in an hour early ...
Reviewed on Apr 20, 2026
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from May 19 to May 20
CA $120
CA $133 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (2,714 reviews)
Clean room. Kind front desk
Reviewed on May 1, 2026
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.
Discover the most popular places to visit in Oswego
Hudson Crossing Park
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.
Fox Valley Winery
You can enjoy a tasting or tour at Fox Valley Winery during your travels to Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries.
Explore a world of travel with Expedia
- Farmstay in Aurora
- Aparthotels in Aurora
- B&B in Aurora
- Castles in Aurora
- Chalets in Aurora
- Cruise Ships in Aurora
- Guest Houses in Aurora
- Holiday Park Resorts in Aurora
- Hostels in Aurora
- Adults Only Resorts & in Aurora
- All Inclusive Resorts and in Aurora
- Beach Hotel Hotels in Aurora
- Boutique Hotels in Aurora
- Casino Hotels in Aurora
- Cheap Hotels in Aurora
- Hotels with Early Check-in in Aurora
- Hotels with a Pool in Aurora
- Hotels with Balconies in Aurora
- Hotels with Free Breakfast in Aurora
- Hotels with Hot Tubs in Aurora
- Hotels with an Indoor Pool in Aurora
- Hotels with Kitchenettes in Aurora
- Hotels with Waterslides in Aurora
- Luxury Hotels in Aurora
- Mountain Hotels in Aurora
- Oceanfront Hotels in Aurora
- Pet-Friendly Hotels in Aurora
- Ski Hotels in Aurora
- Spa Hotels in Aurora
- Waterpark Hotels in Aurora
- Aurora Hotels
- Inns in Aurora
- Lodges in Aurora
- Motels in Aurora
- Pensions in Aurora
- Pousadas in Aurora
- Ranches in Aurora
- Resorts in Aurora
- Riads in Aurora
- Townhomes in Aurora
- Treehouses in Aurora
- Hotels near Aurora University
- Cottages in Boulder Hill
- Vacation Homes in Boulder Hill
- Chicago Hotels
- Hotels near Hollywood Casino Aurora
- Hotels near Hollywood Casino
- Farmstay in Montgomery
- B&B in Montgomery
- Chalets in Montgomery
- Guest Houses in Montgomery
- Cheap Hotels in Montgomery
- Luxury Hotels in Montgomery
- Waterpark Hotels in Montgomery
- Montgomery Hotels
- Inns in Montgomery
- Motels in Montgomery
- Hotels near Paramount Theater
- Hotels near Raging Waves Waterpark
- Luxury Hotels in Yorkville
- Yorkville Hotels
- Arcada Theater
- Broadview Vacations
- Cabela's
- Cedardell Golf Club
- Centennial Beach
- Elgin Vacations
- Elmhurst Vacations
- Farnsworth House
- Fox Valley Winery
- Geneva Commons
- Hillside Vacations
- Hollywood Casino Aurora
- Hollywood Casino
- Hudson Crossing Park
- Joliet Vacations
- Lewis University
- Morton Arboretum
- Now Arena
- Otter Cove Aquatic Park
- Raging Waves Waterpark
- Santa's Village
- Schaumburg Vacations
- Seneca Vacations
- Serena Vacations
- Sheridan Vacations
- Silver Springs State Park
- Splash Country Waterpark
- Wheaton Vacations
- Yorktown Shopping Center
- Yorkville Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
