Title: Oswego Vacation Packages & Trips 2025/2026 from CA $405 | Expedia.ca [Hotels in Oswego](https://expedia.ca/Oswego-Hotels.d142441.Travel-Guide-Hotels)[Vacation Rentals in Oswego](https://expedia.ca/Oswego-Vacation-Rentals.d142441.Travel-Guide-VacationRentals)[Flights to Oswego](https://expedia.ca/Cheap-Flights-To-Oswego.d142441.Travel-Guide-Flights)[Oswego Car Rentals](https://expedia.ca/Car-Rentals-In-Oswego.d142441.Car-Rental-Guide) ![](https://images.trvl-media.com/place/142441/b120e67f-cbdd-4376-a78c-263755ddd72d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oswego Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Anthony Martinez - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Aurora-University-Aurora.d6129538.Vacation-Attraction), [Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Aurora.d6260166.Vacation-Attraction) and [Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Yorkville.d553248621532658485.Vacation-Attraction) 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. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $405 per person Jan 17 - Jan 20 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=92d7CaqPSq2GV42U8ooj1eBrInoJikFc6aSwjyF6usuFVe04ke_yhiSybK1mDTJO) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $495 per person Jan 17 - Jan 20 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=92d7CaqPSq2GV42U8ooj1RJwHDnBvEA_ukdTSDxRaGwSRyi2TNXnvnh8nGHEfQle) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,565 per person Dec 28 - Jan 2 found 19 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=VCE7QcuKn8xLCDGDCnmXgJdnWyYNrlV6tflwfANmWgVQAqJQQm4cwjPjGnSiA_Yz) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $912 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (367 reviews) We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue. However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic). Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=j8BypNWI3qNytJIf8GYV9UBu_rWWQXjGDKG7xJBh7fxe98WWwVs7BAqRZgab2VL3) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $466 per person Jan 17 - Jan 20 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.2/10 Wonderful! (303 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=92d7CaqPSq2GV42U8ooj1RJwHDnBvEA_ukdTSDxRaGxxicyqzSnMsJ-3kd93J78T) ## Ready to book your vacation to Oswego? Choose your dates ## Oswego Hotel Deals ![Best Western Oswego Hotel](https://images.trvl-media.com/lodging/1000000/430000/424400/424318/7b695b40_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Oswego Hotel 2055 Wiesbrook Dr, Oswego, IL Fully refundableReserve now, pay when you stay CA $105 CA $115 total Nov 2 - Nov 3 includes taxes & fees 8.6/10 Excellent! (755 reviews) Great Reviewed on Oct 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=424318&PinnedHotelID=424318&HadPinnedHotel=true®ionId=142441) ![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/w3838h2556x2y3-00664b38_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay Plus Hotel by Best Western Chicago Lombard 222 E 22nd Street, Lombard, IL Fully refundableReserve now, pay when you stay CA $113 CA $125 total Oct 26 - Oct 27 includes taxes & fees 8.8/10 Excellent! (2,319 reviews) This hotel is under renovation . Clean lobby , clean room . Excellent front desk workers . Very accommodating! Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=10641&PinnedHotelID=10641&HadPinnedHotel=true®ionId=142441) ![Chicago Club Inn & Suites](https://images.trvl-media.com/lodging/1000000/10000/8500/8492/02be5769_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chicago Club Inn & Suites 630 Pasquinelli Dr, Westmont, IL Fully refundableReserve now, pay when you stay CA $95 CA $106 total Nov 23 - Nov 24 includes taxes & fees 7/10 Good! (1,298 reviews) Perfect for our stay Reviewed on Oct 21, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=8492&PinnedHotelID=8492&HadPinnedHotel=true®ionId=142441) [See all 601 properties in Oswego](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=142441) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Oswego #### 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. [](https://expedia.ca/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction) #### 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. [](https://expedia.ca/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental ### Lodging - [Farmstay in Aurora](https://www.expedia.ca/Aurora-Agritourism.d6186-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Aurora](https://www.expedia.ca/Aurora-Apart-Hotels.d6186-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Aurora](https://www.expedia.ca/Aurora-Bed-And-Breakfast.d6186-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Aurora](https://www.expedia.ca/Aurora-Castles.d6186-aaCastles.Travel-Guide-Accommodation) - [Chalets in Aurora](https://www.expedia.ca/Aurora-Chalets.d6186-aaChalets.Travel-Guide-Accommodation) - [Cruise Ships in Aurora](https://www.expedia.ca/Aurora-Cruise-Ships.d6186-aaCruiseShips.Travel-Guide-Accommodation) - [Guest Houses in Aurora](https://www.expedia.ca/Aurora-Guest-Houses.d6186-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Aurora](https://www.expedia.ca/Aurora-Holiday-Parks.d6186-aaHolidayParks.Travel-Guide-Accommodation) - 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[Cedardell Golf Club](https://www.expedia.ca/Cedardell-Golf-Club-Plano.d553248621532658481.Vacation-Attraction) - [Centennial Beach](https://www.expedia.ca/Centennial-Beach-Chicago.d553248621532658519.Vacation-Attraction) - [Elgin Vacations](https://www.expedia.ca/Elgin.d7817.Destination-Travel-Guides) - [Elmhurst Vacations](https://www.expedia.ca/Elmhurst.d7836.Destination-Travel-Guides) - [Farnsworth House](https://www.expedia.ca/Farnsworth-House-Plano.d553248621532658479.Vacation-Attraction) - [Fox Valley Winery](https://www.expedia.ca/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction) - [Geneva Commons](https://www.expedia.ca/Geneva-Commons-Geneva.d6260155.Vacation-Attraction) - [Hillside Vacations](https://www.expedia.ca/Hillside.d8353.Destination-Travel-Guides) - [Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Aurora.d6260166.Vacation-Attraction) - [Hollywood Casino](https://www.expedia.ca/Hollywood-Casino-Aurora.d6065135.Vacation-Attraction) - [Hudson Crossing Park](https://www.expedia.ca/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction) - [Joliet Vacations](https://www.expedia.ca/Joliet.d8116.Destination-Travel-Guides) - [Lewis University](https://www.expedia.ca/Lewis-University-Romeoville.d6146844.Vacation-Attraction) - [Morton Arboretum](https://www.expedia.ca/Morton-Arboretum-Chicago.d6238155.Vacation-Attraction) - [Now Arena](https://www.expedia.ca/NOW-Arena-Chicago.d6192396.Vacation-Attraction) - [Otter Cove Aquatic Park](https://www.expedia.ca/Otter-Cove-Aquatic-Park-St-Charles.d553248621532658533.Vacation-Attraction) - [Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Yorkville.d553248621532658485.Vacation-Attraction) - [Santa's Village](https://www.expedia.ca/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction) - [Schaumburg Vacations](https://www.expedia.ca/Schaumburg.d8107.Destination-Travel-Guides) - [Seneca Vacations](https://www.expedia.ca/Seneca.d3000435306.Destination-Travel-Guides) - 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