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.
Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,068, price is now CA $763 per person
CA $763
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (406 reviews)
I believe the staff was very attentive.
Reviewed on Jun 9, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $3,367, price is now CA $2,156 per person
CA $2,156
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Lodge Geneva National
Price was CA $2,221, price is now CA $1,517 per person
CA $1,517
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,372 reviews)
The Lodge was under construction when we stayed there so it was a little dusty - mainly outdoors.
My room was just off the lobby. The noise from the lobby overflowed to my room until they closed the fire doors. I would recommend they close them earlier ~ 9 pm.
Reviewed on Jun 8, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,605, price is now CA $1,860 per person
CA $1,860
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Unfortunately the elevators were out, at no fault of the staff. They were fantastic at trying to give the best service possible. The room was beautiful with a breathtaking view of the lake.
Reviewed on Jun 10, 2026
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
Price was CA $1,575, price is now CA $1,135 per person
CA $1,135
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,007 reviews)
The amenities and size of the rooms were wonderful. The photos of the rooms were misleading. The water park is an additional fee, but it’s the main photo for the whole hotel? Bait and switch. The floors in the room and generally on the property were dirty. Elevator was gross. Beds were comfortable.
The staff at the Grand Geneva were helpful, but you are not a Grand Geneva guest, you are a Holiday Inn guest and they are not connected. No Holiday Inn staff on site.
Reviewed on Jun 5, 2026
Oswego Hotel Deals
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Jul 5 to Jul 6
CA $110
CA $120 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (931 reviews)
"Not good place"
Reviewed on Jun 10, 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 $128 per night from Jun 21 to Jun 22
CA $128
CA $142 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (2,793 reviews)
"Everything was perfect"
Reviewed on Jun 10, 2026
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jun 28 to Jun 29
CA $159
CA $177 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (1,624 reviews)
"I was very happy with just about everything at the embassy suites. My room was large, comfortable clean. It had everything I needed. The breakfast in the morning was absolutely amazing. It had delicious food all fresh cooked. I would definitely stop here again"
Reviewed on Jun 11, 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.
